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  • 1995-1999  (591)
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  • 1930-1934
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  • 1
    Electronic Resource
    Electronic Resource
    Cytochemical staining and ultrastructural characteristics of peripheral blood leucocytes from the yellow rat snake (Elaphe obsoleta quadrivitatta) (1996)
    Springer
    Comparative clinical pathology 6 (1996), S. 86-91 
    Details
    ISSN: 1433-2981
    Keywords: Cytochemical staining ; Leucocytes ; Snake ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Cytochemical staining and ultrastructural characteristics of peripheral blood leucocytes from the yellow rat snake are described. A panel of cytochemical stains, including demonstration of myeloperoxidase, acid phosphatase, naphthol AS-D chloracetate esterase, alpha-naphthol butyrate esterase and alkaline phosphatase activities; and periodic acid-Schiff and Sudan Black-B staining was performed. Snake heterophils lacked peroxidase, alkaline phosphatase and acid phosphatase activity. Azurophils stained positively for all stains except alkaline phosphatase activity. Lymphocytes showed positive acid phosphatase activity. Differentiation of thrombocytes from lymphocytes was very difficult even with cytochemical staining. Only a minor staining difference was observed with periodic acid-Schiff stain. Thrombocytes exhibited coarse, dark, purple stippling usually located in the polar area of the cytoplasm, whereas lymphocyte staining varied from none to very fine, pale pink granules dispersed throughout the cytoplasm. Ultrastructural characteristics were similar to those of mammalian leucocytes with the exception that the snake basophil granules have no crystalline matrix, and heterophil granules appeared as large, elongate, membrane bound structures of varying density with no distinct core or matrix.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00426047
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  • 2
    Electronic Resource
    Electronic Resource
    Hochauflösende Rasterelektronenmikroskopie von isolierten äußeren Haarzellen (1996)
    Springer
    HNO 44 (1996), S. 630-633 
    Details
    ISSN: 1433-0458
    Keywords: Schlüsselwörter Innenohr ; Ultrastruktur ; Einzelzelle ; SEM ; Key words Inner ear ; Ultrastructure ; Isolated hair cells ; Scanning electron microscopy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Description / Table of Contents: Summary Isolated hair cell preparations have gained wide acceptance as a model for studying physiological and molecular properties of the sensory cells involved in the hearing process. Ultrastructural details, such as stereocilia links, lateral membrane substructure or synaptic links are of crucial importance for normal sensory transduction. For this reason, we developed a high-resolution scanning electron microscopy (SEM) procedure to study the surface of isolated hair cells. Cells were mechanically and/or enzymatically separated, isolated and immobilized on cover slips by alcian blue and fixed by 2% glutardialdehyde or 1% OsO4. After dehydration, preparations were critical point-dried and sputter-coated with gold-palladium (2–4 nm). Up to 5 nm resolution was achieved. Optimal fixation kept the cells in their typical cylindrical forms. Preservation of the stereocilia and the apical plates of the outer hair cells depended strongly on the fixation process. Tip- and side-links were observed only sporadically because of the aggressive preparation procedure. The lateral plasma membranes of the cell bodies showed regular granular structures of 5–7 nm diameter at maximal magnification. The granular structure of the cell membrane seemed to correspond to putataive transmembrane proteins believed to generate membrane-based motility. The remnants of the nerve endings and/or supporting cells usually covered the cell base. The preservation of the cells was better when enzymatic isolation was omitted. The technique used allowed for high resolution ultrastructural examination of isolated hair cells and, when combined with immunological labeling, may permit the identification of proteins at a molecular level.
    Notes: Zusammenfassung Isolierte Sensorzellen aus dem Innenohr stellen ein akzeptiertes Modell zur Untersuchung von elektrophysiologischen und molekularen Eigenschaften dieser Zellen dar. Um morphologische Substrukturen zu erfassen, haben wir ein rasterelektronenmikroskopisches (REM) Untersuchungsprotokol zur Darstellung der Oberfläche isolierter Haarzellen entwickelt. Die Zellen wurden mechanisch und/oder enzymatisch isoliert und auf mit Alcianblau (0,1–1%) beschichteten Glasplättchen immobilisiert. Es folgte eine chemische Fixation mit Glutardialdehyd und Osmiumtetroxyd. Nach einer Ethanoldehydratation und Trocknung nach der Kritischen-Punkt-Methode mit Hilfe von CO 2 wurden die Proben mit einer dünnen Schicht Gold-Paladium (2–4 nm) beschichtet. Die Untersuchung erfolgte am REM der Fa. Hitachi S-800. Bei optimaler Fixierung wurde die typische zylindrische Form der Zellen erhalten. Wegen der aggressiven Preparation gelang die Darstellung von Tip- und Side-links nur unregelmäßig. Die laterale Zellwand erschien bei maximaler Vergrößerung regelmäßig granuliert bei einer Korngröße von 5–7 nm. Bei der dargestellten Granulation handelt es sich um intramembranöse Partikel (IMP). Diese können Proteinen entsprechen, die durch ihre Fähigkeit zur spannungsabhängigen Konformationsänderung die Motilität der Haarzellen erklären lassen. An der basalen Region der Zelle war keine Granulation feststellbar. Dieser Bereich war mit Nervenendigungen bzw. Resten der Deiters-Zellen bedeckt. Diese Technik ermöglicht die REM-Untersuchung von isolierten Sensorzellen aus dem Innenohr.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s001060050068
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  • 3
    Electronic Resource
    Electronic Resource
    Acute monocytic leukaemia (M5a) in a horse (1996)
    Springer
    Comparative clinical pathology 6 (1996), S. 111-114 
    Details
    ISSN: 1433-2981
    Keywords: Alpha naphthyl acetate esterase ; Cytochemistry ; Horse ; Monocyte ; Monocytic leukaemia ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Acute monocytic leukaemia (M5a) was diagnosed in a 17-year-old Standardbred gelding with lethargy, intermittent pyrexia, oedema of the limbs, harsh lung sounds and submandibular lymphadeopathy. Haematological findings included moderately severe anaemia, thrombocytopenia and a leucocyte count within the reference interval, but characterised by neutropenia and numerous blast cells. Monocytic lineage of the cell population was suggested by examination of Wright-Leishman-stained blood and bone marrow smears. A panel of cytochemical stains disclosed diffuse cytoplasmic α-naphthyl-acetate esterase activity which could be markedly inhibited or abolished in all leukaemic cells by pretreatment with sodium fluoride. In ultrastructural preparations of buffy coat, neoplastic monoblasts had one to two nucleoli, dispersed chromatin, elongated mitochondria, scattered profiles of rough endoplasmic reticulum, bundles of microfilaments and pseudopodia. More differentiated monocytoid cells had infrequent lysosomal granules.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00426052
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  • 4
    Electronic Resource
    Electronic Resource
    Effects of long-term open-air exposure to fluoride, nitrogen compounds and SO2 on visible symptoms, pollutant accumulation and ultrastructure of Scots pine and Norway spruce seedlings (1996)
    Springer
    Trees 10 (1996), S. 157-171 
    Details
    ISSN: 1432-2285
    Keywords: Conifer ; Fluoride ; Nitrogen ; Sulphur dioxide ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract Effects of SO2, aqueous fluoride (NaF) and a solution of nitrogen compounds (NH4NO3) on the visible symptoms, pollutant accumulation and ultrastructure of Scots pine (Pinus sylvestris L.) and Norway spruce [Picea abies (L.) Karst.] seedlings were studied in an open-air experiment lasting for 3 consecutive years. Visible injury symptoms were most pronounced in combination exposures and whenever F was applied. Visible symptoms correlated well with needle pollutant concentrations. Exposure to NaF increased needle F contents particularly when F was applied with SO2 or NH4NO3. This suggests that a reduction in N or SO2 emissions, in F polluted areas, could improve the condition of conifers via decreased accumulation of phytotoxic F in the needles. Norway spruce needles accumulated 2–10 times as much S and F as those of Scots pine. Microscopic observations showed various changes in the needle mesophyll cell ultrastructure. In both species, exposure to SO2 increased significantly the amount of cytoplasmic vacuoles, suggesting detoxification of excess sulphate or low pH. F treatments resulted in a significant enlargement of plastoglobuli in Scots pine and a darkening of plastoglobuli in Norway spruce. All exposures enhanced the accumulation of lipid bodies. An increased portion of translucent plastoglobuli was most pronounced in N treatments. Many of the ultrastructural changes and visible symptoms appeared only as number of years exposed increased, indicating that long-term experiments are needed. Both visible symptoms and ultrastructural changes pointed to the more pronounced sensitivity of Norway spruce compared to Scots pine. Ultrastructural results mostly supported earlier qualitative observations of F, N and SO2 effects on needle mesophyll cell ultrastructure. However, no reduction of thylakoids in SO2 containing exposure or curling of thylakoids in F exposure could be detected in the present study.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02340767
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  • 5
    Electronic Resource
    Electronic Resource
    Ultrastructure of multinucleated giant cell apoptosis in foreign-body granuloma (1996)
    Springer
    Virchows Archiv 428 (1996), S. 165-176 
    Details
    ISSN: 1432-2307
    Keywords: Foreign-body giant cells ; Granulation tissue ; Apoptosis ; Ultrastructure ; p53 expression
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract To elucidate the role of apoptosis in the disappearance of multinucleated giant cells from the granulation tissue in cases of foreign-body granuloma, we induced a foreign-body reaction by implanting a collagen sponge into the dorsum of the rat and observed apoptotic changes within the multinucleated giant cells using electron microscopy. Two types of multinucleated giant cells were identified presenting apoptotic characteristics morphologically. One was characterized by apoptosis of only one nucleus, followed by cytoplasmic changes, rupture of the plasma membrane and necrosis evoking an inflammatory reaction. The other showed typical apoptotic changes in the majority or in all of the nuclei, followed by phagocytosis of the apoptotic syncytia. The results of the present study suggest that apoptosis occurring within only one nucleus might be triggered by overexpression of the p53 protein, because DNA abnormalities are confined to this single nucleus. In contrast apoptosis occurring simultaneously in the majority or all of the nuclei is most probably due to cell death caused by senescence.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00200659
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  • 6
    Electronic Resource
    Electronic Resource
    Fine structural changes of muscle spindles in the gracile axonal dystrophy mutant mouse (1996)
    Springer
    Virchows Archiv 428 (1996), S. 289-296 
    Details
    ISSN: 1432-2307
    Keywords: Mutant mouse ; Axonal degeneration ; Dying back process ; Muscle spindles ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Fine structural changes of muscle spindles in the extensor digitorum longus of the gracile axonal dystrophy mutant mouse were studied from 20 to 120 postnatal days. Degenerative nerve endings in muscle spindles were first recognized at 20 postnatal days. The sensory nerve endings were usually swollen with decrease of cell organelles, and the cytoplasm was electron-lucent. At 50 postnatal days, atrophic nerve endings were frequently observed in the narrow spaces between the indented cell membrane of intrafusal muscle cells and the basement membrane. In addition to degenerative and atrophic changes, regenerative axons showing fine sprouts (with or without Schwann cell projections) appeared in the sensory nerve endings at this time. At 80 postnatal days, sensory nerve endings frequently showed dystrophic changes characterized by axonal dilatation with accumulations of neurofilaments, tubulovesicular structures, mitochondria and myelin-like figures. These findings suggest that axonal transport in the sensory nerve endings is impaired in this mutant mouse. Motor nerve endings were usually well preserved and normal structures even at 80 postnatal days. Intrafusal fibrosis, decrease in number of sensory nerve endings and atrophy of intrafusal muscle fibres were clearly recognized by 100 days of age.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00196703
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  • 7
    Electronic Resource
    Electronic Resource
    Immunocytochemical localization of Tamm-Horsfall protein in the kidneys of normal and nephrolithic rats (1996)
    Springer
    Urological research 24 (1996), S. 201-209 
    Details
    ISSN: 1434-0879
    Keywords: Calcium oxalate ; Hyperoxaluria ; Nephrolithiasis ; Tamm-Horsfall protein ; Immunocytochemistry ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Studies using in vitro systems have indicated that Tamm-Horsfall protein (THP) can interact with calcium oxalate (CaOx) crystals during kidney stone formation. However, information regarding the nature of its participation in this process remains controversial and unclear. In order to better understand the putative interaction of THP and crystals in vivo, we compared the localization of THP in normal rats and in chronic and semi-acute rat models of nephrolithiasis. In these rats, CaOx crystal deposits were induced in the kidneys by administering ethylene glycol (EG) in drinking water. The formation of CaOx mono- and dihydrate aggregates in the urine was confirmed by scanning electron microscopy. Immunohistochemical localization, as well as protein A-gold labeling at the ultrastructural level, demonstrated that in addition to its normal distribution, THP specifically associated with the renal crystal deposits. The THP-containing, organic matrix-like material consisted of a fine, fibrillar meshwork surrounding individual crystals and their aggregates. In addition, THP also appeared in the papilla, where it is normally absent, concurrent with the appearance of crystal deposits in the kidneys. These observations indicate that in nephrolithic rats the normal localization of THP is altered. Such an alteration may indicate an important physiological event related to crystal aggregation and kidney stone formation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00295893
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  • 8
    Electronic Resource
    Electronic Resource
    The microvascular system in ischemic cortical lesions (1996)
    Springer
    Acta neuropathologica 92 (1996), S. 56-63 
    Details
    ISSN: 1432-0533
    Keywords: Key words Brain ; Ultrastructure ; Vascular cast ; Scanning electron microscopy ; Microvasculature
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract In the rat, normal blood flow can be restored in the territory of the occluded artery after an arterial occlusion. This event has been attributed to changes in the collateral vessels supplying the territory of the occluded artery. Since only a limited amount of data is available about the plasticity of the microvascular system after a cortical ischemic lesion, in the present study we have evaluated whether the restoration of blood flow to normal levels in the territory of the middle cerebral artery after permanent ischemia is due only to flow through preexisting collateral vessels or also to the development of new microvessels. Middle cerebral artery occlusion was performed in 45 rats. After 24 h of ischemia, magnetic resonance imaging was used to select 16 rats with cortical lesions of similar size and location. After 2 weeks, vascular corrosion casts were obtained from 8 rats by injection of low-viscosity resin and observed by scanning electron microscopy. A correlative light and electron microscopy study was performed using the remaining 8 rats. Two different patterns of vascular modifications were found, one dorsal and one ventral to the lesion. The dorsal portion of the lesion was vascularized by collateral arteries originating from the anterior or posterior cerebral arteries. Collateral trunks showed a meandering course, mainly in the occipital pole. In the ventral portion of the lesion a complex microvascular system was found characterized by an intense vascular proliferation. The arterioles showed a parallel, candelabrum-like pattern with dichotomic branching. Contraction rings were frequently seen. The capillaries showed a sinusoid-like structure, with a large lumen and a continuous endothelium with many micropinocytotic vesicles. A peripheral ring-shaped venous sinus was composed of a network of flat vessels. These results give the first comprehensive description of the microvascular modifications in a focal model of infarct and suggest that the restoration of blood flow to normal levels described in the territory of the middle cerebral artery after permanent ischemia may be due not only to flow through collateral vessels but also to the development of a new vascular system originating mainly from branches of the middle cerebral artery before the occlusion point.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050489
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  • 9
    Electronic Resource
    Electronic Resource
    Synaptology of the olfactory bulb of an elasmobranch fish, Sphyrna tiburo (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 101-114 
    Details
    ISSN: 1432-0568
    Keywords: Ultrastructure ; Olfaction ; Sharks ; Basal dendrites ; Synapses
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The ultrastructure of the elasmobranch olfactory bulb was examined in order to determine the synaptology of the olfactory circuitry in the bonnethead shark, Sphyrna tiburo. The compartmentalization of the bulb, together with the lack of mitral cell basal dendrites, suggests a different way of performing lateral communication between mitral cells of the olfactory bulb. The results show that granule cells assume an important role by directly interlinking mitral cells. A corollary of this is the segregation of the input onto the mitral cell dendritic arborization: afferent fibers synapse onto the intraglomerular mitral terminals, whereas most local circuit interactions utilize extraglomerular synapses located on the shafts and the somas of the mitral dendrites. Therefore, the elasmobranch synaptic pattern is different from that of higher vertebrates; This might represent the use of a different neural route to achieve the same processing task.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00214701
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  • 10
    Electronic Resource
    Electronic Resource
    Synaptic organization of afferent projections to the supramammillary nucleus of the rat (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 249-257 
    Details
    ISSN: 1432-0568
    Keywords: WGA-HRP ; anterograde tracing ; Ultrastructure ; Preoptic area ; Nucleus of diagonal band ; Laterodorsal tegmental nucleus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We studied the fine structure of afferent terminals from the preoptic area, the nucleus of the diagonal band of Broca, the infralimbic cortex and the laterodorsal tegmental nucleus within the supramammillary nucleus (SUM) using the anterograde tracing method of horse-radish peroxidase conjugated with wheat germ agglutinin (WGA-HRP). Injection of WGA-HRP into the preoptic area permitted ultrastructural recognition of many anterogradely labeled terminals in the SUM. Almost all labeled terminals (99%) contained clear round synaptic vesicles and formed asymmetric synaptic contacts (Gray's type I). About 86% of labeled terminals from the nucleus of the diagonal band were asymmetric (Gray's type I), whereas 14% contained pleomorphic synaptic vesicles and formed symmetric synaptic contacts (Gray's type II). Almost all labeled terminals from the infralimbic cortex were located in the ventral part of the SUM, and 95% of labeled terminals were Gray's type I. The majority of labeled terminals (90%) from the laterodorsal tegmental nucleus were Gray's type I, and the remaining (10%) were Gray's type II. The percentage of labeled terminals with dense-cored vesicles was very high in terminals from the preoptic area (70%), and low in terminals from the infralimbic cortex (19%). Labeled terminals in all cases contacted mainly intermediate-sized dendrites (0.5–1.0 μm diameter). All cases had only a few labeled axosomatic terminals. The cases of injections into the preoptic area and the diagonal band nucleus had some reciprocal connections at the ultrastructural level.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00198328
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  • 11
    Electronic Resource
    Electronic Resource
    Characterization of the interstitial cells associated with the submuscular plexus of the guinea-pig colon (1996)
    Springer
    Anatomy and embryology 194 (1996), S. 49-55 
    Details
    ISSN: 1432-0568
    Keywords: Pacemaker ; Interstitial cells of Cajal ; Intestine ; Ultrastructure ; Immunohistochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Interstitial cells associated with the submuscular plexus of the guinea pig colon were studied by electron microscopy and by light microscopic wholemount stretch preparations. Their cytoplasmic features are similar to those of fibroblasts and they contain a well-developed Golgi apparatus, granular endoplasmic reticulum and many mitochondria. Intermediate filaments are abundantly distributed throughout the perinuclear region and processes. Numerous caveolae, a basal lamina and subsurface cisterns are observed on the cell membrane as in smooth muscle cells. The most characteristic feature of this cell type is the existence of many large gap junctions that interconnect these cells to each other and with the smooth muscle cells. Nerve varicosities containing synaptic vesicles are observed in close apposition with cells of this type. Whole-mount preparations stained by the zinc iodide-osmic acid method and by vimentin immunohistochemistry clearly demonstrated the stellate form of these gap junction-rich cells and suggested that they correspond to the interstitial cells of Cajal.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00196314
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  • 12
    Electronic Resource
    Electronic Resource
    Effects of long-term open-air exposure to fluoride, nitrogen compounds and SO2 on visible symptoms, pollutant accumulation and ultrastructure of Scots pine and Norway spruce seedlings (1996)
    Springer
    Trees 10 (1996), S. 157-171 
    Details
    ISSN: 0931-1890
    Keywords: Key words Conifer ; Fluoride ; Nitrogen ; Sulphur dioxide ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract  Effects of SO2, aqueous fluoride (NaF) and a solution of nitrogen compounds (NH4NO3) on the visible symptoms, pollutant accumulation and ultrastructure of Scots pine (Pinus sylvestris L.) and Norway spruce [Picea abies (L.) Karst.] seedlings were studied in an open-air experiment lasting for 3 consecutive years. Visible injury symptoms were most pronounced in combination exposures and whenever F was applied. Visible symptoms correlated well with needle pollutant concentrations. Exposure to NaF increased needle F contents particularly when F was applied with SO2 or NH4NO3. This suggests that a reduction in N or SO2 emissions, in F polluted areas, could improve the condition of conifers via decreased accumulation of phytotoxic F in the needles. Norway spruce needles accumulated 2 – 10 times as much S and F as those of Scots pine. Microscopic observations showed various changes in the needle mesophyll cell ultrastructure. In both species, exposure to SO2 increased significantly the amount of cytoplasmic vacuoles, suggesting detoxification of excess sulphate or low pH. F treatments resulted in a significant enlargement of plastoglobuli in Scots pine and a darkening of plastoglobuli in Norway spruce. All exposures enhanced the accumulation of lipid bodies. An increased portion of translucent plastoglobuli was most pronounced in N treatments. Many of the ultrastructural changes and visible symptoms appeared only as number of years exposed increased, indicating that long-term experiments are needed. Both visible symptoms and ultrastructural changes pointed to the more pronounced sensitivity of Norway spruce compared to Scots pine. Ultrastructural results mostly supported earlier qualitative observations of F, N and SO2 effects on needle mesophyll cell ultrastructure. However, no reduction of thylakoids in SO2 containing exposure or curling of thylakoids in F exposure could be detected in the present study.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/PL00009644
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  • 13
    Electronic Resource
    Electronic Resource
    Coexistence of paired helical filaments and polyglucosan bodies in the same neuron in an autopsy case of Alzheimer’s disease (1996)
    Springer
    Acta neuropathologica 92 (1996), S. 511-514 
    Details
    ISSN: 1432-0533
    Keywords: Key words Paired helical filament ; Polyglucosan ; body ; Alzheimer’s disease ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The coexistence of polyglucosan bodies (PBs) and paired helical filaments (PHFs) in the same neuron is reported in an autopsy case of Alzheimer’s disease. The patient was a 56-year-old Japanese male with a typical clinical course and pathological findings of Alzheimer’s disease. Electron microscopically, numerous neurofibrillary tangles, mainly composed of PHFs, were observed in the neuronal cytoplasm, axons and dendrites. Some of them coexisted with other filamentous structures, which comprised randomly oriented branching filaments with a diameter of 5–10 nm. These structures were compatible with PBs. Glial tangles could not be found. Coexistence of these two structures was thought to occur in neurites.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050553
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  • 14
    Electronic Resource
    Electronic Resource
    Early ultrastructural changes after brief histotoxic hypoxia in cultured cortical and hippocampal CA1 neurons (1996)
    Springer
    Acta neuropathologica 92 (1996), S. 541-544 
    Details
    ISSN: 1432-0533
    Keywords: Key words Neuronal cultures ; Iodoacetate ; Histotoxic ; hypoxia ; Ribosomes ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Primary cortical and hippocampal neuronal cultures submitted to brief histotoxic hypoxia suffer delayed neuronal death after 24 h [Uto et al. (1995) J Neurochem 64: 2185–2192]. In this study the ultrastructural changes were monitored during the first 6 h following 5-min histotoxic hypoxia induced by exposure to 100 μM iodoacetate. In both cortical and hippocampal CA1 neurons, disaggregation of ribosomes was the earliest sign of histotoxic pathology. Vacuolizations of mitochondria, endoplasmic reticulum and Golgi apparatus, as well as fragmentation and disintegration of neurofilaments followed later. Signs of apoptotic nuclear degeneration were absent. Our observations demonstrate that, similar to that seen in ischemia, disaggregation of ribosomes after brief histotoxic hypoxia is one of the first pathological alterations heralding delayed neuronal death.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050559
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  • 15
    Electronic Resource
    Electronic Resource
    Eosinophilic bodies in the cerebral cortex of Alzheimer’s disease cases (1996)
    Springer
    Acta neuropathologica 92 (1996), S. 555-561 
    Details
    ISSN: 1432-0533
    Keywords: Key words Homogeneous dense body ; Alzheimer’s disease ; Ultrastructure ; Axonal dystrophy ; Eosinophilic body
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The light microscopical, immunohistochemical and ultrastructural aspects of eosinophilic bodies in the cerebral cortex from patients with Alzheimer’s disease (AD) are described, based on a study of 16 cases of AD, 5 elderly non-demented controls and, as disease controls, 5 cases of Pick’s disease, 9 with progressive supranuclear palsy, 5 with Creutzfeldt-Jakob disease and 1 with Binswanger’s disease. At the light microscopy level, the bodies were clearly separated from the surrounding tissues and were mostly round or elliptic with a diameter of 5–30 μm and a central, intensely eosinophilic core. Ultrastructurally, they consisted of a central homogeneous electron-dense body (HDB), and filamentous structures (resembling either neurofilaments or paired helical filaments) or other small organelles in the periphery. Immunohistochemically, some of these bodies exhibited ring-shaped rims which were positive with antibodies against paired helical filaments, tau-2, phosphorylated neurofilaments and ubiquitin. The bodies were widely distributed throughout the cerebral cortex, but were not observed in the white matter. These bodies were thought to be compatible with one type of axonal dystrophy in the gracile nucleus (termed ‘old’ spheroid by Jellinger), and are here referred to as the HDB-type spheroid based on their ultrastructure. In this study HDB-type spheroids were found in high incidence in the AD cases, but only two HDB-type spheroids were seen in one case of Pick’s disease, and none in any of the other cases of neurodegenerative diseases or in the elderly non-demented controls. It seems plausible that the incidence of HDB-type spheroids in the cerebral cortex might be related to a pathological process and not to a physiological ageing phenomenon, and might be characteristic of, but not unique to, AD.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050561
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  • 16
    Electronic Resource
    Electronic Resource
    Early organization of the pituitary gland in Sparus aurata L. (Teleostei) An ultrastructural study (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 441-452 
    Details
    ISSN: 1432-0568
    Keywords: Pituitary gland ; Development ; Ultrastructure ; Sparus aurata (Teleostei)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The cell organization of the pituitary gland and the relationship between neurohypophysis and adenohypophysis in the early developmental stages of the gilthead sea bream, Sparus aurata, were studied by electron microscopy. In newly hatched larvae, the pituitary gland was embedded in the ventral floor of the diencephalon and separated from the hypothalamus by a continuous basal lamina. Elongated mesenchymal cells next to the ventral surface were observed. At this stage, there was no neurohypophysis and the adenohypophysis consisted of undifferentiated endocrine cells with small scarce secretory granules and a few stellate cells, with no distinctive zonation. An incipient neurohypophysis was present in 1-day-old larvae. The first evagination of the neurohypophysis into the adenohypophysis were observed in 2-day-old larvae and developed progressively with age, being deeper in the caudal zone. Two regions in the adenohypophysis, one anterior — the presumptive pars distalis — and one posterior — the presumptive pars intermedia — were found in 2-day-old larvae. Three regions (rostral and proximal pars distalis and pars intermedia) were clearly distinguishable in 4-day-old larvae. The ultrastructural features of the pituitary endocrine cells varied during gland differentiation, with the secretory granules gradually increasing in number and size, accompanying organelle development. Nevertheless, even in the oldest larvae studied (65 days), undifferentiated cells similar to those in the earliest stages were observed. The first blood vessels appeared in the neurohypophysis around 16 days after hatching. During early development, the pituitary gland progressively emerged from the ventral floor of the brain. By 16 days, the principal pattern of the pituitary gland architecture appeared to be established.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00185875
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  • 17
    Electronic Resource
    Electronic Resource
    Synaptic loss in anterior horn neurons in lower motor neuron disease (1996)
    Springer
    Acta neuropathologica 91 (1996), S. 416-421 
    Details
    ISSN: 1432-0533
    Keywords: Key words Motor neuron disease ; Anterior horn ; neuron ; Synapse ; Active zone ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This report concerns an ultrastructural investigation of the synapses of anterior horn neurons in the lumbar spinal cord of four patients with lower motor neuron disease (LMND) who had no upper motor neuron and corticospinal tract involvement. Anterior horn neurons of five normal individuals served as controls. The cell body area and the number of synapses of the normal-appearing neurons of the LMND patients were significantly reduced (P 〈 0.0001). These findings suggest that synaptic changes of anterior horn neurons could be ascribed to the degeneration of lower motor neurons rather than to the influence of upper motor neuron system degeneration. On the other hand, the lengths of individual synapses (P 〈 0.0001) and of their active zones (P 〈 0.05) were significantly increased in the patients. These increases would indicate that synapses on anterior horn neurons of individuals with LMND appear to have the capacity to react to progressive degeneration and loss of other synapses by means of a compensatory response or plasticity that enhances their efficiency.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050444
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  • 18
    Electronic Resource
    Electronic Resource
    Rattan bamboo blind (Japanese sudare)-like profiles of neurofibrillary tangles in Alzheimer’s disease (1996)
    Springer
    Acta neuropathologica 91 (1996), S. 448-450 
    Details
    ISSN: 1432-0533
    Keywords: Key words Neurofibrillary tangles ; Alzheimer’s ; disease ; Ultrastructure ; Rattan bamboo blind-like ; arrangement
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract An unusual ultrastructure for neurofibrillary tangles, which has not been described so far, is presented in a case of Alzheimer’s disease. This profile consists of parallelly arranged paired helical filaments and criss-cross tubular profiles that are arranged at regular interval of 300–500 nm, resembling rattan bamboo blind or Japanese sudare-like profiles. Coexistence of Hirano bodies in the same neuron is infrequently encountered.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050451
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  • 19
    Electronic Resource
    Electronic Resource
    Ultrastructural consequences of radical damage before and after differentiation of neuroblastoma B-104 cells (1996)
    Springer
    Acta neuropathologica 92 (1996), S. 75-89 
    Details
    ISSN: 1432-0533
    Keywords: Key words Radicals ; Neuron ; Ultrastructure ; Differentiation ; Golgi
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract There is abundant evidence that the pathophysiology leading to neuronal death during post-ischemic brain reperfusion involves radical-mediated damage. Although the ultrastructural alterations accompanying brain ischemia and reperfusion are well characterized, little is known about the ultrastructural alterations that are specific to radical damage. This study examines in differentiated and undifferentiated neuroblastoma B-104 cells the viability (by dye exclusion) and ultrastructural consequences of radical damage initiated by 50 μM cumene hydroperoxide (CumOOH). Differentiation was most notably associated with formation of neurites and an extensive cytoskeletal feltwork. CumOOH-induced cell death was increased after differentiation and was blocked by the iron chelator DETAPAC. The ultrastructural characteristics of radical damage here included: (1) plasmalemmal holes that appear to undergo “patching” by well-organized membrane whorls, (2) accumulation of numerous free ribosomes, (3) markedly increased vesicular trafficking about the Golgi accompanied by Golgi transformation from cisternal organization to clusters of vacuoles with numerous fusing vesicles, (4) development of large multi-layered vacuoles that include damage membranes and organelles and appear to undergo extrusion from the cell, and (5) a general loss of cytoplasmic volume. These ultrastructural alterations developed more rapidly and were consistently more advanced in differentiated cells throughout the 6-h time course. In differentiated cells radical damage also induced the disorganization and subsequent loss of the extensive feltwork of cytoskeletal elements. There was little damage to the membranes of the nuclear envelope and mitochondria. Our observations in this system are strikingly similar to ultrastructural alterations in Golgi and ribosomal organization seen in vulnerable neurons during post-ischemic brain reperfusion and suggest that these alterations during reperfusion reflect the consequence of radical-mediated damage.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004010050492
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  • 20
    Electronic Resource
    Electronic Resource
    Tectorial membrane-organ of Corti relationship during cochlear development (1996)
    Springer
    Anatomy and embryology 194 (1996), S. 501-514 
    Details
    ISSN: 1432-0568
    Keywords: Inner ear ; Hair cell ; Stereociliary attachment ; Mouse ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The development of stereociliary attachment to the tectorial membrane was investigated in the mouse cochlea using transmission and scanning electron microscopy. At the 18th gestational day, only the major tectorial membrane can be identified covering the greater epithelial ridge and the inner hair cells in all turns. At the 19th gestational day, the minor tectorial membrane was first seen in the basal turn, over the outer hair cells. During early stages of development, the stereocilia of hair cells were surrounded by a loose fibrillar material underneath the tectorial membrane. After the 10th postnatal day, the outer hair cells' stereocilia were attached to Kimura's (or Hardesty's) membrane, while inner hair cells' stereociliary bundles were attached to the undersurface of the tectorial membrane near the Hensen's stripe. Between the 10th and the 14th postnatal days, the space between the inner hair cells and the first row of outer hair cells widened by virtue of the growth of the heads of pillar cells, and the inner hair cells' stereocilia were displaced towards the Hensen's stripe. After the 14th postnatal day, the inner hair cells' stereociliary bundles detached from the tectorial membrane, while the outer hair cells' stereocilia remained attached to it. The tip-link system, which connects the tips of the stereocilia to the next tallest stereocilia, is present at birth in the outer hair cells. The marginal pillar, that anchored the tectorial membrane to the underlying organ of Corti during development, first appeared on the 6th postnatal day and disappeared on the 14th–15th postnatal day. The present data together with other reports support the idea that although some structures, such as hair cells' stereocilia and innervation, are already formed early during development, the cochlear microarchitecture is not fully developed morphologically and ready to function normally until the end of the second postnatal week in the mouse.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00185996
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  • 21
    Electronic Resource
    Electronic Resource
    Long-term structural alterations to endothelial cells in vein-to-artery grafts: a quantitative electron microscopic study (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 169-173 
    Details
    ISSN: 1432-0568
    Keywords: Endothelium ; Ultrastructure ; Vein graft ; Morphometry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The intracellular structure of endothelium lining vein-to-artery grafts in rats was analysed, using transmission electron microscopy and morphometry, to determine the ultrastructural adaptations of endothelial cells in this altered vascular environment. Autogenous 4-mm sections of iliolumbar veins were inserted microsurgically into the left common iliac arteries of 16 male Wistar rats. At 3, 6, 26 and 52 weeks the cytoplasmic-vesicular, mitochondrial and rough endoplasmic reticular contents of endothelial cells lining the grafts, the opposite iliac arteries and the remaining ilio-lumbar veins were analysed morphometrically. There was a significant increase in the amount of all these cytoplasmic structures in endothelial cells at 3, 6 and 26 weeks; at 52 weeks there was also a significant increase in the volumes of mitochondria and cytoplasmic vesicles, but not in rough endoplasmic reticulum. It was concluded that the ultrastructure of endothelial cells lining these grafts is changed chronically after graft insertion, and we propose that this may be attributable to altered haemodynamic stresses within the graft.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00214707
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  • 22
    Electronic Resource
    Electronic Resource
    Quantitative electromicroscope study of the oculomotor parasympathetic neurons projecting to the ciliary ganglion in cats: comparison of the synaptic (axo-somatic and axo-proximal dendritic) organization of anterior-dorsal and ventral cell groups (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 229-238 
    Details
    ISSN: 1432-0568
    Keywords: Preganglionic neuron ; Oculomotor nerve ; Parasympathetic nervous system ; Synapse ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The synaptic organization of the oculomotor parasympathetic preganglionic neurons (OPNs), labeled retrogradely after a horseradish peroxidase (HRP) injection into the ciliary ganglion, was studied in cats by electron microscopy. We divided the OPNs into two groups, anterior-dorsal (ADG) and ventral (VG) cell groups, based upon physiological studies in cats suggesting that accomodation-related OPNs are predominantly located anterior and dorsal to the somatic nuclei of the oculomotor nuclear complex (i.e., the anteromedian and Edinger Westphal nuclei, and the ventral central gray area), while pupillo-constriction-related OPNs are predominantly located ventral to the somatic nuclei (i.e., the ventral tegmental area). The synaptic organization of these two groups was quantitatively compared, using a nested analysis of variance to determine statistical significance (P〈0.05). Partial reconstructions of the labeled somata and proximal dendrites were made from tracings of electron micrographs of every 2nd section in serial ultrathin sections that included the nucleolus or were adjacent to sections that included the nucleolus. The mean number of boutons of apposition on a reconstructed labeled soma of VG was significantly greater than that of ADG (mean ±SD; ADG, 5.3±3.3; VG, 8.6±3.2). The mean synaptic density on a VG soma was significantly greater than on an ADG soma (mean±SD; ADG, 3.74±2.11 counts/100 (μm2; VG, 6.30±1.99 counts/100 μm2). The mean synaptic covering ratio on a VG soma was significantly greater than on an ADG soma (mean±SD; ADG, 5.21±2.91%; VG, 10.14±3.76%). The mean estimated number of boutons of apposition on a VG soma was significantly greater than on an ADG soma (mean±SD: ADG, 53±36; VG, 100±48). Boutons were classified on the basis of the shape of their synaptic vesicles as S-type (containing spherical clear synaptic vesicles) or P-type (containing both flattened and spherical clear synaptic vesicles). The mean S-type/S+P-type bouton ratio on a VG soma was significantly greater than on an ADG soma (mean±SD; ADG, 0.31±0.20; VG, 0.67±0.18). The differences demonstrated in this study reinforce, morphologically, the assumption of functional localization of OPNs, and further allow us to estimate the relative characteristics of the synaptic organization of accommodation-related OPNs and pupillo-constriction-related OPNs.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00198326
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  • 23
    Electronic Resource
    Electronic Resource
    Ultrastructure of sympathetic axons and their structural relationship with vascular smooth muscle (1996)
    Springer
    Anatomy and embryology 193 (1996), S. 515-531 
    Details
    ISSN: 1432-0568
    Keywords: Sympathetic axons ; Ultrastructure ; Neuromuscular junctions ; Blood vessels
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract This review focuses on the more recent findings of the structure of sympathetic postganglionic axons and the association of their varicose terminals with vascular smooth muscle. These studies have investigated the innervation of a wide range of vessels from different regions of the vasculature in the rat, guinea pig and rabbit and have predominantly used serial sections and computerised three-dimensional reconstructions of entire varicosities. They have shown, contrary to previous studies conducted in the 1960s and 1970s, that sympathetic axon varicosities commonly form structurally specialised neuromuscular junctions with vascular smooth muscle cells of most resistance arteries and some small veins. In addition, they have shown that most axon varicosities innervating small arterioles and small mesenteric veins form neuromuscular junctions, indicating that neurotransmitter is primarily released at such neuromuscular junctions. This review discusses the structure of sympathetic neuromuscular junctions, their development, structural diversity and distribution on vessels from different regions of the vasculature. These more recent structural findings and their possible significance for our understanding of mechanisms involved in neural transmission in blood vessels is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00187924
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  • 24
    Electronic Resource
    Electronic Resource
    Morphology of the keratin filament network in palm and sole skin: evidence for site-dependent features based on stereological analysis (1996)
    Springer
    Archives of dermatological research 288 (1996), S. 55-62 
    Details
    ISSN: 1432-069X
    Keywords: Key words Palmar and plantar skin ; Ultrastructure ; Stereology ; Intermediate filaments ; Keratin
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Ridged or glabrous skin of palms and soles has a specialized function and can be preferentially involved in various disorders of keratinization. To better define the morphological features of ridged skin, we carried out a qualitative and quantitative (stereological) analysis of normal epidermis from the palm and sole of four subjects. Skin from the upper arm was examined for control purposes. The study focused on the appearance and arrangement of the keratin filament network in relation to epidermal differentiation. Whereas palm and sole epidermis was essentially similar both qualitatively and quantitatively, it differed markedly from the epidermis from the arm. The volume density of keratin filaments was significantly higher ( P 〈 0.03) in all subcorneal layers of the palm and sole compared with the arm. The volume density of the keratin filaments increased markedly from the basal to the upper spinous layer of ridged skin and they formed denser aggregates in the upper spinous and granular layers, providing an extensive matrix for the deposition of keratohyalin. The presence of dense keratin aggregates appeared to be a distinct ultrastructural feature of human ridged skin. Such keratin aggregates have not been described in normal skin from other sites, but showed some resemblance to the keratin clumps seen in non-ridged skin of patients with the Dowling-Meara form of epidermolysis bullosa simplex.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004030050023
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  • 25
    Electronic Resource
    Electronic Resource
    Prediction of prognosis by electron microscopic analysis of myeloma cells (1996)
    Springer
    Annals of hematology 73 (1996), S. 169-173 
    Details
    ISSN: 1432-0584
    Keywords: Key words Multiple myeloma ; Ultrastructure ; Prognosis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  Myeloma cells were ultrastructurally analyzed in relation to survival in 54 patients with myeloma who were treated with melphalan-prednisolone or cyclophosphamide-prednisolone. Since previous studies by electron microscope had demonstrated that the degree of nuclear-cytoplasmic asynchrony of myeloma cells was associated with poor prognosis, this study focused on three kinds of nuclear abnormalities and eight kinds of cytoplasmic abnormalities. The patients were classified into three groups according to the presence of these abnormalities. The median survival times of the first group with five or fewer of 11 different kinds of abnormalities, the second group with 6–8 abnormalities, and the third group with nine or more abnormalities were 2353, 531, and 115 days, respectively. Furthermore, this classification by ultrastructural abnormalities corresponded to those by the initial hemoglobin concentrations, platelet counts, and percentages of myeloma cells and plasmablasts in the bone marrow. These findings suggest that ultrastructural analysis of nuclear and cytoplasmic abnormalities, in addition to nuclear maturity, of myeloma cells may provide important information for predicting the prognosis in myeloma patients.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002770050222
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  • 26
    Electronic Resource
    Electronic Resource
    The storage lesion of platelets: ultrastructural and functional aspects (1996)
    Springer
    Annals of hematology 73 (1996), S. 103-112 
    Details
    ISSN: 1432-0584
    Keywords: Key words Platelet concentrates ; Storage ; Ultrastructure ; α-granules ; Open canalicular system
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  When prepared and stored as concentrates, platelets undergo a lot of structural, biochemical and functional alterations that lead to an impaired function after transfusion. Besides signs of activation like disc-to-sphere transformation, extension of pseudopodes and loss of storage granules, platelets may display a swollen open canalicular system and changes in the structure of their α-granules. These partly reversible morphological alterations correspond to a deterioration of basic metabolic parameters and a decrease in the reactivity of stored platelets to weak agonists. All these changes occur to a very different degree depending on the methods of preparation and storage. With the introduction of acetate-containing additive solutions, the storage conditions could be greatly improved, and platelets from pooled buffy coats and stored in an acetate-containing medium with at least 20% autologous plasma show the best structural integrity over 8 days of storage.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002770050210
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  • 27
    Electronic Resource
    Electronic Resource
    Visualization of crystal-matrix structure. In situ demineralization of mineralized turkey leg tendon and bone (1996)
    Springer
    Calcified tissue international 59 (1996), S. 474-479 
    Details
    ISSN: 1432-0827
    Keywords: Bone ; Apatite ; Collagen ; Demineralization ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine , Physics
    Notes: Abstract A technique to correlate the ultrastructural distribution of mineral with its organic material in identical sections of mineralized turkey leg tendon (MTLT) and human bone was developed. Osmium or ethanol fixed tissues were processed for transmission electron microscopy (TEM). The mineralized tissues were photographed at high, intermediate, and low magnifications, making note of section features such as fibril geometry, colloidal gold distribution, or section artifacts for subsequent specimen realignment after demineralization. The specimen holder was removed from the microscope, the tissue section demineralized in situ with a drop of 1 N HCl, then stained with 2% aqueous vanadyl sulfate. The specimen holder was reinserted into the microscope, realigned with the aid of the section features previously noted, and rephotographed at identical magnification used for the mineralized sections. A one to one correspondence was apparent between the mineral and its demineralized crystal “ghost” in both MTLT and bone. The fine structural periodic banding seen in unmineralized collagen was not observed in areas that were fully mineralized before demineralization, indicating that the axial arrangement of the collagen molecules is altered significantly during mineralization. Regions that had contained extrafibrillar crystallites stained more intensely than the intrafibrillar regions, indicating that the noncollagenous material surrounded the collagen fibrils. The methodology described here may have utility in determining the spatial distribution of the noncollagenous proteins in bone.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00369213
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  • 28
    Electronic Resource
    Electronic Resource
    Electron-microscopic study of dopaminergic structures in the medial subdivision of the monkey nucleus accumbens (1996)
    Springer
    Experimental brain research 111 (1996), S. 41-50 
    Details
    ISSN: 1432-1106
    Keywords: Immunocytochemistry ; Dopamine ; Nucleus accumbens ; Ultrastructure ; Monkey
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The medial subdivision of the monkey nucleus accumbens (NAC) is rich in dopamine (DA) and peptides. In the present investigation the mode of DA transmission in the medial subdivision was studied morphologically by light- and electron-microscopic immunocytochemistry using a monoclonal antibody raised against dopamine. The medial subdivision showed extremely dense accumulation of thick DA-immunoreactive varicose fibers. Electron-microscopic observation of single sections revealed that DA afferents had a relatively high incidence (33.2%) of asymmetric junctions in this area. Approximately 50% of the targets were dendritic shafts, 44.2% dendritic spines, and 5.1% somata. Some DA axons showed terminal profiles en passant within the synaptic complex, some of which showed synaptic triads. The unique ultrastructural features of DA terminals in the medial NAC indicate the existence of specific styles of DA transmission in the limbic structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00229554
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  • 29
    Electronic Resource
    Electronic Resource
    Tacrolimus (FK 506) biotransformation in primary rat hepatocytes depends on extracellular matrix geometry (1996)
    Springer
    Naunyn-Schmiedeberg's archives of pharmacology 353 (1996), S. 461-473 
    Details
    ISSN: 1432-1912
    Keywords: Hepatocytes ; Sandwich culture ; Ultrastructure ; Morphology ; Sirolimus ; Tacrolimus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Established in vitro models for studies of hepatic drug biotransformation include the use of primary hepatocytes. In normal liver the space of Disse provides the possibility of bilateral attachment to extracellular matrix for each hepatocyte. This configuration is disrupted by the cell isolation procedure of normal liver tissue, which delivers suspensions of round shaped cells. In standard culture configurations this unphysiologic cell shape terminates in a morphological dedifferentiation and inability to biotransform drugs. This study analyses the relevance of extracellular matrix geometry in hepatocyte monolayer configurations for expression and activity of cytochrome P450 3A. This enzyme is involved in the biotransformation of a large number of pharmaceuticals including the immunosuppressants tacrolimus and sirolimus. Morphological analysis of primary rat hepatocytes cultured with and without overlay of collagen type I was performed by transmission and scanning electron microscopy. Expression and activity of cytochrome P450 3A was studied by Western blot and the use of two model drugs specific for this enzyme. To this purpose the immunosuppressive drugs tacrolimus and sirolimus were used. Metabolites were analyzed by HPLC and HPLGMS. Two sided attachment to extracellular matrix induces profound changes of the hepatocellular morphology in vitro resulting in the reconstitution of a polyhedric cell shape. This phenomenon is paralleled by an enhanced expression of cytochrome P450 3A and corresponding metabolic activity. As shown for tacrolimus biotransformation, the model may be useful to study complex metabolic patterns. In addition this model may facilitate studies of the kinetics of hepatocellular drug biotransformation in a setting with prolonged stability.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00261444
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  • 30
    Electronic Resource
    Electronic Resource
    Tacrolimus (FK 506) biotransformation in primary rat hepatocytes depends on extracellular matrix geometry (1996)
    Springer
    Naunyn-Schmiedeberg's archives of pharmacology 353 (1996), S. 461-473 
    Details
    ISSN: 1432-1912
    Keywords: Key words Hepatocytes ; Sandwich culture ; Ultrastructure ; Morphology ; Sirolimus ; Tacrolimus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Established in vitro models for studies of hepatic drug biotransformation include the use of primary hepatocytes. In normal liver the space of Disse provides the possibility of bilateral attachment to extracellular matrix for each hepatocyte. This configuration is disrupted by the cell isolation procedure of normal liver tissue, which delivers suspensions of round shaped cells. In standard culture configurations this unphysiologic cell shape terminates in a morphological dedifferentiation and inability to biotransform drugs. This study analyses the relevance of extracellular matrix geometry in hepatocyte monolayer configurations for expression and activity of cytochrome P450 3A. This enzyme is involved in the biotransformation of a large number of pharmaceuticals including the immunosuppressants tacrolimus and sirolimus. Morphological analysis of primary rat hepatocytes cultured with and without overlay of collagen type I was performed by transmission and scanning electron microscopy. Expression and activity of cytochrome P450 3A was studied by Western blot and the use of two model drugs specific for this enzyme. To this purpose the immunosuppressive drugs tacrolimus and sirolimus were used. Metabolites were analyzed by HPLC and HPLC/MS. Two sided attachment to extracellular matrix induces profound changes of the hepatocellular morphology in vitro resulting in the reconstitution of a polyhedric cell shape. This phenomenon is paralleled by an enhanced expression of cytochrome P450 3A and corresponding metabolic activity. As shown for tacrolimus biotransformation, the model may be useful to study complex metabolic patterns. In addition this model may facilitate studies of the kinetics of hepatocellular drug biotransformation in a setting with prolonged stability.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00261444
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  • 31
    Electronic Resource
    Electronic Resource
    Quantitative analysis of ultrastructural changes during zygotic and somatic embryogenesis in pearl millet (Pennisetum glaucum [L.] R. Br.) (1996)
    Springer
    Sexual plant reproduction 9 (1996), S. 286-298 
    Details
    ISSN: 1432-2145
    Keywords: Somatic embryogenesis ; Ultrastructure ; Pennisetum ; Poaceae ; Morphometrics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Ultrastructural changes during zygotic and somatic embryogenesis in pearl millet (Pennisetum glaucum [L.] R. Br.) were quantified using morphometric techniques. The total area per cell profile and the cell volume percentage of the whole cell, endoplasmic reticulum (ER), Golgi bodies, mitochondria, nuclei, lipids, plastids, starch grains and vacuoles were measured and comparisons made between three zygotic and three somatic embryo developmental stages. All measurements were taken from scutellar or scutellar-derived cells. Zygotic embryogenesis was characterized by increases in cell size, lipids, plastids, starch, Golgi bodies, mitochondria and ER. Somatic embryogenesis was characterized by two phases of cell development: (1) the dedifferentiation of scutellar cells involving a reduction in cell and vacuole size and an increase in cell activity during somatic proembryoid formation and (2) the development of somatic embryos in which most cell organelle quantities returned to values found in late coleoptile or mature predesiccation zygotic stages. In summary, although their developmental pathways differed, the scutella of somatic embryos displayed cellular variations which were within the ranges observed for later stages of zygotic embryogenesis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02152704
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  • 32
    Electronic Resource
    Electronic Resource
    Quantitative analysis of ultrastructural changes during zygotic and somatic embryogenesis in pearl millet (Pennisetum glaucum [L.] R. Br.) (1996)
    Springer
    Sexual plant reproduction 9 (1996), S. 286-298 
    Details
    ISSN: 1432-2145
    Keywords: Key words Somatic embryogenesis ; Ultrastructure ; Pennisetum ; Poaceae ; Morphometrics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract  Ultrastructural changes during zygotic and somatic embryogenesis in pearl millet (Pennisetum glaucum [L.] R. Br.) were quantified using morphometric techniques. The total area per cell profile and the cell volume percentage of the whole cell, endoplasmic reticulum (ER), Golgi bodies, mitochondria, nuclei, lipids, plastids, starch grains and vacuoles were measured and comparisons made between three zygotic and three somatic embryo developmental stages. All measurements were taken from scutellar or scutellar-derived cells. Zygotic embryogenesis was characterized by increases in cell size, lipids, plastids, starch, Golgi bodies, mitochondria and ER. Somatic embryogenesis was characterized by two phases of cell development: (1) the dedifferentiation of scutellar cells involving a reduction in cell and vacuole size and an increase in cell activity during somatic proembryoid formation and (2) the development of somatic embryos in which most cell organelle quantities returned to values found in late coleoptile or mature predesiccation zygotic stages. In summary, although their developmental pathways differed, the scutella of somatic embryos displayed cellular variations which were within the ranges observed for later stages of zygotic embryogenesis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004970050045
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  • 33
    Electronic Resource
    Electronic Resource
    Development and cellular organization ofPinus sylvesfris pollen tubes (1996)
    Springer
    Sexual plant reproduction 9 (1996), S. 93-101 
    Details
    ISSN: 1432-2145
    Keywords: Cytoskeleton ; Microscopy ; Pinus sylvestris ; Pollen ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The organization ofPinus sylvestris pollen tubes during growth was studied by video microscopy of living cells and by electron microscopy after freeze-fixation and freeze-substitution (FF-FS). Pollen germinated and the tubes grew slowly for a total period of about 7 days. Some of the grains formed two tubes, while 10–50% of the tubes ramified. These features are in accordance with development in vivo. The cytoplasmic hyaline cap at the tip disappeared during the 2nd or 3rd day of culture. Aggregates of starch grains progressively migrated from the grain into the tube and later into the branches. Vacuoles first appeared at day 2 and eventually filled large parts of the tube. The tube nucleus was located at variable distances from the tip. Some of the organelles showed linear movements in a mostly circulatory pattern, but the majority of the organelles showed brownian-like movements. Rhodamine-phalloidin-stained actin filaments had a gross axial orientation and were found throughout the tube including at the tip. The ultrastructure of pollen tubes was well preserved after FF-FS, but signs of shrinkage were visible. The secretory vesicles in growing tips were not organized in a vesicle cone, and coated pits had a low density with only local accumulations, which is in accordance with slow growth. The mitochondria contained small cristae and a darkly stained matrix and were located more towards the periphery of the tube, indicating low respiratory activity and low oxygen levels. The dictyosomes carried typical trans-Golgi networks, but some contained less than the normal number of cisternae. Other elements of the cytoplasm were irregularly spaced rough endoplasmic reticulum, many multivesicular bodies, lipid droplets and two types of vacuoles. The typical organization associated with tip growth in angiosperm pollen tubes, e.g.Nicotiana tabacum, was not present inP. sylvestris pollen tubes. The different morphology may relate to the growth rate and not to the type of growth.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02153056
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    Electronic Resource
    Electronic Resource
    Development and cellular organization of Pinus sylvestris pollen tubes (1996)
    Springer
    Sexual plant reproduction 9 (1996), S. 93-101 
    Details
    ISSN: 1432-2145
    Keywords: Key words Cytoskeleton ; Microscopy ; Pinus sylvestris ; Pollen ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract  The organization of Pinus sylvestris pollen tubes during growth was studied by video microscopy of living cells and by electron microscopy after freeze-fixation and freeze-substitution (FF-FS). Pollen germinated and the tubes grew slowly for a total period of about 7 days. Some of the grains formed two tubes, while 10–50% of the tubes ramified. These features are in accordance with development in vivo. The cytoplasmic hyaline cap at the tip disappeared during the 2nd or 3rd day of culture. Aggregates of starch grains progressively migrated from the grain into the tube and later into the branches. Vacuoles first appeared at day 2 and eventually filled large parts of the tube. The tube nucleus was located at variable distances from the tip. Some of the organelles showed linear movements in a mostly circulatory pattern, but the majority of the organelles showed brownian-like movements. Rhodamine-phalloidin-stained actin filaments had a gross axial orientation and were found throughout the tube including at the tip. The ultrastructure of pollen tubes was well preserved after FF-FS, but signs of shrinkage were visible. The secretory vesicles in growing tips were not organized in a vesicle cone, and coated pits had a low density with only local accumulations, which is in accordance with slow growth. The mitochondria contained small cristae and a darkly stained matrix and were located more towards the periphery of the tube, indicating low respiratory activity and low oxygen levels. The dictyosomes carried typical trans-Golgi networks, but some contained less than the normal number of cisternae. Other elements of the cytoplasm were irregularly spaced rough endoplasmic reticulum, many multivesicular bodies, lipid droplets and two types of vacuoles. The typical organization associated with tip growth in angiosperm pollen tubes, e.g. Nicotiana tabacum, was not present in P. sylvestris pollen tubes. The different morphology may relate to the growth rate and not to the type of growth.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004970050015
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    Electronic Resource
    Electronic Resource
    Reevaluation of synaptic relationships of cerebellar terminals in the ventral lateral nucleus of the rhesus monkey thalamus based on serial section analysis and three-dimensional reconstruction (1996)
    Springer
    Experimental brain research 109 (1996), S. 219-239 
    Details
    ISSN: 1432-1106
    Keywords: Cerebellothalamic projection ; Neuronal circuits ; Ultrastructure ; Synapse ; Monkey
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Terminals of cerebellar afferents (CB) to different regions of the ventral lateral nucleus (VL) of the rhesus monkey thalamus were labeled with wheat germ agglutinin-horseradish peroxidase following injections into the dentate nucleus. Synaptic relationships of 17 CB with projection neuron dendrites (PNd) and local circuit neuron dendrites (LCNd) were analyzed in serial ultrathin sections from dorsal and ventral VL regions, which are known to differ cytoarchitecturally and functionally. Three terminals were reconstructed using three-dimensional (3D) computer image analysis techniques to obtain volumetric and planar measurements. CB in the ventral VL were often flat and elongated with synaptic vesicles arranged in clusters. Each CB was engaged with one PNd and one to four LCNd. A single bouton formed 8–50 synaptic contacts, with those on PNd outnumbering the ones on LCNd 4.1∶1. Only some CB in the ventral VL were engaged in complex synaptic arrangements such as triads and serial synapses. Most CB in the dorsal VL displayed a roundish shape and numerous uniformly distributed synaptic vesicles. They formed 5–25 synaptic contacts with a 3∶1 ratio of contacts on PNd compared with those on LCNd. CB in the dorsal VL participated in a variety of complex synaptic arrangements. Two types of triads were found: classic with CB, PNd and LCNd, and unconventional with CB and two LCNd. CB were also involved in serial synapses with two LCNd or LCNd and another PNd, and serial sequential synapses with two LCNd and a PNd. Three glomerulus-like structures were encountered in the dorsal VL. 3D reconstruction and volumetric measurements revealed that synaptic contacts formed by CB on PNd had varying shapes and sizes (0.022–0.274 μm2). Synapses formed on LCNd were larger (0.09–0.407 μm2). The total area of all active zones of a single CB on LCNd was either equal to or about 40% smaller than that of synapses on PNd. The entire active zone area comprised 1–1.6% of the total CB surface area and did not seem to correlate with the volume. Synaptic contacts formed by associated LCNd on PNd in complex arrangements were usually small (0.021–0.044 μm2). The results suggest that: synapses formed by CB on PNd and LCNd, and synapses formed by LCNd on PNd may differ in strength; a variety of different circuits participate in the processing of cerebellar afferent information in the primate VL; and these circuits differ in functionally different VL subdivisions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00231783
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    Electronic Resource
    Electronic Resource
    Synaptic organization of damaged infraorbital nerve axons in perinatal rats: demonstration by galanin immunocytochemistry (1996)
    Springer
    Experimental brain research 110 (1996), S. 47-54 
    Details
    ISSN: 1432-1106
    Keywords: Trigeminal nerve ; Primary afferents ; Synapses ; Ultrastructure ; Vibrissae ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Neonatal transection of the infraorbital nerve (ION; the trigeminal, V, branch that supplies the mystacial vibrissae follicles) results in an upregulation of galanin in the central arbors of primary afferent axons. The present study was undertaken to evaluate the synaptic organization of these galanin-positive primary afferents and compare it with that of normal neurobiotin/biocytin-labeled primary afferent axons from animals of the same age. Examination of 1200 neurobiotin/biocytin-labeled profiles in V nucleus principalis (PrV) of rats killed on postnatal day (P-) 7 indicated that 23.3% (n=279) of these profiles made synaptic contacts: 87.4% were axodendritic, 8.9% were axoaxonic, 2.8% were axosomatic, and 0.7% were axospinous. Evaluation of 1200 galanin-positive profiles in PrV from rats that sustained transection of the ION on P-0 and were killed on P-7 indicated that only 64 (5.3%) of these profiles made synaptic contacts (P〈0.05 compared with the intact animals). Of the galanin-positive profiles that did make synapses in PrV, 81.2% (n=52) were axodendritic and 18.8% (n=12) were axoaxonic. These results indicate that galanin released by damaged ION primary afferents in PrV is likely to affect the activity of second-order V neurons by a paracrine action rather than by acting at specific synapses.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00241373
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    Electronic Resource
    Epithelioid angiosarcoma of the thyroid (1996)
    Springer
    Virchows Archiv 429 (1996), S. 131-137 
    Details
    ISSN: 1432-2307
    Keywords: Thyroid ; Angiosarcoma ; Immunohistochemistry ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Epithelioid angiosarcomas of the thyroid usually develop in people living in Alpine regions, and only rare cases arising in subjects living in nonmountainous areas have been reported. We describe the clinicopathological features of a series of seven cases collected from non-Alpine areas. All patients were adults. The tumours appeared as haemorrhagic, unencapsulated, sometimes cystic nodules. In two cases multinodularity was present. They were composed of large, epithelioid cells, which lined vascular-like spaces or were arranged in solid sheets. Intracytoplasmic lumina containing red blood cells were identified. Neoplastic cells were diffusely positive for factor VIII-related antigen, Ulex europaeus agglutinin, CD31 and keratin peptides. Ultrastructural studies were performed in four cases and showed features of endothelial differentiation. An average follow-up of 3.8 years disclosed that four patients died of disease after a median survival time of 5 months, whereas 3 patients are still alive with no evidence or residual disease 27, 32 and 66 months after thyroidectomy. The good prognosis in these patients appears to be related mainly to the absence of extraglandular tumour spread at the time of surgery.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00192435
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  • 38
    Electronic Resource
    Electronic Resource
    Effect of α-fluoromethylhistidine-evoked histamine depletion on ultrastructure of endocrine cells in acid-producing mucosa of stomach in mouse, rat and hamster (1996)
    Springer
    Cell & tissue research 286 (1996), S. 375-384 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Endocrine cells ; Stomach-ECL cells ; Ultrastructure ; Histamine ; α-Fluoromethylhistidine ; Secretory vesicles ; Rat (Sprague Dawley) ; Mouse (NMRI) ; Hamster (Syrian)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. The oxyntic mucosa of the mammalian stomach is rich in endocrine cells, such as ECL cells, A-like cells, somatostatin cells, D1/P cells and, in some species, enterochromaffin cells. The various endocrine cell types can be distinguished on the basis of their characteristic cytoplasmic granules and vesicles. The ECL cells contain numerous large secretory vesicles and relatively few, small electron-dense granules and small clear microvesicles. We have suggested that in the rat the ECL cells contain most of the gastric histamine with the secretory vesicles as the major histamine storage site in these cells. α-Fluoromethylhistidine is an irreversible inhibitor of histidine decarboxylase, the histamine-forming enzyme. We have previously shown that this enzyme inhibitor depletes histamine from the ECL cells in the rat and reduces the number of secretory vesicles in the cytoplasm. In the present study, we have examined whether α-fluoromethylhistidine affects the ECL cells in other species and whether it affects other types of endocrine cells in the oxyntic mucosa of the rat. Mice, rats and hamsters were treated with the inhibitor (3 mg/kg per h) via minipumps subcutaneously for 24 h. This treatment lowered the oxyntic mucosal histamine concentration by 65–90% and the number and volume density of the secretory vesicles by 85–95% in the ECL cells of the three species examined. In contrast, the number and volume density of granules and microvesicles were not greatly affected. No evidence was found for an effect of α-fluoromethylhistidine on A-like cells, somatostatin cells or D1/P cells of the rat stomach, suggesting that, unlike the ECL cells, they do not contain histamine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050707
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    Electronic Resource
    Electronic Resource
    Immunohistochemical demonstration of nerve growth factor receptor in bovine testis (1996)
    Springer
    Cell & tissue research 285 (1996), S. 189-197 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Testis ; Nerve growth factor receptor ; Immunohistochemistry ; Ultrastructure ; Bovine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. Nerve growth factor receptor (low-affinity form) was demonstrated immunohistochemically in bovine testis by using a monoclonal mouse anti-human antibody. In the 7-month-old fetus and in the early postnatal testis, the peritubular and intertubular fibroblast-like mesenchymal cells showed a strong reaction. Following differentiation of these cells into Leydig and myoid peritubular cells, the nerve growth factor receptor was no longer expressed. However, peritubular and intertubular testicular fibroblasts/fibrocytes, which are also derived from mesenchymal precursors, remained positive. Additionally, the nerve growth factor receptor was demonstrated in postnatal prespermatogonia, A-spermatogonia, I-spermatogonia and members of the spermatogonia precursor cell line; B-spermatogonia remained negative. In A-spermatogonia and I-spermatogonia, the expression of the nerve growth factor receptor was cell-cycle-dependent and was mostly observed during G1-phase. Pre-embedding ultrahistochemistry with gold-conjugated antibody followed by silver-enhancement revealed that the nerve growth factor receptor was localized at the outer cell surface. The metal granules showed a regular distribution in positive spermatogonia. In testicular fibroblasts/fibrocytes the long narrow processes were preferentially decorated.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050636
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  • 40
    Electronic Resource
    Electronic Resource
    Time course of hypertrophic and ultrastructural responses of rat stomach enterochromaffin-like cells to sustained hypergastrinemia (1996)
    Springer
    Cell & tissue research 284 (1996), S. 55-63 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Enterochromaffin-like (ECL) cells ; Gastrin ; Granules/vesicles ; Hypertrophy ; Ultrastructure ; Rat (Sprague Dawley)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. Previously, we have investigated the effects of short-term (minutes to hours) and long-term (weeks to months) stimulation with gastrin on the histamine-producing enterochromaffin-like (ECL) cells in the oxyntic mucosa of rat stomach. The present study examines the response of the ECL cells of freely fed rats to sustained hypergastrinemia over a time span of a few hours to four weeks. Sustained hypergastrinemia was induced by the continuous subcutaneous infusion of human Leu15-gastrin-17. The histidine decarboxylase (HDC) activity and histamine concentration in the oxyntic mucosa were monitored throughout the study. ECL cell profiles in electron micrographs were analysed planimetrically. The HDC activity displayed a 4-fold increase within the first two days. Subsequently, it remained at a plateau. The histamine concentration increased 2- to 3-fold in response to gastrin. The rise in histamine was slower than the rise in HDC activity. At no time point was there a reduced concentration of histamine. The ECL cells increased in size after 4 days of hypergastrinemia, reaching a maximum cell profile area after 2 weeks and remaining enlarged for the duration of the study. The secretory vesicles were reduced in number after 1 day, returning gradually to the pre-stimulation value thereafter; their volume density remained reduced during the 6-day observation period. Vacuoles started to appear after 1 day of hypergastrinemia and their number and volume density increased, reaching a maximum after 4 days. The number and volume density of the microvesicles increased and plateaued after 2 days of hypergastrinemia. The number of granules per cell profile was unaffected but their volume density was greatly reduced after 4 days of hypergastrinemia (reflecting the ECL cell hypertrophy). The present findings establish the time course of activation of the ECL cells in response to sustained hypergastrinemia over a time span of a few hours to four weeks; a new ”steady state” situation at a high level of activity has been established after about a week.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050566
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    Electronic Resource
    Electronic Resource
    Phagocytosis of lectin-opsonized fungal cells and endocytosis of the ligand by insect Spodoptera exigua granular hemocytes: an ultrastructural and immunocytochemical study (1996)
    Springer
    Cell & tissue research 285 (1996), S. 57-67 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Phagocytosis ; Insect hemocytes ; Lectins ; Fungal entomopathogens ; Ultrastructure ; Immunocytochemistry ; Cytoskeleton ; Spodoptera exigua (Insecta) ; Paecilomyces farinosus (Fungi-Deuteromycotina)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. Phagocytosis of blastospores of the fungal entomopathogen Paecilomyces farinosus by granular hemocytes from larvae of Spodoptera exigua (beet armyworm) was studied. Blastospores were opsonized with a galactose-specific lectin purified from S. exigua hemolymph or with peanut agglutinin prior to incubation with hemocytes. Observations of thin sections revealed that pseudopodia extending from granulocytes attached to ligands (lectins, lectin conjugates) on the blastospores, and that the ligands became detached from the fungal surfaces and were endocytosed by granulocytes via coated pits on the plasma membrane. Coated vesicles bearing the endocytosed molecules appeared to be transported to the hemocytic granules. In other cases, ligand still coated the blastospores after phagocytosis and may have later concentrated within the phagosome along with digested fungal cell wall components. Phagocytosis of blastospores and clustering of a biotinylated lectin conjugate on or within the granulocytes were inhibited by drugs targeting cytoskeletal elements. Actin was concentrated in the pseudopodia of phagocytic granulocytes and may be directly associated with lectin receptor(s). Microtubules were abundant in the granulocytes, sometimes in specific regions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050620
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    Electronic Resource
    Electronic Resource
    Mineralization during matrix-vesicle-mediated mantle dentine formation in molars of albino rats: a microanalytical and ultrastructural study (1996)
    Springer
    Cell & tissue research 284 (1996), S. 223-230 
    Details
    ISSN: 1432-0878
    Keywords: Key words: Mineralization ; Matrix vesicles ; Dentine ; Ultrastructure ; Element analysis ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Abstract. The purpose of this study was to elucidate the mineralization process of mantle dentine by ultrastructural and element-analytical investigation of matrix vesicles and successive stages. Upper second molars of albino rats were cryofixed and embedded in resin after freeze drying. Semithin dry sections were prepared for analyzing the calcium and phosphorus concentrations in the mineralized matrix vesicles or noduli, larger mineralized islands, and the mantle dentine. For ultrastructural studies, it was necessary to reduce section contact with hydrous fluids to a minimum in order to avoid preparation artifacts. The first mineral deposits were recognized as dot-like formations both in the interior of matrix vesicles and in association with the inner vesicle membrane. This indicated the existence of mineral nucleating sites located both at the inner membrane and at calcium-phosphate-binding macromolecules in the interior of the matrix vesicles. A significantly higher mineral content was found in mineralized matrix vesicles than in the mineralized extravesicular regions of the mineralized islands, suggesting the existence of a rapidly and densely mineralizing matrix in the matrix vesicles. A significant increase in mineral content per volume proceeding from the mineralized islands to mantle dentine suggested a further increase in the density of mineral.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004410050582
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    Electronic Resource
    Electronic Resource
    Morphological changes in the central vacuole ofBlastocystis hominis during in vitro culture (1996)
    Springer
    Protoplasma 194 (1996), S. 63-68 
    Details
    ISSN: 1615-6102
    Keywords: Blastocystis hominis ; Central vacuole ; In vitro culture ; Accumulation ; Carbohydrates ; Lipids ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Morphological changes in the central vacuole during the growth in in vitro culture ofBlastocystis hominis were investigated by light and electron microscopy. Most cells in log phase and an early stationary phase showed a positive staining reaction in the central vacuole with PAS or Sudan black B stain, whereas cells in late stationary phase showed few positive reactions. Electron microscopic observations revealed that 95% ofB. hominis cells in log phase and 50% of cells in early stationary phase, had a substantial accumulation of electron-dense material in the central vacuole. In contrast, only 25% of the organisms in late stationary phase had an electron-dense central vacuole, while more than 50% of cells had an electron-lucent central vacuole. These results indicate thatB. hominis accumulated carbohydrates and lipids in the central vacuole during cell growth and that the organism probably consumed these metabolic substances during stationary growth. Therefore, it is strongly suggested that the central vacuole is an important organelle for storage of metabolic substances, such as carbohydrates and lipids, required for cell growth.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01273168
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    Electronic Resource
    Endoplasmic reticulum derived decorated tubules in the sieve elements ofNymphaea (1996)
    Springer
    Protoplasma 193 (1996), S. 213-221 
    Details
    ISSN: 1615-6102
    Keywords: Decorated tubules ; Endoplasmic reticulum ; Nymphaea ; Sieve elements ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Bundles of decorated tubules found in the sieve elements ofNymphaea have been studied with the transmission electron microscope. Comparatively straight tubules (100 nm in diameter) arise from the endoplasmic reticulum during early stages of sieveelement development and subsequently associate into bundles of up to 100 tubules that parallel the longitudinal cell axis. From the start of their formation the tubules are structurally distinct from other ER profiles due to their dense decoration with particles. High magnifications reveal an orderly array of the particles (about 24 surround a 100 nm tubule) and suggest a modification of their membrane so that it is no longer dissolvable into a regular three-layered structure. Later during sieve-element ontogeny the decorated tubules get invaginated by smooth ER membranes, thereby squeezing out the intratubular (extracytoplasmic) space. As a result a double mantle is formed that surrounds a plasmatic cylinder. Decorated 100 nm tubules with inner membranes are present in enucleate mature sieve elements ofNymphaea alba andN. tuberosa. Considerably larger tubules (about 200 nm in diameter) were found inN. Candida andN. tetragona and occasionally also inNuphar and Barclaya, two other genera from the same family. The decoration of the tubules and their subsequent invagination by smooth membranes are discussed with respect to the controlled autolysis of sieve elements.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01276647
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    Electronic Resource
    Electronic Resource
    Plastid biogenesis in embryonic pea leaf cells during early germination (1996)
    Springer
    Protoplasma 195 (1996), S. 59-67 
    Details
    ISSN: 1615-6102
    Keywords: Endoplasmic reticulum ; Germination ; Lipid bodies ; Pisum sativum ; Plastid biogenesis ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The ultrastructure of embryonic pea leaf cells was examined during the first 24 h of imbibition of dry seeds. Special attention was paid to plastids, which underwent two interesting interactions during this period. The first was a close physical association between the endoplasmic reticulum and plastids. The second was an association of numerous lipid bodies with the surface of plastids. The functional implications of these associations are considered.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01279186
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  • 46
    Electronic Resource
    Electronic Resource
    The ultrastructure of hemocytes inDactylopius confusus (Cockerell), and the role of granulocytes in the synthesis of cochineal dye (1996)
    Springer
    Protoplasma 192 (1996), S. 199-216 
    Details
    ISSN: 1615-6102
    Keywords: Scale insect ; Cochineal scale ; Hemocytes ; Coccid ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The ultrastructural study of free circulating hemocytes in the adult cochineal scale,Dactylopius confusus (Cockerell), demonstrated five cell types: prohemocytes, typical granulocytes (T-granulocytes), oenocytoids, plasmatocytes, and granulocytes with modified sub-cellular structure to perform a special synthetic and secretory function, which we refer to as “modified granulocytes” (M-granulocytes). Prohemocytes showed undifferentiated sub-cellular structure of the basic stem cell type (i.e., high cytoplasmic density with numerous ribosomes, centrally located large nucleus with a distinct nucleolus, and poorly developed endoplasmic reticulum). The commonly observed typical granulocytes (T-granulocytes) had several smooth endoplasmic reticulum (SER) with dilated cisternae and many SER-derived membrane bounded granules of different sizes and electron density. Oenocytoids were identified by the presence of many crystals, RER-originated fine secretory granules, and an eccentric nucleus. Plasmatocytes were easily characterized by their variable shapes and irregular outline with pseudopodia-like cytoplasmic extensions, possession of an elongated lobed nucleus, multivesicular bodies, RER-derived membrane bounded, electron-dense, lysosomelike vacuoles, well-developed SER cisternae, and numerous pinocytic and SER-originated vesicles of different sizes along the peripheral region. M-granulocytes comprised the largest proportion of hemocytes in all samples observed. M-granulocytes were distinguished not only by the presence of membrane bounded granules of different sizes and electron density, but by the possession of large nuclei with distinct nucleoli, many mitochondria, and a highly developed network of rough endoplasmic reticulum (RER). M-granulocytes had abundant, rosette-shaped, RER-derived chains of fine secretory granules, which accumulated in the cytoplasm and vacuoles, and were ultimately deposited into the hemolymph by exocytosis. These fine granules gave a positive result with periodic acid-Schiff (PAS) test. Based on RER-synthesized fine secretory granules (M-granulocytes), their ultimate deposition into hemolymph, the red pigmentation of hemolymph, positive PAS histochemical test of these granules, and the high population of these hemocytes, no such cell type has been described in previous studies in insects. The sub-cellular structure of the granulocyte in this insect has been modified to perform a special synthetic and secretory function (i.e., possibly the synthesis of the red pigment found in hemolymph, which has been the source of commercially important cochineal dye).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01273892
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    Electronic Resource
    Electronic Resource
    Structure and development of cell connections in the phloem ofMetasequoia glyptostroboides needles I. Ultrastructural aspects of modified primary plasmodesmata in Strasburger cells (1996)
    Springer
    Protoplasma 193 (1996), S. 191-203 
    Details
    ISSN: 1615-6102
    Keywords: Endoplasmic reticulum ; Metasequoia ; Phloem-loading ; Plasmodesmata ; Strasburger cells ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Symplasmic contacts of Strasburger cells in the mature needle ofMetasequoia glyptostroboides were analysed with special regard to changes of plasmodesmata in fine structure and distribution. In meristematic cells simple primary plasmodesmata are evenly distributed throughout the entire wall, whereas in mature Strasburger cells plasmodesmata are aggregated in defined, dome-shaped wall thickenings. The elongated, often multiple-branched cytoplasmic strands show a distinct neck region besides a considerably dilated sleeve region confluent with cavities, which have formed at branching sites of plasmodesmata in various planes of the wall thickening. Most branches radiating from these cavities connect the protoplasts of the adjacent cells; occasionally some strands are discontinuous. The desmotubules of both, continuous and discontinuous plasmodesmal branches exhibit great variability in structure and number: they may be partially dilated, multiple-stranded and branched within single plasmodesmal branches. Fine structurally, plasmodesmata of Strasburger cells show great resemblance with developing sieve pores of conifers. This characteristic fine structure implicates a special role of the endomembrane system for phloem loading in theMetasequoia leaf.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01276645
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  • 48
    Electronic Resource
    Electronic Resource
    Dynamics of vegetative cytoplasm during generative cell formation and pollen maturation inArabidopsis thaliana (1996)
    Springer
    Protoplasma 194 (1996), S. 81-90 
    Details
    ISSN: 1615-6102
    Keywords: Arabidopsis ; Pollen ; Vegetative cytoplasm ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Ultrastructural changes of pollen cytoplasm during generative cell formation and pollen maturation inArabidopsis thaliana were studied. The pollen cytoplasm develops a complicated ultra-structure and changes dramatically during these stages. Lipid droplets increase after generative cell formation and their organization and distribution change with the developmental stage. Starch grains in amyloplasts increase in number and size during generative and sperm cell formation and decrease at pollen maturity. The shape and membrane system of mitochondria change only slightly. Dictyo-somes become very prominent, and numerous associated vesicles are observed during and after sperm cell formation. Endoplasmic reticulum appears extensively as stacks during sperm cell formation. Free and polyribosomes are abundant in the cytoplasm at all developmental stages although they appear denser at certain stages and in some areas. In mature pollen, all organelles are randomly distributed throughout the vegetative cytoplasm and numerous small particles appear. Organization and distribution of storage substances and appearance of these small particles during generative and sperm cell formation and pollen maturation are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01273170
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    Changes in the structure ofArabidopsis thaliana during female development of the plant-parasitic nematodeHeterodera schachtii (1996)
    Springer
    Protoplasma 194 (1996), S. 103-116 
    Details
    ISSN: 1615-6102
    Keywords: Arabidopsis thaliana ; Cyst nematodes ; Development ; Histology ; Syncytium ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary The beet cyst nematodeHeterodera schachtii is able to establish a feeding structure (syncytium) in the vascular tissue of roots and shoots ofArabidopsis thaliana. Histological and ultrastructural studies were performed to assess plant responses during the development of juvenile females under monoxenic conditions. After destructively invading a root the nematode selects and pierces a single procambial cell with its stylet and transforms it into an initial syncytial cell (ISC) by secretory activity. The first most obvious changes in the ISC occur in the vacuolar system and at the wall. Differentiation of a central vacuole is impeded resulting in the formation of numerous small vacuoles. Multivesicular and paramural bodies are formed. An electron translucent material is deposited on the cell wall. Partial dissolution of the cell wall leads to the formation of a syncytium. At the juveniles' last pre-adult developmental stage the syncytium attains its maximum longitudinal and radial extension, occupying a major part of the central cylinder. Its features are indicative of a very high level of metabolic activity. The hypertrophied syncytium is ensheathed by a peridermal cover in which secondary xylem and phloem elements are interspersed. When females die the syncytia degenerate. The ultrastructural and histological features of syncytia described from roots are also found in syncytia induced in aerial parts of the plant.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01273172
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  • 50
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    Morphological variability of smooth muscle cells in human nasal swell bodies (1996)
    Springer
    European archives of oto-rhino-laryngology and head & neck 253 (1996), S. 147-151 
    Details
    ISSN: 1434-4726
    Keywords: Nasal swell bodies ; Morphology ; Smooth muscle cell ; Ultrastructure
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The complex functional behavior of nasal swell bodies is still not completely understood. In the present study the histology of the vessels involved in the swelling mechanism is examined and the ultrastructural appearances described of the different types of smooth muscle cells located in the vascular wall of swell bodies in the human inferior turbinate. Even though the majority of smooth muscle cells of the nasal swell bodies showed a normal, elongated appearance comparable to other smooth muscle cells elsewhere in the body, a variety of cells with atypical shapes could be detected that have not been described previously in vessels of the nasal mucosa. The diameters of the smooth muscle cells in general were strikingly variable. The individual smooth muscle cells were surrounded by a basal lamina that was occasionally disrupted or doubled. Myoblasts were separated by a connective tissue space containing collagen fibrils, mature elastin fibers and bundles of microfibrils. The latter two types of fibers and fibrils occurred mainly in the outer parts of the muscular coat. The endowment of cytoplasmic components was similar in all smooth muscle cells of the vascular wall in the swell bodies. These findings indicate that the specific feature of smooth musculature presumably resides in the unusual morphological variability of the single cells present, as well as in the striking heterogeneity of the arrangement of bundles of these cells in the vascular wall.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00615112
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    Intermittent compressive load stimulates osteogenesis and improves osteocyte viability in bones cultured “in vitro” (1996)
    Springer
    Clinical rheumatology 15 (1996), S. 563-572 
    Details
    ISSN: 1434-9949
    Keywords: Organ Culture ; Intermittent Compressive Force ; Osteogenesis ; Ultrastructure ; Osteocyte
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The effect of mechanical stresses on osteogenesis, the viability of osteocytes and their metabolic activity in organ culture of bones intermittently loaded “in vitro” are reported. Metatarsal bones, isolated from 12-day-old rats, were cultured in BGJb medium (with 10% foetal calf serum, 75µg/ml of ascorbic acid, 100 U/ml of penicillin and 100µg/ml of streptomycin), in humidified air enriched by 5% CO2 and 30% O2, and loaded in our original device for 1/2 an hour at 1 Hz. homotypic isolated and unloaded bones, cultured in the same medium, were taken as controls. The ALP (alkaline phophatase activity) increases in the media of loaded bones in comparison with the control bones. The percentage of viable osteocytes is significantly greater in loaded than in control bones. TEM observations demonstrate that in both loaded and control unloaded bones, osteocytes show well developed organelle machinery and several gap junctions with adjacent cellular processes. In the cells of loaded bones, however, a higher number of cytoplasmic organelles and gap junctions were found. In particular, RER increases twice, gap junctions three times. The induced osteogenesis and the TEM observations demonstrate the suitability of this experimental model and support the recent advanced hypothesis according to which the mechanical loading may exert a trophic function on osteocytes, stimulating both the proteic synthesis in the above-mentioned cells and the cell-to-cell communication. Furthermore, the loading is likely to exert a biological stimulus on osteoblasts via signalling molecules produced by osteocytes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02238545
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    Fullerene-Acetylene Molecular Scaffolding: Chemistry of 2-functionalized 1-ethynylated C60, oxidative homocoupling, hexakis-adduct formation, and attempted synthesis of C1242- (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 6-20 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the way to the fullerene-acetylene hybrid carbon allotropes 2 and 6, the oxidative homocoupling of the 2-functionalized 1-ethynylated C60 derivatives 11, 12, 14, and 15 was investigated. Under Glaser-Hay conditions, the two soluble dumbbell-shaped bisfullerenes 17 and 18, with two C60 moieties linked by a buta-1,3-diynediyl bridge, were formed in 52 and 82% yield, respectively (Scheme 2). Cyclic-voltammetric measurements revealed that there is no significant electronic communication between the two fullerene spheres via the buta-1,3-diynediyl linker. Removal of the 3,4,5,6-tetrahydro-2H-pyran-2-yl (Thp) protecting groups in 18 gave in 80% yield the highly insoluble dumbbell 19 with methanol groups in the 2,2′-positions of the buta-1,3-diynediyl-bridged carbon spheres. Attempted conversion of 19 to the all-carbon dianion 6 (C1242-) via base-induced elimination of formaldehyde was not successful presumably due to exo-dig cyclization of the formed alkoxides. The occurrence of this cyclization under furan formation was proven for 2-[4-(trimethylsilyl)buta-1,3-diyn-1-yl][60]fullerene-1-methanol (21), a soluble model compound for 19 (Scheme 3). To compare the properties of ethynylated fullerene mono-adducts to those of corresponding higher adducts, hexakis-adducts 26 and 28 with an octahedral functionalization pattern resulting from all-e (equatorial) additions were prepared by the reversible-template method of Hirsch (Scheme 4). Reaction of the ethynylated mono-adducts 25 or 13 with diethyl 2-bromomalonate/1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in the presence of 1,9-dimethylanthracene (DMA) as reversible template led to 26 and 28 in 28 and 22% yield, respectively. Preliminary experiments indicated a significant change in reactivity and NMR spectral properties of the fullerene addends with increasing degree of functionalization.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790103
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    Oligonucleotide Synthesis on Polystyrene-Grafted Poly(tetrafluoroethylene) Support (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 137-150 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Supports consisting of a thin layer (2-10%) of polystyrene (PS) grafted onto a poly(tetrafluoroethylene) (PTFE) core are an interesting alternative to controlled pore glass (CPG) carriers in oligonucleotide synthesis. The beads are mechanically stable, do not show significant swelling, and allow effective removal of substrates by short washing steps with organic solvents. PTFE-PS as an organic polymer has generally more hydrophobic properties than inorganic polymer supports and, therefore, is well compatible with organic solvents such as anhydrous MeCN. We found PTFE with a content of 2-3% PS graft to be a very good support for the synthesis of oligonucleotides of extended length. In comparison, PTFE with 5-10% grafted PS is especially useful for large-scale syntheses. Functionalization procedures minimized in the extent of side reactions are described as well as examples for the use of the supports in syntheses of oligonucleotides both on large scale and of extended chain length.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790115
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  • 54
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    Säure-Additionen an ‘Push-Pull’-Enine. Erste Beobachtung einer Umlagerung von 5-Chloro-5-(dialkylamino)pentadienalen30. Mitteilung über Aminoacryl-Derivate. 29. Mitteilung: [1]. (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 192-202 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reaction of ‘Push-Pull’ Enynes with Acids. First Observation of a Rearrangement of 5-Chloro-5-(dialkylamino)pentadienals‘Push-pull’-enynes 7 react easily with HCl as well as with AcOH to give 5-amino-5-chloropentadienals 8 and 5-(acetoxy)-5-aminopentadienals 13 as well as the corresponding ketones. In view of a postulated rearrangement of compounds 8 and 13 (Scheme 2), both types of compounds have been treated with traces of acid. While no definite reaction is observed in case of 13, HCl-addition products 8 easily and quantitatively rearrange to give 2H-pyran-2-iminium chlorides 10 which are the postulated intermediates of the rearrangement 8→12 (Scheme 2).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790119
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  • 55
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    The Self-Recognition and Self-Assembly of Folic Acid Salts in Isotropic Water Solution (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 220-234 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The self-assembly of alkaline folates in isotropic water solutions, with or without added salts, has been investigated by small-angle neutron-scattering, circular-dichroism, and NMR techniques. The assembled species are chiral, cylindrical aggregates of finite length, composed of stacked tetramers; each tetramer is formed by Hoogsteen-bonded folate residues. The assembly process is more efficient in the presence of an excess of NaI ions, leading to longer aggregates with stronger tetramer-tetramer-tetramer interaction. In pure water, the rods are shorter and the tetramer-tetramer interaction weaker. Association between folates can be detected by circular-dichroism spectroscopy starting from a concentration of 6· 10-4 mol l-1, well below the critical concentration for the formation of the cholesteric mesophase (ca. 0.5 mol l-1).
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790123
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    Oligosaccharide Analogues of Polysaccharides. Part 6. Orthogonal protecting/activating groups in an improved binomial synthesis of ‘acetyleno-oligosaccharides’ (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 255-268 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Bromination of the monosilylated dialkynylated monomer 1a (Scheme 1), dimer 3 and tetramer 5 by N-bromosuccinimide (NBS) in the presence of CF3COOAg gave 2, 4, and 6, respectively, in over 93%. Similar conditions led to bromodesilylation. Either silyl group of the diprotected monomer 1c was selectively removed by bromolysis. On the one hand, bromodesilylation of 1c gave 2 in yields varying between 80 and 99%. On the other hand, bromodesilylation of 7, obtained from 1c by hydrolytic removal of the tetrahydro-2H-pyran-2-yl (Thp) group, yielded 91% of 8. Mechanistic considerations suggested that the deprotective bromination should be improved by replacing the Me3Si by a Me3Ge group. Indeed, bromodegermylation of 1b was quantitative and ca. 60 times faster than bromodesilylation of 1c. The Me3Si and Me3Ge groups can be used for an orthogonal protection/activation of dialkynes. This was shown by desilylating 12 to 11 (Scheme 2), while bromination yielded 13. Both reactions proceeded in high yields; 9 was isolated as a minor by-product of 13. The reactivity towards bromolysis decreases in the series H-DOPS 〉 Me3Ge ≈ H 〉 Me3Si 〉 Thp-DOPS (DOPS = [dimethyl(oxy)-p ropyl]dimethylsilyl). Orthogonal bromolysis of DOPS- and Me3Ge-substituted dialkynes is slightly more selective than the one of Me3Si- and Me3Ge-substituted analogues. Coupling of 7 with the bromoalkyne 2 gave the dimer 15 (76%), 14 (2%), and 16 (4%) (Scheme 3). The binomial synthesis was optimized so that each cycle, doubling the size of the precursor, requires the minimal number of transformations (Scheme 4). The orthogonally protected monomer 1b, dimer 19, and tetramer 22 were, on the one hand, hydrolyzed to the alcohols 18 (95%), 21 (91%), and 24(91%), respectively, and, on the other hand, bromodegermylated to 2 (99%), 4 (97%), and 6(93%). Cross-coupling of 18 with 2, 21 with 4, and 24 with 6 gave the orthogonally protected dimer 19 (73%), tetramer 22 (87%), and octamer 25 (83%), respectively.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790126
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    Novel Thiazole-Containing Complexing Agents and Luminescence of Their Europum(III) and Terbium(III) Chelates (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 295-306 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of novel thiazole-containing complexing agents and their luminescence properties with EuIII and TbIII ions are reported. One of these terpyridine analogues was also tested as an EuIII labelling reagent, and its luminescence properties as an antibody conjugate were studied.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790129
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    Masthead (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790201
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  • 59
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    Corniculoside, a New Biosidic Ester Secoiridoid from Halenia corniculata (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 363-370 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemical screening of the secondary metabolites from Halenia corniculata L. (CORNAZ), by LC/UV,LC/TSP-MS (thermospray), and LC/ES-MS (electrospray) was used for the targeted isolation of corniculoside (1), a new biosidic ester secoiridoid. The structure was established as 7-β-[(E)-4′-O-(β-D-glucopyranosyl)caffeoyloxy]-sweroside by 1D- and 2D-NMR, LC/UV, LC/MS, and FAB-MS data, in combination with chemical reactions.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790205
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  • 60
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    New Addition Reactions of Organometal Compounds with 4,4-Dimethyl-1,3-thiazole-5(4H)-thionesDedicated to Professor H. Suschitzky on the occasion of his 80th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 371-384 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Addition reactions of organometallic reagents with 4,4-disubstituted 1,3-thiazole-5(4H)-thiones were studied. Whereas the reactions with alkyllithium and alkyl Grignard reagents occurred in the thiophilic manner, the carbophilic addition was observed with allyllithium and allyl Grignard reagents. A radical reaction mechanism is proposed for rationalizing these observations (Scheme 5). A radical cyclization of the prepared 5-allyl-4,5-dihydro-1,3-thiazole-5-thiol derivatives yielded 1,6-dithia-3-azaspiro[4.4]non-2-enes (Table 4).
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790206
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    Synthesis of Highly Fluorinated Di-O-alk(en)yl-glycerophospholipids and Evaluation of Their Biological Tolerance (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 405-425 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The syntheses of various fluorocarbon/fluorocarbon and fluorocarbon/hydrocarbon rac-1,2- and 1,3-di-O-alk(en)ylglycerophosphocholines and rac-1,2-di-O-alkylglycerophosphoethanolamines (see Fig.2), which may be used as components for drug-carrier and delivery systems, are described together with some results concerning their biological tolerance. They were obtained by phosphorylation of perfluoroalkylated rac-di-O-alk(en)ylgly-cerols using POCl3, then condensation with choline tosylate or N-Boc-ethanolamine (2-[(tert-butoxy)carbonyl-amino]ethanol) followed by Boc-deportection (Schemes 6-8). The fluorcarbon/fluorocarbon 1,2-di-O-alkylgly-cerols were prepared by O-alkylation of rac-1-O-benzylglycerol using perfluoroalkylated mesylates, then hydrogenolysis for benzyl deprotection (Scheme 1). The two different hydrophobic chains in the mixed fluorocarbon/fluorocarbon and fluorocarbon/hydrocarbon 1,2-di-O-alk(en)ylglycerols were introduced starting from 1,2-O-iso-propylidene- then O-trityl-protected glycerols or from 1,3-O-benzylidene-glycerol (Schemes 3 and 4). The perfluoroalkylated O-alkenylglycerols were obtained by O-alkylation of a glycerol derivative using an ω-unsaturated alkenyl reagent, the perfluoroalkyl segment being connected onto the double bond in a subsequent step (Schemes 1) and 3. The perfluoroalkylated symmetrical and mixed 1,3-di-O-alkylglycerols were synthesized by displacement of the Cl-atom in epichlorohydrin by perfluoroalkylated alcohols, then catalytic (SnCl4) opening of the oxirane ring of the resulting alkyl glycidyl ethers in neat alcohols (Scheme 5). When injected intravenously into mice, acute maximum tolerated doses higher than 1500 and 2000 mg/kg body weight were observed for the fluorinated glycerophosphocholines, indicating a very promising in vivo tolerance.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790209
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    Diazoaldehyde Chemistry. Part 3Part 1: [1a]; Part 2: [1b].. Synthesis of 4-acyl-1H-1,2,3-triazole derivatives (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 449-453 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ten new α-diazo-β-oxoaldehydes were condensed with aniline, ammonia, hydroxylamine, and semicarbazide to yield new 4-acyl-(1-substituted)-1H-1,2,3-triazoles in moderate-to-good yields. The method is simple and regiospecific. The latter feature makes this method superior to the widely used acylacetylene + azide approach.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19960790212
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  • 63
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    N7-DNA: Synthesis and Base Pairing of Oligonucleotides Containing N7-(2-Deoxy-β-D-erythro-pentofuranosyl)guanine (N7Gd) (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 477-487 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of oligonucleotides containing N7-(2-deoxy-β-D-erythro-pentofuranosyl)guanine (N7Gd; 1) is described. Compound 1 was prepared by nucleobase-anion glycosylation of 2-amino-6-methoxypurine (5) with 2-deoxy-3,5-di-O-(4-toluoyl)-α-D-erythro-pentofuranosyl chloride (6) followed by detoluoylation and displacement of the MeO group (8→10→1). Upon base protection with the (dimethylamino)methylidene residue (→11) the 4,4-dimethoxytrityl group was introduced at OH—C(5′) (→12). The phosphonate 3 and the phosphoramidite 4 were prepared and used in solid-phase oligonucleotide synthesis. The self-complementary dodecamer d(N7G—C)6 shows sigmoidal melting. The Tm of the duplex is 40°. This demonstrates that guanine residues linked via N(7) of purine to the phosphodiester backbone are able to undergo base pairing with cytosine.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790215
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    Studied Directed toward the Synthesis of Phomenoic Acid. Part 2Part 1: [1].. Stereocontrolled Synthesis of the C(7)-to-C(14) Segment (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 518-526 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from the esters (2E,4S)-6 and (2E,4R)-6, bromo aldehydes (S)-9 and (R)-9 as well as bromo alcohols (S)-10 and (R)-10, respectively, were prepared. Bromo alcohol (R)-8 was converted to the diol (2E,4R)-16. Ozonolysis of the latter led to aldehyde (R)-17, which was transformed, by a Wittig reaction, to (2R,4E,6R)-18, corresponding to the C(7)-to-C(14) segment of phomenoic acid (1). Attempts to improve the yields by applying a Julia coupling of (R)-23, which was prepared from (2E,4R)-7, with (R)-24 were unsuccessful. Finally, the coupling of the iodo derivative (2E,4S)-28 with the lithiated derivative of 1,3-dithiane 30 by the Corey-Seebach ‘Umpolung’ led to (3S,4E)-32 which is a derivative of the C(7)-to-C(14) segment of 1, suitable for further transformations.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790219
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    Channel-Forming Activity of 3-Hydroxybutanoic-Acid Oligomers in Planar Lipid BilayersDedicated to Prof. Dr. Edgar Heilbronner on the occasion of his 75th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 507-517 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Monodisperse and polydisperse oligomers and polymers of 3-hydroxybutanoic acid (3-HB) containing 8, 16, ca. 28, 32, ca. 60, 64, 96, and ca. 3000 monomer units were incorporated into palmitoyl-oleoyl-phosphatidyl choline (POPC) planar bilayers. At concentrations of 0.1-5% of oligo(3-HB), the resulting phospholipid bilayers showed typical single-channel behavior for Rb+ and Ba2+ ions, using the patch clamp technique. Thus, channel-forming activity of a pure polyester has been demonstrated for the first time (Figs. 1, 3, and 6). Single-channel activity depends upon the following structural parameters of the 3-HB derivatives: unprotected OH and COOH groups on the chain ends; chain length ≥ 16 monomer units; no high-molecular-weight as in P(3-HB). The results are discussed in view of the Ca2+-specific channel formed with the P(3-HP)/Ca · PPi complex from genetically competent Escherichia coli and in view of the ubiquitous occurrence of low-molecular-weight P(3-HB) in prokaryotic and eukaryotic organisms. A simple model for the channel-causing structure is proposed, based on the proven tendency of oligo- and poly(3-HB) to form ca. 50-Å thick lamellar crystallites.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790218
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    Mitteilungen (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 568-570 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790224
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  • 67
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    Synthese der p-CumaroylspermidineProf. Edgar Heilbronner zum 75. Geburtstag gewidmet (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 548-559 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Synthesis of p-CumaroylspermidinesThe synthesis of three mono[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines, 10, 20, and 28, three bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines, 6, 16, and 25, and one tris[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]-spermidine is described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790222
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  • 68
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    Further C-Alkylations of Cyclotetrapeptides via Lithium and Phosphazenium (P4) Enolates: Discovery of a New Conformation (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 588-608 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Four cyclotetrapeptides containing one (1, 2) or two (3, 4) chiral amino acids have been C-alkylated or C-hydroxyalkylated through Li+ or phosphazenium (P4 · H+) enolates. The reactions are completely diastereoselective (by NMR or HPLC analysis) with respect to the newly formed backbone stereogenic centres (Tables 2 and 3). The reactivity of the polylithiated species responsible for these alkylations is such that only highly reactive electrophiles (MeI, BnBr, primary allylic halides, aldehydes, CO2) can be employed. It is shown that the position, and thus the chirality sense, of the newly formed stereogenic centre in a given cyclotetrapeptide backbone is controlled by the positioning of N-methyl groups in the starting material (cf. cyclo(-MeLeu-Gly-D-Ala-Sar-) (3) and cyclo(-Leu-Sar-MeDAla-Gly-) (4) in Scheme 1). With Schwesinger's phosphazene P4-base, all NH groups are first benzylated and C-benzylation then takes place at a sarcosine, rather than an N-benzylglycine residue (Table 3). In contrast to open-chain N-benzyl peptides, the N-benzylated cyclotetrapeptides could not be debenzylated under dissolving-metal conditions (Na/NH3). Conformational analysis (NMR spectroscopy and X-ray diffraction) shows that the prevailing species have cis/trans/cis/trans(ctct) peptide bonds (zigzag conformation of Ci backbone symmetry, Figs. 2-4). However, a hitherto unknown conformation of cyclotetrapeptides has been found in CDCl3 solutions of the hydroxyalkylated products 18-21 (obtained with EtCHO and PhCHO as electrophiles; Fig.4). The new conformation has four trans peptide bonds and is believed to result mainly from intramolecular H-bond formation, involving the newly generated alkyl- or arylserine residue. This assumption has also been supported by modelling (TRIPOS force field, SYBYL, see Fig.5 and Table 6). The structure may be considered as a β-turn mimic.
    Additional Material: 5 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790303
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    1,1,2,2-Tetraethynylethanes: Synthons for Tetraethynylethenes and Modules for Acetylenic Molecular ScaffoldingDedicated to Nikolai S. Zefirov on the occasion of his 60th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 634-645 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of functionalized 1,1,2,2-tetraethynylethanes (= 3,4-diethynylhexa-1,5-diynes) as synthons for tetraethynylethenes (3,4-diethynylhex-3-ene-1,5-diynes) and as building blocks for three-dimensional acetylenic molecular scaffolding targeting the synthesis of the molecular carbon belts 3 and 4 is reported (Scheme 1). Reaction of diethyl oxalate and (trialkylsilyl)ethynyl Grignard reagents afforded the silyl-protected 3,4-diethynylhexa-1,5-diyne-3,4- diols 7 and 8 which were transformed in high yields into the cyclic carbonate 9 and the cyclic orthoesters 10-13, respectively (Scheme 2). The solid-state structures of 9 and 10 were elucidated by X-ray crystallography. The alkyne protecting groups in 9, 10, and 12 were smoothly removed to give the free tetraynes 14-16 as relatively stable oils in nearly quantitative yields (Scheme 3). Orthoesters 15 and 16 underwent Pd-catalyzed cross-coupling with iodobenzene to give the tetraphenyl derivatives 17 and 18 (Scheme 4). Thermal acid-catalyzed elimination of the orthoester moieties in 12 and 13 produced the silyl-protected tetraethynylethenes 19 and 20 and concluded a novel, simple three-step synthesis of these fully two-dimensionally conjugated π-chromophores (Scheme 5).
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790306
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  • 70
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    Synthesis of Carbocyclic C-Nucleosides Containing Nonnatural Pyrimidine Bases (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 702-709 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of new carbocyclic C-nucleosides with a cis-4′-(hydroxymethyl)cyclopent-2′-enyl sugar moiety and unnatural pyrimidine bases (2-6) were synthesized in racemic form in two steps starting from the easily accessible cyclic carbonate 1.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790312
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  • 71
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    First Fullerene[60]-Containing Thermotropic Liquid Crystal. Preliminary Communication (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 736-741 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and liquid-crystalline and thermal properties of a fullerene[60] functionalized by a framework containing two cholesterol derivatives through a methanofullerene structure are reported. The targeted fullerene derivative showed high thermal stability.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790316
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  • 72
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    Nucleic-Acid Analogs with Restricted Conformational Flexibility in the Sugar-Phosphate Backbone (‘Bicyclo-DNA’). Part 6Part 5: [1].. Probing the influence of torsion angle γ on DNA-duplex stability: Syntheis and properties of oligodeoxynucleotides containing [(3′S,5′S)-2′-deoxy-3′,5′-ethano-β-D-ribofuranosyl]adenine and -thymine (‘5′-epi-bicyclodeoxynucleosides’)Prelimimanry communication: [2]. (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1129-1146 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the thymine- and adenine-containing 5′-epi-bicyclodeoxynucleosides 7 and 8 as well as of the corresponding building blocks 13 and 14 for oligonucleotide syntheis according to the phosphoramidite methodology is described. A conformational analysis of 7 and 8 by 1H-NMR spectroscopy, refined by molecular modeling, shows the preferred conformation of the furanose unit in these nucleosides to be of the 1′-exo/2′-endo type. The 5′-OH group on the carbocyclic ring prefers to be axially oriented, thus placing torsion angle γ in the unusual -syn-clinal (-sc) range. These epi-bicyclodeoxynucleosides were successfully incorporated into DNA decamers. From UV/melting curves of such decamers with DNA and RNA complements, a duplex destabilization of -2 to -9° per residue was observed. An oligonucleotide built completely from 5′-epi-bicyclothymidine shows no detectable affinity to its DNA or RNA complement anymore. CD Spectra of duplexes containing 5′-epi-bicyclodeoxynucleotide units are very similar to the natural reference systems, indicating no major structural changes. A molecular-dynamics simulation of a heptamer duplex containing one 5′-epibicyclothymidine residue in the center reveals a conformational change of its carbocyclic unit placing torsion angle γ in the (for the free mononucleoside unfavorable) -anti-clinal (-ac) conformation in the duplex. The role of torsion angle γ on DNA duplex stability is discussed.
    Additional Material: 8 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790421
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    The Enantioselective Synthesis of β-Amino Acids, their α-hydroxy derivatives, and the N-terminal components of bestatin and microginin (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1203-1216 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: L-Aspartic acid by tosylation, anhydride formation, and reduction with NaBH4 was converted into (3S)-3-(tosylamino)butan-4-olide (8; Scheme 1). Tretment of 8 with ethanolic trimethylsilyl iodide gave the N-protected deoxy-iodo-β-homoserine ethyl ester 9. The latter, on successive nucleophilic displacement with lithium dialkyl-cuprates ( → 10a-e), alkaline hydrolysis ( → 11a-e), and reductive removal of the tosyl group, produced the corresponding 4-substituted (3R)-3-aminobutanoic acids 12a-e (ee 〉 99%). Electrophilic hydroxylation of 8 ( → 19; Scheme 3), subsequent iodo-esterification ( → 21; Scheme 4), and nucleophilic alkylation and phenylation afforded, after saponification and deprotection, a series of 4-substituted (2S, 3R)-3-amino-2-hydroxybutanoic acids 24 including the N-terminal acids 24e ( =3) and 24f ( =4) of bestatin and microginin (de 〉 95%), respectively.
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19960790426
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    A New Textual Analysis of the Prelog Erlkönig Legend: An Interdisciplinary Approach to Scientific History and Literary Criticism (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1241-1248 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790502
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  • 75
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    Total Synthesis of (+)-(8S,13R)-CyclocelabenzineDedicated to Professor Vladimir Prelog on the occasion of his 90th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1295-1304 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An asymmetric synthesis of the spermidine alkaloid (+)-cyclocelabenzine (1a) and its (-)-(13S)-epimer 1b is described using optically active (+)-(3S)-3-amino-3-phenylpropionic acid as the chiral building block. The isoquinolin-1-one fragment 15 was synthesized by a modified Bischler-Napieralski reaction. The relative configuration of the (-)-isomer was determined by an X-ray crystal-structure analysis, which enabled us to determine the absolute configuration of natural (+)-1a as (8S,13R).
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790506
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  • 76
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    A Reinvestigation of the Oxidative Rearrangement of Yohimbane-Type Alkaloids. Part BPart A: [1].. Formation of Oxindol (= 1,3-Dihydro-2H-indol-2-one) Derivatives (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1361-1378 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The methanolysis of the epimeric 7-chloro-7H-yohimbine derivatives 2 and 3 was reinvestigated. In case of the 7α-epimer 2, the reaction was uneventful and conformed with earlier observations, i.e., under sufficiently mild conditions, only the imino ether 4 (= imino ether A) was produced. Under the same conditions, the less reactive β-isomer 3 furnished a mixture of both imino ethers 4 and 5, accompanied by the elimination product 11, and by equal amounts of yohimbine (1) and 3,4,5,6-tetradehydroyohimbine (12), which are believed to arise through a disproportionation process of the putative intermediate 5,6-didehydroyhimbine (23). The nature of this divergent reactivity and of the ready equilibration of 4 and 5 was investigated by means of extensive force-field and semi-empirical calculations (AM1 and PM3) of various conformers of the compounds 2-5 and of some possible reaction intermediates.
    Additional Material: 7 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790510
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  • 77
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    2-Alkynylcyclopent-2-enols from 2-Alkynylcyclohex-2-enones via 1-Alkynyl-7-oxabicyclo[4.1.0]heptan-2-ones (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1428-1434 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Alkynylcyclohex-2-enones 1a-c and 2a-c react with H2O2/NaOH in MeOH to afford 1-alkynyl-7-oxabicyclo[4.1.0]heptan-2-ones 3a-c and 4a-c, respectively. The 3-unsubstituted bicyclic epoxy ketones 3a, 3b, and 4a, 4b react further with H2O2/NaOH, undergoing ring contraction and (formal) decarbonylation to give 2-alkynylcy-clopent-2-enols 5a, 5b, and 6a, 6b, respectively. Epoxy ketones 3 are also obtained under neutral conditions on irradiation (λ = 350 nm) of cyclohexenones 1 in air-saturated benzene solution. Similarly, under neutral conditions oxo-cycloalkenecarbonitriles 8 react (thermally) with H2O2 in MeCN to give the oxabicyclic carbonitriles 9.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790515
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    Xylose-DNA Containing the Four Natural Bases (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1451-1461 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Oligonucleotides containing (2′-deoxy-β-D-xylofuranosyl)guanine have been prepared. For this purpose 2-aminoadenosine (5) was synthesized and converted to 2′-deoxy-β-D-xyloguanosine (1). The related 2′-deoxy-β-D-xyloisoguanosine (3) and 2′-deoxy-β-D-xyloxanthosine (4) were also synthesized. Compound 1 was converted to the phosphonate and phosphoramidite building blocks 10 and 11, respectively. The oligodeoxynucleotide (5′-3′)d(xG-xT-xA-xG-xA-xA-xT-xT-xC-xT-xA-xC-T) (18) formed a duplex with the same Tm as the parent (5′-3′)-(G-T-A-G-A-A-T-T-C-T-A-C) (19), but with an inverted CD spectrum.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790518
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    Masthead (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996) 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790601
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    Biosynthesis of Dodecano-4-lactone in Ripening Fruits: Crucial Role of an Epoxide-Hydrolase in Enantioselective Generation of Aroma Components of the Nectarine (Prunus persica var. nucipersica) and the Strawberry (Fragaria ananassa) (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1488-1496 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Early steps in the biosynthesis of dedecano-4-lactone in ripening nectarines (Prunus persica var. nucipersica) and strawberries (Fragaria ananassa) were studied using cis-9,10-([18O]epoxy)heptadecanoic acid (5), instead of the natural C18-precursor epoxystearic acid 1. In nectarines, an epoxide hydrolase catalyzed, in a highly regio- and enantioselective reaction, the attack of H2O at C(9) of epoxy acid 5 yielding preferentially (9R,10R)-dihydroxyheptadecanoic acid 6a as an early intermediate and, after further metabolization, undecano-4-lactone 7a. In strawberries, the same transformation exhibited only a moderate regio- and enantioselectivity. Besides the previously established function of phytogenic epoxide hydrolases involved in generating oxygenated fatty-acid derivatives, which are used in cutin monomer production and plant defence, a new rǒle for these enzymes now emerges in the enantioselective production of aroma components of ripening fruits. The cis-9,10-([18O]epoxy)heptadecanoic acid (≥ 98% 18O; 5) was obtained in good overall yield (68%) from isopropyl (9Z)-heptadec-9-enoate using 18O2 gas in a free-radical chain reaction in the presence of 2-methylbutanal.
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    URL: http://dx.doi.org/10.1002/hlca.19960790521
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    Synthese von Trifluoromethyl-substituierten Schwefel-Heterocyclen unter Verwendung von 3,3,3-Trifluorobrenztraubensäure-DerivatenVorgetragen von H. H. am ‘Symposium on Fluoroorganic Chemistry’, Warschau, 17. Mai 1996. (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1537-1548 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of Trifluoromethyl-Substituted Sulfur Heterocycles Using 3,3,3-Trifluoropyruvic-Acid DerivativesThe reaction of methyl 3,3,3-trifluoropyruvate (1) with 2,5-dihydro-1,3,4-thiadiazoles 4a, b in benzene at 45° yielded the corresponding methyl 5-(trifluoromethyl)-1,3-oxathiolane-5-carboxylates 5a, b (Scheme 1) via a regioselective 1,3-dipolar cycloaddition of an intermediate ‘thiocarbonyl ylide’ of type 3. With methyl pyruvate, 4a reacted similarly to give 6 in good yield. Methyl 2-diazo-3,3,3-trifluoropropanoate (2) and thiobenzophenone (7a) in toluene underwent a reaction at 50°; the only product detected in the reaction mixture was thiirane 8a (Scheme 2). With the less reactive thiocarbonyl compounds 9H-xanthene-9-thione (7b) and 9H-thioxanthene-9-thione (7c) as well as with 1,3-thiazole-5(4H)-thione 12, diazo compound 2 reacted only in the presence of catalytic amounts of Rh2(OAc)4. In the cases of 7a and 7b, thiiranes 8b and 8c, respectively, were the sole products (Scheme 3). The crystal struture of 8c has been established by X-ray crystallography (Fig.). In the reaction with 12, desulfurization of the primarily formed thiirane 14 gave the methyl 3,3,3-trifluoro-2-(4,5-dihydro-1,3-thiazol-5-ylidene)propanoates (E)-and (Z)-15 (Scheme 4). A mechanism of the Rh-catalyzed reaction via a carbene addition to the thiocarbonyl S-atom is proposed in Scheme 5.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790604
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    Duplex Stability of 7-Deazapurine DNA: Oligonucleotides containing 7-bromo- or 7-iodo-7-deazaguanine (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1549-1558 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The oligonucleotide building blocks, the phosphonates 1a, b and the phosphoramidites 2a, b derived from 7-iodo- and 7-bromo-7-deaza-2′-deoxyguanosines 3a, b were prepared. They were employed in solid-phase oligonucleotide synthesis of the alternating octamers d(Br7c7G-C)4 (8) and d(I7c7G-C)4 (9) as well as the homo-oligonucleotides d[(Br7c7G)5-G] (11) and d[(I7c7G)5-G] (12). The melting profiles and CD spectra of oligonucleotide duplexes were measured. The Tm values as well as the thermodynamic data were determined and correlated to the major-groove modification of this DNA. The self-complementary octamers 8 and 9 form more stable duplexes compared to the parent oligomer d(G-C)4. The heteroduplex of d[(I7c7G)5-G] (12) with d(C6) is slightly destabilized (ΔTm = -12°) over that of d[(c7G)5-G] with d(C6). However, the complex of 12 with poly(C) is more stable than that of d[(c7G5-G)] with poly(C).
    Additional Material: 4 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790605
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    The Crystal and Molecular Structure of [Co(tmen)3](C7H7SO3)3·2 H2O and [Co(tmen)3](CH3SO3)2·EtOH·1/2 H2O (tmen = 2,3-dimethylbutane-2,3-diamine) (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1607-1610 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The molecular structure of the two complex ions [Co(tmen)3]3+ and [Co(tmen)3]2+ (tmen = 2,3-dimethylbutane-2,3-diamine) have been determined at 100 K. They show a strong trigonal distortion of the octahedral CoN6 core. The twist angle is 26.2(2.8)° for CoII and 43.9(9)° for CoIII. Average Co—N distances are 2.193(13) Å (CoII) and 1.997(2) Å (CoIII), 0.02 Å longer than for the main body of CoIII amines.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790610
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  • 84
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    Hydrolytical Cleavage of TAR-RNA, the trans-Activation Responsive Region of HIV-1, by a Bis(guanidinium) Catalyst Attached to Arginine (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1967-1979 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Guanidinium compounds imitating the bis(arginine) structural motif of staphylococcal nuclease (e.g. 3) are known to be powerful catalysts for phosphoryl transfer reactions in dipolar aprotic solvents. Compound 3 also accelerates the hydrolysis of RNA (H2O, pH 7). However, due to diminished substrate affinity in H2O, the rate effects are less pronounced in aqueous than in aprotic solution. To test if a synthetic ribonuclease may be derived from the bis(guanidinium) moiety of 3 by the addition of RNA-binding substructures, the TAR sequence of HIV-1 was chosen as a target. The arginine residue of compound 4 serves as an extremely simplified mimic of tat, a protein responsible for boosting the viral transcription by complex formation with TAR. Here, we present the synthesis of 4 and its ability to bind and to cleave efficiently the truncated TAR sequence 1. In addition, the synthesis of an acridine arginine conjugate, 19, is reported in preliminary form. Compound 19 associates with 1 and completely blocks the cleavage induced by 4.
    Additional Material: 7 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790719
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  • 85
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    Lipid Masking and Reactivation of Angiotensin Analogues (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2023-2034 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Studies on post-angioplastic restenosis have shown the implication of angiotensin II (Ang) as a myoproliferative mediator. The antiproliferative efficacy of non-peptide Ang antagonists on the rat carotid model is of 50%, whereas a continuously infused peptide antagonist at low doses totally blocks neointimal growth. To explore the feasibility of depot forms of Ang that may be introduced during angioplasty and thus prevent restenois, lipid-masked Ang analogues of the following general structure were prepared: [Xxx°, Yyy1]Ang with Xxx = decanoyl or palmitoyl and Yyy = Ser, Cys, Asp, β-lactoyl, 3-mercaptopropanoyl or succinyl. All fatty acylated peptides [Xxx°, Yyy1]Ang were practically inactive, and O- or S-esterified Ser and Cys peptides underwent intramolecular transcylation giving inactive Nx-acylated peptides. O-Acylated [β-mercaptopropanoyl1]Ang were easily hydrolyzed into their biologically active[Yyy1]Ang forms, either by mild saponification or by lipase activity.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790723
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  • 86
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    From Inactive Nortopsentin D, a Novel Bis(indole) Alkaloid Isolated from the Axinellid Sponge Dragmacidon sp. from Deep Waters South of New Caledonia, to a Strongly Cytotoxic Derivative (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2075-2082 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Nortopsentin D (5), a bis(indole) alkaloid unique for bearing a 2-amino-methylimidazole appendage at the central 1H-imidazol-5(4H)-one nucleus, was isolated in abundance, besides the putative biogenetic precursor 6 of its appendage, from the deep-water axinellid sponge Dragmacidon sp. Structural elucidation of 5 by NMR and MS methods heavily relied on its N-methyl derivatives 8-11. Unusually for topsentin-type structures, natural 5 and semisynthetic methyl derivatives 8 and 10 proved inactive on KB tumoural cells, while introduction of the last three methyl groups, amazingly led to highly cytotoxic 11.
    Additional Material: 2 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19960790804
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  • 87
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    Model Studies for the Coenzyme-B12-Catalyzed Methylmalonyl→Succinyl Rearrangement. The Importance of Hydrophobic Peripheral Associations (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2100-2113 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The interaction between a vitamin B12 derivative containing a peripheral C18 alkyl chain (see 1a) and a (methyl)thiomalonate substrate bearing alkyl chains of various length at the thioester group (see 5) was investigated. A catalytic cycle was established for the methylmalonyl→succinyl rearrangement by using electrochemistry and photolysis (see Scheme 3). Increased yields of the succinate relative to the reduction product were obtained (2:3 ratio), when the reaction was run in MeOH/H2O, and when both the substrate and the catalyst had an octadecyl substituent capable of hydrophobic interactions.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790807
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  • 88
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    Electrospray-Ionization Mass Spectrometry. Part III.Part II:[1] Acid-Catalyzed Isomerization of N,N′-Bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines by the Zip ReactionPresented by L.B. at the ‘29. Diskussionstagung der Arbeitsgemeinschaft Massenspektrometrie der Deutschen Physikalischen Gesellschaft’, on May 28-31, 1996, University of Bremen, Germany. (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2152-2163 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The electrospray tandem mass spectra (ESI-MS/MS) of the three N,N′-bis[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]spermidines 1-3 displayed the same fragment-ion signals. These isomers could not be differentiated by ESI-MS/MS, since their fragmentation patterns are similar. (E,E)-N-(3-[15N]Aminopropyl)-3,3′-bis(4- hydroxyphenyl)-N,N′-(butane-1,4-diyl)bis[prop-2-enamide] ([15N(1)])-(1) was synthesized in order to get further information about the fragmentation mechanisms. The comparison of the ESI-MS/MS of 1 and [15N(1)]-1 revealed a transamidation, the Zip reaction, under mass-spectral conditions of the [1 + H]+ ions. Because of this reaction, the three isomers 1-3 could not be distinguished.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790810
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  • 89
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    Total Synthesis of Cyclothialidine (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2219-2234 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A total synthesis of cyclothialidine (1), a new DNA gyrase inhibitor isolated from Streptomyces filipinensis, is described. The synthetic concept was tested by preparing the lactone 13 (Scheme 2) which contains the characteristic bicyclic core entity of 1. Key features of the synthesis of 1 are: preparation of 3,5-dihydroxy-2,6-dimethylbenzoic acid (23) from 3,5-dihydroxybenzoic acid (19) by two consecutive Mannich aminomethylation/hydrogenation sequences; benzylic N-bromosuccinimide bromination of an ester derivative 25 thereof and its subsequent coupling with Boc-Ser-Cys-OMe (11); cyclization of the ω-hydroxy acid 29 29 to the 12-membered lactone 30 using preferably Mitsunobu conditions; completion of the peptidic side chains of 1 using Boc strategy (Scheme 4). Optically pure cis-N-(tert-butoxycarbonyl)-3-hydroxy-L-proline ((-)-14) was obtained by resolution of the racemate via an efficient reaction sequence containing a lipase-catalyzed enantiospecific acetate hydrolysis (Scheme 3). The structure of natural 1 was confirmed by comparison with the synthetic material. The synthetic route described provides also easy access to analogues of 1, e.g., via the intermediate 30.
    Additional Material: 1 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19960790816
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  • 90
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    Donor/Acceptor-Substituted Tetraethynylethenes: Systematic Assembly of Molecules for Use as Advanced Materials (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 2249-2281 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A comprehensive series of tetraethynylethenes (= 3,4-diethynylhex-3-ene-1,5-diynes, TEEs) bearing electrondonating (p-methoxyphenyl or p-aminophenyl) and/or electron-accepting (p-nitrophenyl) groups was prepared via [Pd]-catalyzed Sonogashira cross-coupling reactions. The electronic and photonic properties of these molecules were investigated with a special emphasis on the effects caused by degree and pattern of donor/acceptor substitution around the central TEE core. This analysis showed that intramolecular donor-acceptor interactions, as evidenced by a long-wavelength charge-transfer band, are considerably more effective in TEEs 44 and 46, with trans and cis, linearly-conjugated electronic pathways between donor and acceptor, than in 11, with a geminal, cross-conjugated electronic pathway. UV/VIS Spectroscopy revealed a steady bathochromic shift of the longest-wavelength absorption band (λmax) as the number of donor-acceptor conjugation paths increased upon changing from bis-arylated (11, 44, and 46) to tetrakis-arylated (14, 31, and 35) TEEs. The position of the longest-wavelength absorption was also found to be strongly dependent on the nature of the N-substituents in the R2NC6H4-donor groups. Electronic emission spectroscopic investigations demonstrated a considerable solvent dependency of the fluorescence of donor-acceptor-substituted TEEs such as 11 or 44, in agreement with the presence of highly polarized excited states in these molecules. Correspondingly, fluorescence spectra of TEEs bearing only donor or acceptor substituents showed little solvent dependency. The large majority of the donor/acceptor-substituted TEEs are thermally and environmentally stable molecules. They can be stored for months as solids in the air at room temperature, and many decompose only upon heating to temperatures above 200°. X-Ray analysis showed the conjugated C-atom scaffolds of 44, 46, and 67 to be essentially planar, whereas the aryl substituents in 28 and 30 are rotated out of the plane of the TEE core by varying degrees.
    Additional Material: 9 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790818
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  • 91
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    Mitteilungen (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 913-913 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790330
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  • 92
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    β-Peptides: Synthesis by Arndt-Eistert homologation with concomitant peptide coupling. Structure determination by NMR and CD spectroscopy and by X-ray crystallography. Helical secondary structure of a β-hexapeptide in solution and its stability towards pepsin (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 913-941 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The β-hexapeptide (H-β-HVal-β-HAla-β-HLeu)2-OH (2) was prepared from the component L-β-amino acids by conventional peptide synthesis, including fragment coupling. A cyclo-β-tri- and a cyclo-β-hexapeptide were also prepared. The β-amino acids were obtained from α-amino acids by Arndt-Eistert homologation. All reactions leading to the β-peptides occur smoothly and in high yields. The β-peptides were characterized by their CD and NMR spectra (COSY, ROESY, TOCSY, and NOE-restricted modelling), and by an X-ray crystal-structure analysis. β-Sheet-type structures (in the solid state) and a compact, left-handed or (M) 31 helix of 5-Å pitch (in solution) were discovered. Comparison with the analogous secondary structures of α-peptides shows fundamental differences, the most surprising one at this point being the greater stability of β-peptide helices. There are structural relationships of β-peptides with oligomers of β-hydroxyalkanoic acids, and dissimilarities between the two classes of compounds are a demonstration of the power of H-bonding. The β-hexapeptide 2 is stable to cleavage by pepsin at pH 2 in H2O for at least 60 h at 37°, while the corresponding α-peptide H-(Val-Ala-Leu)2-OH is cleaved instantaneously under these conditions. The implication of the described results are discussed.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790402
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  • 93
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    Novel Cholic-Acid-Type Sterones of Deltocyathus magnificus, a deep-water scleractinian coral from the Loyalty Islands, SW Pacific (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 982-988 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cholic-acid-type 3-keto steroids 1-8, all isolated from Deltocyathus magnificus (2-8 after CH2N2 treatment), are the first secondary metabolites obtained from a deep-water scleractinian. Steroids 1-3, 5, and 7 are new, their main structural oddities being loss of C(24) (see 5) or hydroxylation in the side chain (see 3 and 7). Steroids 4, 6, and 8, from the same coral, were previously known from other marine organisms.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790406
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  • 94
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    Acid-Catalysed Backbone Rearrangement of cholesta-6,8(14)-dienes (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 989-998 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Rearrangement of 5α- and 5β-cholesta-6,8(14)-dienes (13a and 13b, resp.) in the presence of anhydrous toluene-4-sulfonic acid in acetic acid leads to 5α- and 5β-12(13 → 14)-abeo-cholesta-8,13(17)-dienes (15a and 15b, resp.) via 5α- and 5β-cholesta-8,14-dienes (14a and 14b, resp.), respectively. Epimerization at C(20) of the spirosteradienes 15a and 15b occurs with increasing reaction time. Molecular-mechanics calculation of the relative stabilities of these compounds and of congeners thereof is in agreement with the observed reaction pathway.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790407
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  • 95
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    Asymmetric Synthesis of the Alkaloids mayfoline and N(1)-acetyl-N(1)-deoxymayfoline (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1085-1094 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The total syntheses of the spermidine alkaloids (-)-mayfoline (11) and (+)-N(1)-acetyl-N(1)-deoxymayfoline (12) are described. These macrocyclic lactams belong to the most interesting conjugates of the polyamine derivatives very commonly found in nature. The enantioselective syntheses were achieved through resolution of the methyl 3-amino-3-phenylpropanoate (2) by recrystallization of its (+)-L-tartrate salt. Construction of the 13-membered ring ensued through condensation, reductive ring expansion (internal bond cleavage), and finally a transamidation reaction involving a second ring expansion.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790417
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  • 96
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    Electrochemical Behaviour and Antioxidant Activity of Some Natural Polyphenols (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1147-1158 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A number of natural polyphenols (chlorogenic acid (9), cordigol (11), cordigone (12), danthrone (1), 1,5-dihydroxy-3-methoxyxanthone (2), eriosematin (7), flemichin D (8), frutinone A (6), mangiferin (4), quercetin (5), 1,3,6,7-tetrahydroxyxanthone (3) and verbascoside (10)) were investigated for their redox properties using cyclic voltammetry. The antioxidant properties of these compounds were also examined in two models, namely lipid peroxidation in rat synaptosomes and AAPH-mediated oxidation of serum albumin. Compounds with a catechol group (9, 4, 5, 3 and 10) were oxidized below 0.4 V and inhibited lipid peroxidation with IC50 values between 2 and 8 μM. Compounds having one or more isolated phenolic groups and showing an oxidation potential between 0.45 and 0.8 V (11, 12 and 8) inhibited lipid peroxidation with IC50 between 7 and 9 μM, except 2 (0.45 V), danthrone (0.96 V) and eriosematin which showed no or modest antioxidant activity. Some of the investigated compounds also protected albumin from oxidation, but no structure-activity relationship was apparent, suggesting that other factors beside redox potential influence this activity.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790422
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  • 97
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    Glycosylidene Carbenes. Part 23. Regioselective glycosidation of deoxy- and fluorodeoxy-myo-inositol derivativesDedicated to Edgar Heilbronner on the occasion of his 75th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1169-1191 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: To demonstrate the relevance of the kinetic acidity of individual OH groups for the regioselectivity of glycosylation by glycosylidene carbenes, we compared the glycosylation by 1 of the known triol 2 with the glycosylation of the diol D-3 and the fluorodiol L-4. Deoxygenation with Bu3SnH of the phenoxythiocarbonyl derivative of 5 (Scheme 1) or the carbonothioate 6 gave the racemic alcohol (±)-7. The enantiomers were separated via the allophanates 9a and 9b, and desilylated to the deoxydiols D- and L-3, respectively. The assignment of their absolute configuration is based upon the CD spectra of the bis(4-bromobenzoates) D- and L-10. The (+)-(R)-1-phenylethylcarbamates 13a and 13b (Scheme 2) were prepared from the fluoroinositol (±)-11 via (±)-4 and the silyl ether (±)-12 and separated by chromatography. The absolute configuration of 13a was established by X-ray analysis. Decarbamoylation of 13a ( → L-12) and desilylation afforded the fluorodiol L-4. The H-bonds of D-3 and L-4 in chlorinated solvents and in dioxane were studied by IR and 1H-NMR spectroscopy (Fig. 2). In both diols, HO—C(2) forms an intramolecular, bifurcated H-bond. There is an intramolecular H-bond between HO—C(6) and F in solutions of L-4 in CH2Cl2, but not in 1,4-dioxane; the solubility of L-4 in CH2Cl2 is too low to permit a meaningful glycosidation in this solvent. Glycosidation of D-3 in dioxane by the carbene derived from 1 (Scheme 3) followed by acetylation gave predominantly the pseudodisaccharides 18/19 (38%), derived from glycosidation of the axial OH group besides the pseudodisaccharides 16/17 (13%) and the epoxides 20/21 (7%), derived from protonation of the carbene by the equatorial OH group. Similarly, the reaction of L-4 with 1 (Scheme 4) led to the pseudodisaccharides 28/29 (46%) and 26/27 (14%), derived from deprotonation of the axial and equatorial OH groups, respectively. Formation of the epoxides involved deprotonation of the intramolecularly H-bonded tautomer, followed by intramolecular alkylation, elimination, and substitution (Scheme 4). The regio- and diastereoselectivities of the glycosidation correlate with the H-bonds in the starting diols.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790424
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  • 98
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    A Novel Asymmetric Benzoin Reaction Catalyzed by a Chiral Triazolium Salt. Preliminary communication (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1217-1221 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Using the chiral triazolium salt 1 as catalyst, a novel asymmetric variant of the benzoin reaction is reported. For the first time, the scope of the method is extended to a broader range of aromatic aldehydes 2, affording the acyloins 3a-h in yields of 22-72% and enantiomeric excesses up to 86%.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790427
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  • 99
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    Erratum (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1239-1239 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790429
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  • 100
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    Variation and SelectionDedicated to Professor Vladimir Prelog on the occasion of his 90th birthday (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 1260-1278 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Ninety years ago, chemical methods were used in solving biological problems. In our days, methods of evolutionary biology are going to be used in solving problems of synthetic chemistry.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790504
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