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  • gene expression
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  • 1985-1989  (5,313)
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  • 1
    Electronic Resource
    Electronic Resource
    Expression of the genes of interferons and other cytokines in normal and diseased tissues of man (1989)
    Springer
    Cellular and molecular life sciences 45 (1989), S. 526-535 
    Details
    ISSN: 1420-9071
    Keywords: Interferon ; cytokines ; interleukins ; gene expression ; transcription ; autoimmune ; disease
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Specific interferon genes are transcribed at low levels in the spleen, liver, and peripheral blood leukocytes of normal individuals in the apparent absence of virus infection while other interferon genes remain unexpressed in the same tissues. In contrast, the genes of cytokines such as IL-1, IL-6 and TNF are expressed at relatively high levels in the organs of normal individuals. The level of expression of the IL-1, IL-6 and TNF genes is markedly reduced in the livers of patients with autoimmune liver disease compared to the level of expression in the liver of normal individuals, whereas the expression of interferon genes is similar in both normal and diseased liver, suggesting that a defect in the expression of specific cytokines is associated with severe liver disease.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01990502
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  • 2
    Electronic Resource
    Electronic Resource
    The apolipoprotein multigene family: Structure, expression, evolution, and molecular genetics (1989)
    Springer
    Journal of molecular medicine 67 (1989), S. 225-237 
    Details
    ISSN: 1432-1440
    Keywords: Atherosclerosis ; Apolipoprotein ; Gene expression ; Genetics ; Evolution ; Gene duplication ; Lipid binding ; DNA polymorphism ; Hypercholesterolemia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The plasma apolipoproteins can be classified into two subgroups: the soluble apolipoproteins including apolipoprotein (apo) A-I, A-II, A-IV, C-I, C-II, C-III, and E, and the apoBs including apoB-100 and apoB-48. The soluble apolipoproteins have very similar genomic structures, each having a total of three introns at the same locations; apoA-IV is an exception in that it has lost its first intron. Using the exon/intron junctions as reference points, we can obtain an alignment of the coding regions of all the soluble apolipoprotein genes. The mature peptide regions of the genes are almost completely made up of tandem repeats of 11 codons. The part of mature peptide region encoded by exon 3 contains a common block of 33 codons, whereas the part encoded by exon 4 contains a much more variable number of internal repeats of 11 codons. On the basis of the degree of homology of the various sequences, and the pattern of the internal repeats in these genes, an evolutionary tree has been proposed for the soluble apolipoprotein genes. ApoB-100 differs considerably from the soluble apolipoproteins. It is the largest apolipoprotein containing 4536 amino acid residues. Two types of internal repeats are identified in apoB-100: amphipathic α-helical repeats and proline-containing repeats with high β-sheet content. The apoB gene contains 29 exons and 28 introns. Its evolutionary relationship to the soluble apolipoprotein genes is unclear. The 3′ end of the apoB gene contains a region of variable number of tandem 12–16-base pair repeats. We have applied the polymerase chain reaction technique to characterize this highly polymorphic locus. The same technique can be used to accurately type other variable number of tandem repeats loci. Finally, apoB-48 was shown to be the product of an RNA editing mechanism involving an intestinal mRNA that has an in-frame UAA stop codon resulting from a C→U change in the codon CAA encoding Gln-2153 in apoB-100 mRNA. Using a molecular approach to apolipoprotein synthesis, structure and genetic analysis, we have generated information important to our understanding of lipoprotein metabolism; we also uncovered unexpected experimental results that are relevant to general cell and molecular biology and molecular evolution.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01717324
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  • 3
    Electronic Resource
    Electronic Resource
    The genetic predisposition to fibrocalculous pancreatic diabetes (1989)
    Springer
    Diabetologia 32 (1989), S. 45-51 
    Details
    ISSN: 1432-0428
    Keywords: Genetics ; insulin gene ; DQβ gene ; fibrocalculous pancreatic diabetes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Fibrocalculous pancreatic diabetes (previously known as tropical pancreatic diabetes) is a rare cause of diabetes confined to countries within the tropical belt. The aetiology of fibrocalculous pancreatic diabetes is thought to be environmental although the agent(s) is unknown. We have investigated a possible genetic basis of this disease by looking for restriction fragment length polymorphisms of genes implicated in the aetiology of diabetes mellitus. Seventy-six Dravidian patients with fibrocalculous pancreatic diabetes were studied, and the restriction fragment length polymorphisms obtained compared to racially matched control subjects (n=94), patients with Type 2 (non-insulin-dependent) diabetes (n=87) and Type 1 (insulin-dependent) diabetes (n=58). No association of fibrocalculous pancreatic diabetes was found with restriction fragment length polymorphisms of the insulin receptor gene. Although no association of fibrocalculous pancreatic diabetes was found with polymorphism of the HLA DRα/DQα/DXα genes, an association was found with the Taq 1 restriction fragment length polymorphisms of the DQβ gene (DQβ T2/T6 present in 39% of patients with fibrocalculous pancreatic diabetes compared to 19% in control subjects; p=0.01; corrected p value=0.04) which is similar to that found in Type 1 but not Type 2 diabetes. An association of fibrocalculous pancreatic diabetes was also found with the hypervariable region in the 5-prime flanking region of the insulin gene; 40% of patients possessed the class 3 allele compared to 9.5% of control subjects p=0.0001; corrected p value=0.0008). In Type 2 diabetes, similar results were obtained with 33% subjects possessing the class 3 allele (p value compared to control subjects=0.0005; corrected p value=0.004). This study suggests that fibrocalculous pancreatic diabetes has a genetic component in its aetiology. Furthermore, its origin might be related to an individual with part of the genetic predisposition to diabetes (Type 1 or Type 2) who additionally has evidence of chronic calcific pancreatitis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00265403
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  • 4
    Electronic Resource
    Electronic Resource
    Population biology of two land snails (Mesomphix spp.): variation among six southern appalachian sites with differing disturbance histories (1989)
    Springer
    Oecologia 79 (1989), S. 372-382 
    Details
    ISSN: 1432-1939
    Keywords: Logging disturbance ; Land gastropods ; Ecology ; Genetics ; Population
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Ecological and genetic properties of two North American terrestrial gastropods (Mesomphix spp.) were characterized in paired control and previously logged watersheds in two North Carolina forests (Coweeta and the Great Smoky Mountains National Park) of the Southern Appalachian Biosphere Reserve Cluster. Shell growth was greater in the control sites, but density and mortality were largely independent of prior logging history and forest reserve. Based on starch gel electrophoresis data, both species showed their highest levels of genetic diversity in the Coweeta forest, the component of the reserve cluster which had the most extensive and variable history of logging disturbance. M. subplanus also exhibited higher levels of heterozygosity in logged than in control watersheds, and M. andrewsae showed over twice as many rare alleles in disturbed sites as in control sites. F-statistic analysis depicted both excess levels of homozygosity and moderate genetic differentiation among the populations, reflecting the effects of small population size and perhaps drift and inbreeding. Estimated gene flow was relatively low. These results correspond to the recent finding by Bryant et al. (1987) and others on the effects of bottlenecks, and to the contrasting history of habitat instability of the two major study forests.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00384317
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  • 5
    Electronic Resource
    Electronic Resource
    Convulsant properties of GABA antagonists and anticonvulsant properties of ethanol in selectively bred Long- and Short-Sleep mice (1989)
    Springer
    Psychopharmacology 98 (1989), S. 544-548 
    Details
    ISSN: 1432-2072
    Keywords: Ethanol ; Bicuculline ; Picrotoxin ; Seizures ; Genetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The convulsant potency of bicuculline, a GABA antagonist, was shown to be greater in Short-Sleep (SS) mice than in Long-Sleep (LS) mice. LS mice, selectively bred for lengthy ethanol-induced narcosis, had longer latencies to myoclonus and clonus following administration of bicuculline and picrotoxin than did ethanol-resistant SS mice. SS mice were also more susceptible to pentylenetetrazol-induced myoclonus, but not clonus. F1 hybrids showed bicuculline seizure sensitivity intermediate to the two parent lines. Ethanol weakly inhibited bicuculline-induced myoclonus in both LS and SS mice. Clonus was clearly antagonized by ethanol in both lines, but to a similar degree. These data provide evidence for a GABAergic role in geno-type-dependent sensitivity to ethanol.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00441957
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  • 6
    Electronic Resource
    Electronic Resource
    Cocaine produces low dose locomotor depressant effects in mice (1989)
    Springer
    Psychopharmacology 99 (1989), S. 147-150 
    Details
    ISSN: 1432-2072
    Keywords: Locomotor activity ; CNS depression ; Cocaine ; Mice ; Behavior ; Genetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Cocaine produces several behavioral effects, most notably locomotor stimulation. Biochemically, cocaine is known to inhibit reuptake at the three monoamine transporter sites, and may have highest affinity at the serotonin transporter. Serotonin augmentation has been associated with decreases in behavioral activity, but cocaine has not been reported to produce behavioral depressant effects except at high doses which cause stereotypy and disruption of behavior. This study examined the effects of relatively low doses of cocaine, in the range of 0.1–10 mg/kg, on locomotor activity in C57BL/6J and DBA/2J mice. A biphasic dose-response curve was seen for both strains. At the lowest doses, activity was depressed. As the dose of cocaine increased, activity returned to baseline, and at the highest doses, increases in locomotor activity were found. DBA/2J mice were depressed at a lower dose of cocaine than were C57BL/6J mice; however, C57BL/6J mice showed locomotor depression over a broader range of doses. Activity was maximally depressed at 0.1 mg/kg for DBA/2J mice, and maximally depressed at 0.3 mg/kg for C57BL/6J mice. Thus, low doses of cocaine are shown to produce significant decreases in locomotor activity in two strains of mice. It is postulated that these low doses of cocaine which depress locomotor activity do so via inhibition of serotonin uptake, resulting in potentiation of serotonergic activity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00442799
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  • 7
    Electronic Resource
    Electronic Resource
    Genotype-dependent effects of GABAergic agents on sedative properties of ethanol (1989)
    Springer
    Psychopharmacology 98 (1989), S. 518-523 
    Details
    ISSN: 1432-2072
    Keywords: Ethanol ; GABA ; Bicuculline ; Sedation ; Genetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Two lines of mice, selectively bred for differential sensitivity to the soporific effects of ethanol (ETOH), were administered GABAergic drugs in an effort to evaluate a role for GABA in ETOH sensitivity. ETOH sensitive Long-Sleep mice (LS) showed potentiated ETOH sedation when administered bicuculline, muscimol and aminooxyacetic acid (AOAA). ETOH-insensitive SS mice exhibited reduced ETOH sedation in the presence of the antagonists, bicuculline and picrotoxin, and potentiated sedation in the presence of muscimol and AOAA. These changes in narcosis duration were interpreted as central effects, since blood ethanol levels at waking from ETOH sedation varied with GABAergic drug treatment. Picrotoxin antagonized pentobarbital-induced nacrosis in both lines, but to a greater extent in SS mice. These and other experiments with a genetically heterogeneous stock suggest GABA involvement in genotype-dependent ETOH sensitivity, but do not support a simple role of GABA receptor involvement.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00441952
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  • 8
    Electronic Resource
    Electronic Resource
    Modification of ethanol effects by bicuculline: genotype-dependent responses and inheritance (1989)
    Springer
    Psychopharmacology 98 (1989), S. 549-555 
    Details
    ISSN: 1432-2072
    Keywords: Ethanol (ETOH) ; GABA ; Bicuculline ; Sedation ; Genetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Genetic influences on the interaction between ethanol (ETOH) and gamma-aminobutyric acid (GABA) neurotransmitter systems were eveluated with a survey of responses to coadministration of ETOH and a GABA antagonist, bicuculline, in a battery of inbred mouse strains. The selectively bred ETOH-sensitive Long-Sleep (LS) mice, the relatively ETOH-resistant Short-Sleep (SS) mice, and a genetically heterogeneous stock (GHS) were also evaluated. The effect of bicuculline on ETOH-induced sedation, hypothermia, and blood ethanol content upon recovery from sedation was assessed. Inheritance of these responses was also examined using F1 hybrids. The effect of bicuculline on ETOH-produced narcosis varied widely among stocks and included antagonism, potentiation, and no effect. Changes in ETOH-induced narcosis produced by bicuculline were accompanied by changes in blood ethanol concentrations consistent with an hypothesis of altered central nervous system sensitivity to ETOH. Knowledge of a strain's seizure susceptibility to the GABA antagonist or of its sensitivity to the hypnotic effects of ETOH were of no predictive value in estimating the outcome of coadministration studies, suggesting at least partially separate genetic influences on each phenotype. In cross-breeding studies there was commonly dominance toward a profile of bicuculline antagonism of ETOH narcosis but different patterns of dominance were observed for seizure susceptibility, again inicating separate genetic control. The results suggest considerable complexity of GABAergic involvement in genotype-dependent ETOH sensitivity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00441958
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  • 9
    Electronic Resource
    Electronic Resource
    Homology and distribution of CO dehydrogenase structural genes in carboxydotrophic bacteria (1989)
    Springer
    Archives of microbiology 152 (1989), S. 335-341 
    Details
    ISSN: 1432-072X
    Keywords: Carboxydotrophic bacteria ; Plasmids ; CO dehydrogenase subunits ; N-terminal sequences ; Oligonucleotides ; Hybridization ; Genetics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The 17 (S), 30 (M) and 87 kDa (L) subunits of CO dehydrogenases from the CO-oxidizing bacteria Pseudomonas carboxydoflava, Pseudomonas carboxydohydrogena and Pseudomonas carboxydovorans OM5 were isolated and purified. The N-terminal sequences of same subunits from different bacteria showed distinct homologies. Dot blot hybridization employing oligonucleotide probes derived from the sequences of the S-subunit of P. carboxydovorans OM5 and the M-subunit of P. carboxydohydrogena and DNA of the plasmid-containing CO-oxidizing bacteria Alcaligenes carboxydus, Azomonas B1, P. carboxydoflava, P. carboxydovorans OM2, OM4 and OM5 indicated that all genes encoding these subunits reside on plasmids. That in P. carboxydovorans OM5 CO dehydrogenase structural genes are located entirely on plasmid pHCG3 was evident from the absence of hybridization employing DNA from the cured mutant strain OM5-12. CO dehydrogenase structural genes could be identified on the chromosome of the plasmid-free bacteria Arthrobacter 11/x, Bacillus schlegelii, P. carboxydohydrogena and P. carboxydovorans OM3. There was no example of a plasmid-harboring carboxydotrophic bacterium that did not carry CO dehydrogenase structural genes on the plasmid. The N-terminal sequences of CO dehydrogenase structural genes were found to be conserved among carboxydotrophic bacteria of distinct taxonomic position, independent of the presence of plasmids. It is discussed whether this might be the consequence of horizontal gene transfer.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00425170
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  • 10
    Electronic Resource
    Electronic Resource
    The use of eye movement dysfunctions in exploring the genetic transmission of schizophrenia (1989)
    Springer
    European archives of psychiatry and clinical neuroscience 239 (1989), S. 43-48 
    Details
    ISSN: 1433-8491
    Keywords: Schizophrenia ; Eye movements ; Genetics ; Twins ; Latent trait
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Eye movement dysfunctions have been found in a large number of schizophrenic patients and in about half of their first-degree relatives. The distribution of these traits within the families of schizophrenic patients suggests a model of genetic transmission that fits an autosomal dominant model, which we have called the “genetic latent trait model.” The model, with seven parameters, was fitted to a U.S. population and the model was cross-validated on an independent Norwegian sample. Although the model does not invalidate other, more conventional solutions to the puzzle of schizophrenic transmission, such as multifactorial transmission, the latent trait model does more easily permit linkage studies and therefore will allow refutation or support from the use of molecular genetics techniques.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01739743
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  • 11
    Electronic Resource
    Electronic Resource
    Genetic and tissue-specific variation in the expression of a closely linked murine multigene family on chromosome 15 that encodes salivary and lacrimal proteins (1989)
    Springer
    Biochemical genetics 27 (1989), S. 613-637 
    Details
    ISSN: 1573-4927
    Keywords: mouse ; salivary protein ; lacrimal protein ; gene expression ; Spt locus ; multigene family
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The murine submandibular gland (SMG) produces a novel class of highly acidic salivary proteins encoded by one or more highly abundant mRNA transcripts. In inbred mice, these transcripts are encoded by members of a multigene family comprising approximately 8–12 homologues. Most, and probably all, of these homologues are clustered at a new locus near belted (bt) on chromosome 15, which we designateSpt (salivary protein). Although physically closely linked,Spt genes differ in their patterns of expression both in strains of mice and in their tissues. One gene,Spt-1, is expressed at high levels in the SMG of all inbred strains examined. This gene is also expressed at significant levels in the lacrimal gland. A second gene,Spt-2, appears to be present as a single copy in some strains and as two copies in others. This gene is expressed at high levels only in the SMG of those strains carrying two copies, andSpt-2 mRNA is not detectable in the SMG of strains carrying only one copy. In contrast toSpt-1, theSpt-2 gene is not expressed at detectable levels in the lacrimal gland.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00553636
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  • 12
    Electronic Resource
    Electronic Resource
    Genetic and tissue-specific variation in the expression of a closely linked murine multigene family on chromosome 15 that encodes salivary and lacrimal proteins (1989)
    Springer
    Biochemical genetics 27 (1989), S. 613-637 
    Details
    ISSN: 1573-4927
    Keywords: mouse ; salivary protein ; lacrimal protein ; gene expression ; Spt locus ; multigene family
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract The murine submandibular gland (SMG) produces a novel class of highly acidic salivary proteins encoded by one or more highly abundant mRNA transcripts. In inbred mice, these transcripts are encoded by members of a multigene family comprising approximately 8–12 homologues. Most, and probably all, of these homologues are clustered at a new locus near belted (bt) on chromosome 15, which we designateSpt (salivary protein). Although physically closely linked,Spt genes differ in their patterns of expression both in strains of mice and in their tissues. One gene,Spt-1, is expressed at high levels in the SMG of all inbred strains examined. This gene is also expressed at significant levels in the lacrimal gland. A second gene,Spt-2, appears to be present as a single copy in some strains and as two copies in others. This gene is expressed at high levels only in the SMG of those strains carrying two copies, andSpt-2 mRNA is not detectable in the SMG of strains carrying only one copy. In contrast toSpt-1, theSpt-2 gene is not expressed at detectable levels in the lacrimal gland.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02396156
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  • 13
    Electronic Resource
    Electronic Resource
    Regulation of human and murine complement: Comparison of 5′ structural and functional elements regulating human and murine complement factor B gene expression (1989)
    Springer
    Molecular and cellular biochemistry 89 (1989), S. 1-14 
    Details
    ISSN: 1573-4919
    Keywords: complement ; factor B ; gene expression ; interferon-ψ ; interleukin-1
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology , Medicine
    Notes: Abstract The serine protease complement factor B (Bf), an acute phase plasma protein, is a component of the alternative pathway of complement activation. Previous studies revealed that several cytokines including IFN-γ and IL-1 are involved in mediating acute phase Bf expression. To determine the molecular details of Bf expression we isolated, sequenced and characterized the 5′ flanking regions of the human and murine Bf genes. In both species the Bf transcriptional start site in liver was located 〈400 by 3′ to the polyadenylation site of the upstream C2 gene. This upstream intergenic region contained 〉65% nucleotide homology between species. Within this region, an IRS and three heat shock consensus elements were found in the murine sequence in an identical position to that of the human. To examine the functional details of Bf expression, a series of mouse and human Bf promoter - chloramphenicol acetyltransferase (CAT) chimeric gene constructs were transfected into mouse L or human HepG2 cells. Analysis of expression of these fusion gene constructs revealed that 1) cis-acting DNA sequences identified, at least in part, in the 3′ untranslated region of the C2 gene (within the 400 by upstream of the Bf cap site) mediate responsiveness to IL-1 and IFN-γ, 2) the responsiveness to each mediator appears to be conferred by separate upstream regions similar in position and homologous in man and mouse, and 3) the IL-1 responsive region in both species appears to have the characteristics of an enhancer element. The results of this analysis suggest a selective pressure to conserve the intergenic sequence between C2 and Bf genes and that further studies of these sequences will be useful in elucidating mechanisms controlling the acute phase response.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00228274
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  • 14
    Electronic Resource
    Electronic Resource
    Differential early activation of defense-related genes in elicitor-treated parsley cells (1989)
    Springer
    Plant molecular biology 12 (1989), S. 227-234 
    Details
    ISSN: 1573-5028
    Keywords: differential cDNA screening ; gene expression ; hybrid-select in vitro translation ; nuclear run-off transcription ; RNA blot hybridization
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract A cDNA library from cultured parsley (Petroselinum crispum) cells was differentially screened using labeled run-off transcripts derived from nucleic of elicitor-treated and untreated cells. This resulted in the isolation of 18 independent cDNA families representing putative defense-related genes. All genes are rapidly and transiently activated after elicitor application, but the time courses of transcriptional activity exhibit considerable variations, indicating differences in the mechanisms of gene regulation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00020507
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  • 15
    Electronic Resource
    Electronic Resource
    A unified matrix hypothesis of DNA-directed morphogenesis, protodynamism and growth control (1989)
    Springer
    Bioscience reports 9 (1989), S. 157-188 
    Details
    ISSN: 1573-4935
    Keywords: matrix hypothesis ; morphogenesis ; protodynamics ; growth control ; DNA ; genome organisation ; gene expression ; gene regulation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract A theoretical concept is proposed, in order to explain some enigmatic aspects of cellular and molecular biology of eukaryotic organisms. Among these are the C-value paradox of DNA redundancy, the correlation of DNA content and cell size, the disruption of genes at DNA level, the “Chromosome field” data of Lima de Faria (Hereditas 93∶1, 1980), the “quantal mitosis” proposition of Holtzeret al. (Curr. Top. Dev. Biol. 7∶229 1972), the inheritance of morphological patterns, the relations of DNA and chromosome organisation to cellular structure and function, the molecular basis of speciation, etc. The basic proposition of the “Unified Matrix Hypothesis” is that the nuclear DNA has a direct morphogenic function, in addition to its coding function in protein synthesis. This additional genetic information is thought to be largely contained in the non-protein coding transcribed DNA, and in the untranscribed part of the genome.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01115994
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  • 16
    Electronic Resource
    Electronic Resource
    Expression of an active spinach acyl carrier protein-I/protein-A gene fusion (1989)
    Springer
    Plant molecular biology 12 (1989), S. 95-104 
    Details
    ISSN: 1573-5028
    Keywords: acyl carrier protein ; fatty acid synthesis ; gene expression ; gene fusion ; protein A ; spinach
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract A synthetic gene encoding spinach acyl carrier protein I (ACP-I) was fused to a gene encoding the Fc-binding portion of staphylococcal protein A. This gene fusion, under the control of the λPR promoter, was expressed at high levels in Escherichia coli producing a 42 kDa fusion protein. This fusion protein was phosphopantethenylated in E. coli. In vitro the ACP portion of the fusion protein was able to participate in acyl ACP synthetase reactions, plant malonyl-CoA:ACP transacylase (MCT) reactions, and plant fatty acid synthetase (FAS) reactions. Inhibitory effects of high ACP concentrations on in vitro plant FAS were observed with the unfused ACP-1 but not with the fusion protein. As with unfused ACP-I, the fusion protein was a poor substrate for E. coli FAS reactions. When injected into rabbits, the fusion protein was also able to generate antiserum to spinach ACP-I.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00017452
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  • 17
    Electronic Resource
    Electronic Resource
    cDNA sequence and differential expression of the gene encoding the glutamine synthetase γ polypeptide ofPhaseolus vulgaris L. (1989)
    Springer
    Plant molecular biology 12 (1989), S. 553-565 
    Details
    ISSN: 1573-5028
    Keywords: cDNA sequence ; gene expression ; glutamine synthetase ; legume-Rhizobium symbiosis ; nitrogen metabolism ; Phaseolus vulgaris L.
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract We report the sequence of an essentially full-length glutamine synthetase (GS) cDNA clone (pcGS-γ1) isolated from a root nodule library ofPhaseolus vulgaris L. The polypeptide encoded by this cDNA has been producedin vitro by transcription/translation and shown to co-migrate on two-dimensional gels with the previously identified major cytosolic GS polypeptide (γ) of nodules. Two previously identified GS cDNA clones, pR-2 and pR-1 (see Gebhardtet al., EMBO J 5: 1429–1435, 1986) have similarly been shown to encode the α and β cytosolic GS polypeptides respectively. An RNase protection technique has been used to analyse specifically and quantitatively the abundance of mRNA related to these three GS cDNAs and to the cDNA (pcGS-δ1) encoding the chloroplast-located GS, during nodulation. Differences in the abundances of these mRNAs at different times suggest that they are not coordinately regulated. Moreover, using this technique mRNA specifically related to pcGS-γ1 was found at high levels in nodules but not in roots or leaves. Surprisingly the expression of this gene is not nodule-specific as previously suggested, as its mRNA was also detected, but at lower levels, in stems, petioles and in green cotyledons. By comparison, mRNA related to a leghaemoglobin gene was detected only in nodules. Comparisons of the relative abundances of the pcGS-γ1 mRNA and the γ polypeptide in different organs and at different stages during nodulation, suggest that the appearance of the γ polypeptide is largely under transcriptional control.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00036969
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  • 18
    Electronic Resource
    Electronic Resource
    Antisense RNA inhibition of β-glucuronidase gene expression in transgenic tobacco plants (1989)
    Springer
    Plant molecular biology 13 (1989), S. 399-409 
    Details
    ISSN: 1573-5028
    Keywords: antisense RNA ; β-glucuronidase ; tobacco ; transgenic plants ; gene expression
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract Antisense RNA was used to specifically inhibit the expression of a GUS gene introduced in a transgenic plant. A tobacco transformant containing a single intact copy of the GUS gene and showing relatively high constitutive levels of GUS activity (GUS+) was re-transformed with an Agrobacterium Ti-derived binary vector containing an antisense version of this reporter gene. The sense and antisense GUS genes were each under the regulation of the CaMV 35S promoter. Re-transformed plants contained 1–5 copies of the antisense construct and all showed a greater than 90% reduction in GUS activity relative to the original GUS+ plant. This reduction in GUS activity correlated closely with the levels of GUS enzyme and steady state GUS mRNA observed in these plants. The relatively low levels of sense and antisense GUS transcripts found in the re-transformed plants may indicate a rapid degradation of the RNA:RNA duplex in the cell.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00015552
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  • 19
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    Electronic Resource
    Involvement of Rhizobium leguminosarum nodulation genes in gene expression in pea root hairs (1989)
    Springer
    Plant molecular biology 12 (1989), S. 157-167 
    Details
    ISSN: 1573-5028
    Keywords: deformation factor ; gene expression ; pea ; Rhizobium leguminosarum ; root hairs
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The mRNA population in pea root hairs was characterized by means of in vitro translation of total root hair RNA followed by 2-dimensional gel electrophoresis of the translation products. Root hairs contain several mRNAs not detectable in total RNA preparations from roots. Most of these root hair-specific mRNAs occur in elongating root hairs at higher levels than in mature root hairs. The expression of some genes in pea root hairs is typically affected by inoculation with Rhizobium leguminosarum. One gene, encoding RH-42, is specifically induced while the expression of another gene, encoding RH-44, is markedly enhanced. Using R. leguminosarum mutants it was shown that the nodC gene is required for the induction and enhancement of expression of the RH-42 and RH-44 genes, respectively, while the Rhizobium chromosomal gene pss1, involved in exopolysaccharide synthesis, is not essential. After induction of the nod genes with apigenin the bacteria excrete into the culture medium a factor that causes root hair deformation. This deformation factor stimulates the expression of the RH-44 gene but does not induce the expression of the gene encoding RH-42.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00020501
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  • 20
    Electronic Resource
    Electronic Resource
    Phytochrome control of multiple transcripts of the phytochrome gene in Pisum sativum (1989)
    Springer
    Plant molecular biology 12 (1989), S. 295-299 
    Details
    ISSN: 1573-5028
    Keywords: gene expression ; multiple transcripts ; phytochrome ; Pisum sativum ; red/far-red reversible effect
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The reversible effect of red and far-red light on the level of two RNA transcripts of the single-copy phytochrome gene in pea was investigated using the primer extension assay. In dark-grown seedlings, a brief irradiation with red light markedly reduced the level of one of the phytochrome transcripts, RNA1. This red light effect was reversed by subsequent irradiation with far-red light. The other phytochrome transcript, RNA2, was only slightly influenced by light. In light-grown seedlings, a brief irradiation with far-red light increased the content of both RNA1 and RNA2 when the seedlings were transferred from light to darkness. This far-red light effect was reversible by subsequent red light irradiation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00043206
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  • 21
    Electronic Resource
    Electronic Resource
    Structure and expression of the maize gene encoding the phosphoenolpyruvate carboxylase isozyme involved in C4 photosynthesis (1989)
    Springer
    Plant molecular biology 12 (1989), S. 579-589 
    Details
    ISSN: 1573-5028
    Keywords: C4 photosynthesis ; gene structure ; gene expression ; genetic variation ; silent substitution ; Zea mays
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract We have determined the structure of the maize (Zea mays L. subsp.mays line B73) nuclear gene encoding the phosphoenolpyruvate (PEP) carboxylase isozyme involved in C4 photosynthesis. The gene is 5.3 kb long and has ten exons that range in size from 85 to 999 bp. The nine introns vary from 97 to 872 bp. The sequence of 663 bp of 5′-flanking and 205 bp of 3′-flanking DNA is reported along with the entire gene sequence. Several short repetitive sequences were found in the 5′-flanking DNA that have characteristics similar to elements important in the light regulation of pea genes encoding the small subunit of ribulose 1,5-bisphosphate carboxylase. In addition, some 5′-flanking sequence similarities were found in a comparison with other light-regulated genes from maize and wheat. The level of DNA sequence variation among different PEP carboxylase alleles is similar to the allelic variation observed for several other maize nuclear genes. The data suggest modern maize variaties have retained much of the genetic variation present in their ancestral forms. Finally, accumulation of transcripts encoding the PEP carboxylase isozyme involved in C4 photosynthesis is quite high in several structures besides leaves, including inner leaf sheaths, tassels and husks. This indicates that expression of this gene is not leaf-specific and may not necessarily be coupled to the development of Kranz anatomy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00036971
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  • 22
    Electronic Resource
    Electronic Resource
    The bifunctional α-amylase/subtilisin inhibitor of barley: nucleotide sequence and patterns of seed-specific expression (1989)
    Springer
    Plant molecular biology 12 (1989), S. 673-682 
    Details
    ISSN: 1573-5028
    Keywords: amylase inhibitor ; barley ; cDNA sequence ; gene expression ; hormonal regulation ; protease inhibitor
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract We have cloned and sequenced a full-length cDNA from barley (Hordeum vulgare L.) seeds encoding the bifunctional α-amylase/subtilisin inhibitor (BASI). The nucleotide sequence predicts an open reading frame coding for a protein of 203 amino acids. The first 22 amino acids exhibit the sequence characteristic of a signal peptide, as found in several other plant protease inhibitors. Northern blot hybridization experiments indicate that BASI mRNA accumulation is strictly tissue-specific and is developmentally programmed. BASI mRNA transcripts were only identified in 1) developing starchy endosperm tissue from 14 days after flowering and 2) aleurone tissue of germinating seeds. In this latter tissue, BASI mRNA accumulation is enhanced by abscisic acid and abolished by gibberellic acid. Expression of BASI mRNA was also studied in the lys 3a high-lysine barley mutants Risø No. 1508 and Piggy. These high-lysine barleys show 2–4-fold higher levels as well as prolonged accumulation of BASI mRNA compared to the normal motherline Bomi. This correlates with the increased deposition of BASI protein in lys 3a barley mutants. Genomic blot analysis of barley DNA suggests that there are one or two BASI structural genes per haploid genome. Possible roles of BASI as part of a defence mechanism against precocious germination and pathogens are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00044158
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  • 23
    Electronic Resource
    Electronic Resource
    Effects of cadmium on gene expression in cadmium-tolerant and cadmium-sensitiveDatura innoxia cells (1989)
    Springer
    Plant molecular biology 12 (1989), S. 487-497 
    Details
    ISSN: 1573-5028
    Keywords: cadmium ; Datura innoxia ; gene expression ; heat shock ; tolerance
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The effect of Cd on gene expression in suspension cultures of twoDatura innoxia cell lines with differing Cd tolerance was studied.In vivo labeling experiments using [3H] leucine showed that Cd induced the synthesis of a similar range of proteins in both cell lines at a concentration which will kill the sensitive but not the tolerant cells. Corresponding changes in levels of translatable mRNA were also observed. The induction of the synthesis of proteins by Cd was transient since Cd-tolerant cells growing continuously in 250 μM CdCl2 contained a similar set ofin vitro translation products to cells growing in the absence of Cd. Although Cd had a similar effect on gene expression in both cell lines, Cd-tolerant cells possess two abundant mRNAs which are constitutively produced. These mRNAs encode proteins of low molecular weight (about 11 kDa) and are either absent or present at a low level in Cd-sensitive cells. The functions of these proteins are not known but they may be involved in the tolerance mechanism. Two-dimensional gel electrophoresis ofin vitro translation products showed that many of the Cd-induced proteins are also induced by heat shock. A 42°C heat shock resulted in agreater range and more intense induction of translatable mRNAs than 4 h exposure to 250 μM CdCl2. However a subset of mRNAs were induced specifically by Cd while other mRNAs were heat shock-specific. There was no difference in the ability of the two cell lines to tolerate heat shock. This was also reflected by the same pattern of major proteins induced by heat shock in the two cell lines.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00036963
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  • 24
    Electronic Resource
    Electronic Resource
    Expression of Anabaena ferredoxin genes in Escherichia coli (1989)
    Springer
    Plant molecular biology 12 (1989), S. 667-672 
    Details
    ISSN: 1573-5028
    Keywords: ferredoxin ; gene expression ; heterocyst ; Anabaena 7120 ; Escherichia coli
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The genes for ferredoxin from heterocysts (fdx H) and vegetative cells (pet F) of Anabaena sp. strain 7120 were subcloned into plasmid pUC 18/19. Both genes were expressed in Escherichia coli at high levels (≈10% of total protein). Pet F could be expressed from its own promoter. The ferredoxins were correctly assembled to the holoprotein. Heterocyst ferredoxin was purified from E. coli extracts on a large scale. Its biochemical and biophysical properties were identical to those of the authentic ferredoxin, isolated from Anabaena heterocysts.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00044157
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  • 25
    Electronic Resource
    Electronic Resource
    Isolation, characterization and sequence analysis of a full-length cDNA clone encoding NADH-dependent hydroxypyruvate reductase from cucumber (1989)
    Springer
    Plant molecular biology 13 (1989), S. 139-150 
    Details
    ISSN: 1573-5028
    Keywords: cDNA ; gene expression ; hydroxypyruvate reductase ; light regulation ; peroxisomal enzyme
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract A full-length cDNA encoding NADH-dependent hydroxypyruvate reductase (HPR), a photorespiratory enzyme localized in leaf peroxisomes, was isolated from a λgt11 cDNA library made by reverse transcription of poly(A)+ RNA from cucumber cotyledons. In vitro transcription and translation of this clone yielded a major polypeptide which was identical in size, 43 kDA, to the product of in vitro translation of cotyledonary poly(A)+ RNA and subsequent immunoprecipitation with HPR antiserum. Escherichia coli cultures transformed with a plasmid construct containing the cDNA insert were induced to express HPR enzyme activity. RNA blot analysis showed that HPR transcript levels rise significantly in the first eight days of light-grown seedling development. This closely resembles the pattern seen for HPR-specific translatable mRNA. DNA blot analysis indicated that a single HPR gene is likely present per haploid genome. Nucleotide sequence analysis revealed an open reading frame of 1146 bases which encodes a polypeptide with a calculated molecular weight of 41.7 kDa. The derived amino acid sequence from this open reading frame is 26% identical and 50% similar to the amino acid sequence of the E. coli enzyme phosphoglycerate dehydrogenase, which catalyzes a similar reaction and functions in a related pathway. Statistical analyses show that this similarity is significant (z〉10). The derived amino acid sequence for HPR also contains the characteristics of an NAD-binding domain.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00016133
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  • 26
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    Electronic Resource
    Genetical control and linkage relationships of isozyme markers in sugar beet (B. vulgaris L.) (1989)
    Springer
    Theoretical and applied genetics 78 (1989), S. 97-104 
    Details
    ISSN: 1432-2242
    Keywords: Beta vulgaris ; Sugar beet ; Isozymes ; Genetics ; Linkage
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Five isozyme systems were genetically investigated. The different separation techniques, the developmental expression and the use as marker system in sugar beet genetics and breeding is discussed. Isocitrate dehydrogenase was controlled by two genes. The gene products form inter- as well as intralocus dimers, even with the gene products of the Icd gene in B. procumbens and B. patellaris. Adenylate kinase was controlled by one gene. Three different allelic forms were detected, which were active as monomeric proteins. Glucose phosphate isomerase showed two zones of activity. One zone was polymorphic. Three allelic variants, active as dimers, were found. Phosphoglucomutase also showed two major zones of activity. One zone was polymorphic and coded for monomeric enzymes. Two allelic forms were found in the accessions studied. The cathodal peroxidase system was controlled by two independent genes, of which only one was polymorphic. The gene products are active as monomers. Linkage was found between red hypocotyl color (R) and Icd 2. Pgm 1, Gpi 2, Ak 1 and the Icd 2-R linkage group segregated independently.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00299761
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  • 27
    Electronic Resource
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    Optimising visual selection in early clonal generations of potato based on genetic and economic considerations (1989)
    Springer
    Theoretical and applied genetics 78 (1989), S. 665-671 
    Details
    ISSN: 1432-2242
    Keywords: Solanum tuberosum ; Genetics ; Breeding ; Plant appearance ; Economy
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary In 1985, 1986 and 1987, 600 clones were visually assessed at harvest on plant appearance. The clones were harvested 80 days after planting in the first year, in the following years after approximately 80 days as well as after 145 days. The correlation coefficients between years and between harvest times were low to medium. Simulating different selection intensities using the performance of these 600 clones in two successive years, the relation between selection pressure in the first year and the retained proportion of well performing clones in the second year was described. Including the costs of testing, the most economic selection procedure was calculated. This procedure consisted in testing 1,579 first-year clones and 499 second-year clones for every 100 third-year clones required. The optimal period of the main evaluation in the second clonal year is at ware potato harvest time. This selection procedure also provides good selection possibilities for underwater weight and foliage maturity.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00262562
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  • 28
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    A comparison of muscle precursor replication in crush-injured skeletal muscle of Swiss and BALBc mice (1989)
    Springer
    Cell & tissue research 255 (1989), S. 385-391 
    Details
    ISSN: 1432-0878
    Keywords: Myogenesis ; Muscle regeneration ; Genetics ; Autoradiography ; Tritiated thymidine ; Mouse (Swiss;BALBc)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Notes: Summary Muscle precursor replication in Swiss mice, in which muscle regeneration is exceptionally vigorous, was compared with previous data for regeneration in BALBc mice. The tibialis anterior muscles of 23 male and 15 female inbred Swiss SJL/J mice were crush injured, and tritiated thymidine injected into mice at various times after injury to label replicating muscle precursors. Lesion samples were taken 10 days after injury, processed for autoradiography, and grain counts of myotube nuclei analysed. Muscle regeneration was more vigorous in male compared with female Swiss mice, and in both was strikingly greater than that in BALBc mice in which there was extensive fibrous connective tissue throughout the lesions. Autoradiographic analysis showed that muscle precursor replication started at 24 hours in Swiss mice, 6 hours earlier than the onset at 30 hours in BALBc mice. Muscle precursor replication appeared to be more active 96 hours after injury in female Swiss compared with male BALBc and male Swiss mice respectively, although numbers of precursor cells replicating at other times were similar. It is not known whether the slight difference in onset of muscle precursor replication can alone account for the more complete muscle regeneration seen in Swiss mice. Similar studies were carried out in 11 male and 10 female F1 hybrid (SJL/J x BALBc) mice. Analysis of labelled myotube nuclei showed that muscle precursors did not synthesise DNA prior to 30 hours after injury, and regeneration resembled that of the parental BALBc strain.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00224122
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  • 29
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    Changes in gene expression in the rat brain induced by Zajdela's ascites hepatoma (1989)
    Springer
    Bulletin of experimental biology and medicine 108 (1989), S. 999-1001 
    Details
    ISSN: 1573-8221
    Keywords: brain ; gene expression ; mRNA ; transplantable hepatomas
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Medicine
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00839794
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  • 30
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    Neurons containing cholecystokinin mRNA in the mammillary region: ontogeny and adult distribution in the rat (1989)
    Springer
    Cellular and molecular neurobiology 9 (1989), S. 281-294 
    Details
    ISSN: 1573-6830
    Keywords: cholecystokinin ; mammillary region ; development ; gene expression ; hybridization histochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary 1. The ontogeny and adult distribution of neurons containing cholecystokinin (CCK) mRNA in the premammillary and mammillary nuclei and supramammillary region of the rat brain were studied using hybridization histochemistry. 2. The earliest detection of CCK mRNA in the mammillary region was on E14, followed by a marked increase in transcript levels during the next 4 days, a time during which neurons in this region still divide. During the first 2 weeks of life, few changes in the levels of CCK transcripts were seen, and an adult-like pattern of expression was seen on the twenty-first day of life. 3. Low levels of transcripts were present in numerous neurons located in all divisions of the medial nucleus and in the posterior nucleus known to project ipsilaterally to the anteroventral and anteromedial thalamic nuclei. In contrast, none of the neurons in the lateral nucleus (projecting bilaterally to the anterodorsal thalamic nucleus) had detectable transcripts. 4. Many neurons in the supramammillary nucleus had low, moderate, or high levels of transcripts. Some nearby nuclei (such as the dorsal premammillary nucleus) had smaller numbers of neurons with low levels of CCK mRNA, whereas others (such as the ventral premammillary nucleus) had none.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00713035
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    Tryptophan auxotrophic mutants in Aspergillus niger: Inactivation of the trpC gene by cotransformation mutagenesis (1989)
    Springer
    Molecular genetics and genomics 219 (1989), S. 282-288 
    Details
    ISSN: 1617-4623
    Keywords: Aspergillus ; Genetics ; Transformation ; trpC lacZ gene fusion ; Gene replacement
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Summary Aspergillus niger tryptophan auxotrophic mutants have been isolated after UV irradiation of conidiospores. The mutants belong to two different complementation groups, trpA and trpB, which complement each other in heterokaryons. Neither of the mutations could be complemented with the cloned A. niger trpC gene. To obtain A. niger trpC mutants in a direct way, gene inactivation by cotransformation was performed. For this purpose an in-frame gene fusion between the A. niger trpC and Escherichia coli lacZ genes was constructed and shown to be functionally expressed after introduction into A. niger by cotransformation with the pyrA gene as selective marker. Among the β-galactosidase expressing cotransformants, obtained with either circular or linearized vectors, no trpC mutants were detected, even after enrichment. Such mutants, however, could be obtained by cotransformation of A. niger with specific fragments of the fusion gene. Biochemical analysis of the cotransformants indicated that in nearly all cases the fusion gene had replaced the wild-type trpC gene. Genetic analysis showed that the trpC mutation is not linked to any of the A. niger loci described so far. The trpC mutants can be complemented by the cloned A. niger trpC gene as well as by the A. nidulans trpC gene.
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    URL: http://dx.doi.org/10.1007/BF00261189
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  • 32
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    Functional mapping of the activity of the R region in the human T-cell leukemia virus type I long terminal repeat to increase gene expression (1989)
    Springer
    Virus genes 2 (1989), S. 147-155 
    Details
    ISSN: 1572-994X
    Keywords: BAL31 nuclease ; CAT assay ; gene expression ; HTLV-I ; R region ; 5′ untranslated sequence
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We previously demonstrated the activity of the R fragment in the long terminal repeat of human T-cell leukemia virus type I for elevation of the level of gene expression. In this study, the fragment was deleted with BAL31 nuclease to determine its functional domain. Series of the shortened R fragments were linked to the simian virus 40 promoter unit, which regulated expression of a reporter gene. Examination with the R fragments deleted from the 5′ and 3′ ends showed that borders of the functional domain were mapped within nucleotide positions 458 to 473 for the 5′ end and nucleotide positions 559 to 594 for the 3′ end, respectively. Thus we conclude that a 136-base-pair fragment corresponding to the second half of the R region was sufficient to allow elevation of the level of gene expression.
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    URL: http://dx.doi.org/10.1007/BF00315258
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    Masthead (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989) 
    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.19890720101
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  • 34
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    The Conformation of Cycloartenol Investigated by NMR and Molecular Mechanics (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 1-13 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cycloartenol (4), a natural plant sterol, was shown to be an effective membrane reinforcer; this was attributed to its conformation. We now present a conformational analysis of 4 by molecular modeling and NMR. Molecular modeling suggests that two conformations I and II coexist, differing mainly at the level of ring C, and of nearly equal energy, I and II each having ring A and B in a chair and half-chair conformation, respectively, with ring C 1,3-diplanar in I (solid-state structure as determined by X-ray crystallography) and in chair conformation in II. A complete assignment of the 1H- and 13C-NMR spectra of 4 and the entire coupling network in rings A and B is determined by various modern NMR techniques. The conformation of rings A and B thus determined is in agreement with conformations I and II. Low-temperature NMR experiments show a fast equilibrium between two conformations, presumably I and II. It is concluded, therefore, that the cyclopropane ring of 4 produces a flexibility at the level of ring C which may be important for the membrane properties.
    Additional Material: 8 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720102
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  • 35
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    Palladium(0)-Catalyzed Cyclizations of Simple 1-Aryl-1,7-octadien-3-yl Acetates. Preliminary communicationPresented (W.O.) at the ‘3e Congrès national de la Société Française de Chimie’, Nice, September 5, 1988. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 14-16 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dienyl acetates 2 lacking a geminal disulfone or a malonate group cyclize selectively to (E)-l-methylidene-2-styrylcyclopentanes 4 in the presence of 7 mol-% of [Pd(PPh3)4].
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720103
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  • 36
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    Über den Einfluss des Akzeptor-Teilchromophors bei Dimethin-merocyanin-Farbstoffen auf das Aggregationsverhalten in wässriger Lösung (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 17-28 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On the Influence of the Acceptor Part of the Chromophor of Dimethinemerocyanine Dyes upon the Aggregation Tendency in Aqueous SolutionA series of novel long-chain alkyl-dimethinemerocyanine dyes containing sulfonate groups is synthesized in good yield and their aggregation tendency in H2O and in organic solvent/H2O mixtures investigated. The merocyanine dyes 11 and 15 only exhibit an intense, red-shifted absorption band due to J-aggregation in H2O without addition of salt. The influence of cationic and anionic tensides and other compounds as urea, glucose, and polysaccharides upon the J-aggregation tendency is investigated.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720104
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  • 37
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    Generation and Trapping of TriafulveneFulvene, Fulvalenes, Part 55; Part 54: [1].Short communication: [2]. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 29-40 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Substituted methylidenecyclopropanes 12a-d, being easily available from 1,1-dibromo-2-(phenylthio)-cyclopropane (9a), are attractive precursors of triafulvene (2-methylidene-1-cyclopropene; 1). Both the sulfoxide 12b and the sulfone 12c react with an excess of alkoxides (t-BuOK and NaOMe) to give 12e and 12f, respectively, while the sulfinyl group of 12b may be replaced by the PhCH2S substituent in the presence of PhCH2SH/t-BuOK. These reactions (Scheme 4) may be explained by assuming 1 as a reactive intermediate, although an alternative sequence including carbene 20 (Scheme 6) is not completely ruled out. D-labelling experiments (Scheme 5) do not give conclusive evidence due to D scrambling, but deprotonation/methylation sequences show that H—C(2) of 12a-c is the most acidic proton. Final evidence for 1 results from the reaction of 12d with cyclopentadienide (Scheme 7): the reaction of 1 with cyclopentadiene produces the expected [4 + 2]-cycloaddition product 23, while some mechanistic insight results from the sequence 12d → 24 → 25.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720105
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  • 38
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    A Nonconcerted Intramolecular Diels-Alder Reaction of Chiral Allenic-Acid Derivatives (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 59-64 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The reaction between the chiral allenic acid (+)-(S)-1 and the carbodiimides 2a-d and the keten-imine 6 gives, under mild conditions, the tricyclic compounds 3-5, 7, and 8. Low diastereoselectivity and a partial loss of optical activity are observed. A stepwise mechanistic pathway via a biradical intermediate is postulated.
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    URL: http://dx.doi.org/10.1002/hlca.19890720108
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  • 39
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    Konkurrenz von Endoperoxid- und Hydroperoxid-Bildung bei der Umsetzung von Singulett-Sauerstoff mit cyclischen, konjugierten Dienen. Teil I (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 51-58 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Competition of Endoperoxide and Hydroperoxide Formation in the Reaction of Singlet Oxygen with Cyclic, Conjugated DienesRose-bengal-sensitized photooxygenation of (-)-(R)-α-phellandrene (1) in MeOH at room temperature yielded a complex mixture of products, contrary to previous reports describing cis-(3S, 6R)-epidioxy-p-menthene (2) and trans-(3R, 6S)-epidioxy-p-menthene (3) as the only products. The mixture was separated by prep. HPLC (silica gel, pentane/Et2O 9:1). Besides the known endoperoxides 2 (yield 39%) and 3 (26%), all those hydroper-oxides, which can be deduced from an ene reaction of 1O2 with 1, were isolated, i.e. 4β-p-mentha-2,5-dien-1β-yl hydroperoxide (4) (14%), 4β-p-mentha-2,5-dien-1α-yl hydroperoxide (5) (9%), (2R, 4R)-p-mentha-1(7), 5-dien-2-yl hydroperoxide (6) (2,1%), (2S, 4R)-p-mentha-1(7),5-dien-2-yl hydroperoxide (7) (1,5%) and (1R)-p-mentha-3,6-dien-yl hydroperoxide (8; 1,5%; Scheme 1). Furthermore, the constant cis/trans ratio for all diastereoisomeric pairs (2/2, 4/2, 6/2) was striking. With the help of the two possible conformers 1a and 1b of the starting material a model of a common first step for endoperoxide as well as for hydroperoxide formation is developed. A photooxygenation at -50° supports this model. The absolute value of the cis/trans ratio changes in the same way for the endoperoxides and the hydroperoxides.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720107
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  • 40
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    Versuche zur Synthese von Calicen aus trisubstituierten Cyclopropanen und Cyclopentenon56. Mitt. über Fulvene, Fulvalene; 55. Mitt. [1]: Kurzmitt. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 41-50 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Attempted Synthesis of Calicene from Trisubstitued Cyclopropanes and CyclopentenoneThe Li carbenoids 4, prepared by treatment of substituted 1,1-dihalocyclopropanes with BuLi, are reacted with cyclopent-2-enone under thermodynamic and kinetic control (Scheme 1). In general, the latter procedure gives better yields of cyclopropylcyclopentenols 5a-e, but the reaction seems to be controlled mainly by the steric and electronic properties of the substituent Y. So, with 4b and 4e, the main reaction is the attack of the carbenoid at C(1) of cyclopent-2-enone, while 4a (Y = PhS) predominantly deprotonates the ketone (Scheme 4). Whereas 5d and 5e can easily be converted to the dihydrocalicenes 6d and 6e (Scheme 6), the attempted elimination of H2O from 5a-c leads to the rearranged products 13-2 due to the opening of the cyclopropane ring (Scheme 5). Finally, the generation of the parent compound 2 from the silylated precursor 6d is attempted: treatment with MeO- gives the addition products 18A/18B, while the reaction with Br2 provides 19 by a bromination/dehydrobromination sequence (Scheme 7).
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    URL: http://dx.doi.org/10.1002/hlca.19890720106
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  • 41
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    Locoselective [4 + 2] Cycloadditions of Vinylindoles with Inverse Electron Demand: A new access of indolyl-substituted and annellated pyridazinesDedicated to Prof. Dr. C. H. Brieskorn (Würzburg, FRG) on the occasion of his 75th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 65-72 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-Vinylindole (1a) and its donor- and acceptor-substituted (E)-derivatives 1b-e react highly locoselectively with dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate (3) to form the novel (indol-2-yl)-1,4-dihydropyridazines 4a and 7 as well as the heterocyclic annellated pyridazines 4b, 5, and 6. The reactions of the structurally related 3-vinylindoles 2a-e with 3 also gave rise to new indol-3-ylpyridazines 8, 9, and 10. The locoselectivities of these Diels-Alder reactions were controlled mainly by steric effects.
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    URL: http://dx.doi.org/10.1002/hlca.19890720109
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  • 42
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    Photochemistry of Thiophen-2(5H)-onesDedicated to Prof. Dr. O. E. Polansky on the occasion of his 70th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 83-92 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Mechanistic evidence for the light-induced ring opening of thiophen-2(5H)-ones 1 in alcohols affording α, β-unsaturated mercapto esters 2 is presented. Regio-and stereochemical aspects of the ring closure of alkenylthio (type 3) radicals 15 and 17 to S-heterocycles 16 and 18, of 3-thiahex-5-enyl radicals 4 to (tetrahydrothien-3-yl)methyl radicals 6 and of (2,3-dihydrothien-3-yl)methyl radicals 30 (type 7, but-3-enyl radicals) to cyclopropane-methyl radicals 29 are discussed. Irradiation (λ 350 nm) of 1 in cyclohexane in the presence of 2,3-dimethylbut-2-ene affords [2 + 2] cycloadducts 14 albeit in very low yields.
    Additional Material: 1 Tab.
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  • 43
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    Electronic and Molecular Structure of the C8H10+· Valence Isomers 1,3,5-Cyclooctatriene+· and Bicyclo[4.2.0]octa-2,4-diene+· from their Electronic absorption Spectra in Freon (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 73-82 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The molecular cations of 1,3,5-cyclooctatriene (COT+·) and bicyclo[4.2.0]octa-2,4-diene (BCO+·) can be observed intact in γ-irradiated Freon glasses, as opposed to Ar matrices where ionization is accompanied by extensive rearrangements. This proves the superiority of the Freon-glass method for the generation of metastable primary cations. The electronic absorption (EA) spectra reveal a) that a previous analysis of the BCO+· electronic structure on the basis of the ultraviolet photoelectron (UP( spectrum of BCO was incomplete, and b) that COT undergoes planarization upon ionization, in accord with qualitative expectations and MNDO calculations. A previously proposed LCBO model was used to assess the influence of the above geometry change on the electronic structure of COT+·.
    Additional Material: 2 Ill.
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  • 44
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    Cyclization Studies with N-Mannich bases of 2-substituted indoles (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 93-100 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the indoles 7, 15, 16 with a 3-methoxyphenyl group, attached via an α-side chain of 1,2,or 3 CH2 units, is reported. These compounds, after appropriate protection at C(3), were transformed into the N-[(dimethylamino)methyl]indoles 22, 23, and 24, respectively. When treated with AcCl, these N-Mannich bases gave, in two cases, stable N-(chloromethyl)indoles 25 and 26. In the presence of SnCl4, ring closure occurred via electrophilic attack of 1-methylideneindolium ions on the methoxyphenyl group. Formation of seven-membered rings (→ 27, 28) and eight-membered rings (→ 29) was found to be a favorable process. Cyclization to six-membered rings did not occur within this series.
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    URL: http://dx.doi.org/10.1002/hlca.19890720112
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  • 45
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    Template-Dependent Incorporation of Spin-Labeled Thymidine Analogs into Viral DNA (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 110-116 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of novel pppUd analogs substituted at position C(5) with tethered nitroxide radicals is reported. It is shown that these analogs can serve as good substrates for E. coli DNA polymerase (Pol I) and T-4 DNA polymerase using lambda-phage DNA as template. The template-dependent incorporation of the substrates was established by radio-labeling and ESR experiments.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720114
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  • 46
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    Stereoselektive Synthesen von Taxan-Derivaten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 101-109 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Stereoselective Synthesis of Taxane DerivativesSubstituted racemic 4,8,12-trinortaxanes were prepared stereoselectively in several steps from the dienone 10. A variant of the de Mayo reaction with bicyclononenones 4 and cyclohexen produced the desired configuration at C(8) of the taxane framework. Retro-aldol cleavage of the tetracycle 5 led to the taxane skeleton 6. Stereoselective reduction followed by treatment with base afforded 7b. Hydrolysis of the acetal group and further reduction yielded 9 in which the relative configuration corresponds to the one of the natural products.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720113
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  • 47
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    Asymmetric Diels-Alder reactions: X-Ray crystal-structure analysis of [N-((E)-But-2-enoyl)bornane-10,2-sultam]tetrachlorotitaniumPresented (WO) at the Annual Congress of the Royal Society of Chemistry, Canterbury, April, 1988. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 123-130 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An X-ray diffraction analysis of the crystalline complex 2b (MLn — TiCl4) shows a chelation of the carbonyl O-atom and the upper SO2 O-atom by TiCl4, a slightly pyramidal N-atom, and a π -face-stereoselective shielding of the C(α)-Si face by the CH2(3) group. The Ti-atom is in a pseudo-octahedral environment.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720116
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  • 48
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    Metal Complexes with Macrocyclic Ligands. Part XXVIIPart XXVI. Cu2+-promoted hydrolysis of carboxylic- and phosphonic-acid esters in the side chain of tetraazamacrocycles (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 131-138 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The X-ray structures of the Cu2+ complexes of 1,4,8,11-tetraazacyclotetradecane derivatives with an ethylpro-pionate and diethylphosphonate group, 5 and 6, respectively, indicate that the metal ion is pentacoordinated by the four N-atoms of the macrocycle and one O-atom. In the case of 5, it is the carbonyl O-atom of the carboxylate group, whereas for 6 it is the phosphonyl O-atom of the phosphonate group. The hydrolysis kinetics of the functional group in the Cu2+ complexes with the 1,4,8,11-tetraazacyclotetradecanes 3-6 have been measured by pH-stat and stopped-flow techniques. The rate law for the hydrolysis of the carboxylates 3-5 is proportional to the complex concentration and to [OH-] up to pH 13, whereas that of the phosphonate 6 is proportional to [OH-] up to pH 11.5, becoming independent of [OH-] at pH 〉 11.5. The mechanisms of these two reactions are discussed, considering the possibility of an intra- or an intermolecular OH- attack and the results of the X-ray structure analyses.
    Additional Material: 5 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720117
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  • 49
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    A New Method for the Preparation of (E)-3-Acylprop-2-enoic AcidsPresented in part at the autumn meeting of the Swiss Chemical Society in Bern on October 21, 1988.Dedicated to Prof. R. E. Ireland on the occasion of his 60th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 117-122 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new method for the preparation of (E)-3-acylprop-2-enoic acids ( = (E)-3-acylacrylic acids) of type II via acid-catalyzed isomerization of the corresponding 3-acylprop-2-ynal acetals of type I (Scheme 1) has been found. The described reaction gives a rapid and quite general access to these compounds known to exhibit a number of interesting biological activities. Some studies toward the elucidation of the reaction mechanism have been made, and a hypothetical mechanism is proposed.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720115
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  • 50
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    6-Thia-1-aza-5λ5-phosphabicyclo[3.2.0]hept-3-ene und Isothiocyanatophosphin-sulfide aus (Methylidenamino)phosphinen, Schwefelkohlenstoff und Acetylen- oder Ethylen-Derivaten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 139-146 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 6-Thia-l-aza-5λ5-phosphabicyclo[3.2.0]hept-3-enes and Isothiocyanatophosphine-sulfides from (Methylidenamino)phosphines, Carbon Disulfide, and Acetylene- or Ethylene Derivatives(Methylidenamino)phosphines react with carbon disulfide to 1,3,2-thiazaphosphete derivatives 2. Acetylenedicarboxylates give with 2 6-thia-l-aza-5λ5-phosphabicyclo[3.2.0]hept-3-enes 4a, b, and acrylates yield isothio-cyanatophosphin-sulfides 5a-c. The structures of 4a and 5a are proven by an X-ray diffraction analysis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720118
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  • 51
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    C45 und C50-Carotinoide. 6. Mitteilung5. Mitteilung, s. [1]. Synthese eines optisch aktiven cyclischen C20-Bausteins und von Decaprenoxanthin (= (2R, 6R, 2′R, 6′R)-2,2′-Bis(4-hydroxy-3-methylbut-2-enyl)-∊, ∊-carotin) (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 151-157 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: C45- and C50-Carotenoids: Synthesis of an Optically Active Cyclic C20-Building Block and of Decaprenoxanthin ( = (2R, 6R, 2′R, 6′R)-2,2′-Bis(4-hydroxy-3-methylbut-2-enyl)-∊, ∊-carotene)The synthesis of the optically active cyclic C20-building block (R, R)-15 and of the optically active C50-carotenoid (2R, 6R, 2′R, 6′R)-decaprenoxanthin (1) starting from (-)-β-pinene ((S)-2) is reported.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720120
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  • 52
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    Formation of the First Trimeric Monoterpenoid Indole Alkaloids (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 147-150 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Under O2, the Aspidosperma alkaloid tabersonine (1) was converted by a crude enzyme preparation from leaves of mature plants of Catharanthus roseus G DON into the trimeric 3-hydroxy-14′-(3α″-tabersonyl)voafrine B (4) which was easily reduced by NaBH4 to 14′-(3α″-tabersonyl)voafrine B ( = tertabersonine; 5). Compounds such as 4 and 5 are the first trimeric alkaloids in the series of monoterpenoid indole alkaloids.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720119
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  • 53
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    Polynuclear Iron and Rhodium Complexes of 7-Oxa[2.2.1]hericene (2,3,5,6-tetramethylidenebicyclo[2.2.1]heptan-7-one) (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 158-164 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: μ-Carbonyl(Rh—Rh)di(η5-indenyl)[(2R,3S)-C,2,3,C-η-(2,3,4,5-tetramethylidenebicyclo[2.2.1]heptan-7-one)]]-dirhodium(I)(Rh—Rh) (7) and cis-μ-[(2R,3S,5R,6S))-C,2,3,C-η:C,5,6,C-η-(2,3,5,6-tetramethylidenebicyclo[2.2.1]heptan-7-one)]bis[μ-carbonyldi(η5-indenyl)dirhodium(I)(Rh—Rh)] (8) have been prepared. Complex 7 reacts with Fe2(CO)9 in hexane/MeOH and gives cis-μ-[(2R,3S,5R,6S] (9), trans-μ-[(2R,3S,5S,6R)-C,2,3,C-η: C,5,6, C-η-(2,3,5,6-tetramethylidenebicyclo[2.2.1]heptan-7-one)-μ-carbonyldi(η5-indenyl)dirhodium(I)(Rh—Rh)-(tricarbonyliron) (10), and, μ-carbonyl(Rh—Rh)[(2R,3S)-C,2,3,C-η-(2,3-dimethyl-5,6-dimethylidenebicyclo-[2.2.1]hept-2-en-7-one)]di(η5-indenyl)dirhodium(I)(Rh—Rh) (11). Treatment of 7-oxa[2.2.1]hericene (4) with Fe2(CO)9 or (cyclooctene)2Fe(CO)3 gave a 1:2 mixture of cis-μ-[(2R,3S,5R,6S)-] (12) and trans-μ-[(2R,3S,5S,6R)-C,2,3,C-η:C,5,6,C-η-(2,3,5,6-tetramethylidenebicyclo[2.2.1]heptan-7-one)]bis(tricarbonyliron)(13).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720121
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  • 54
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    Eine neue Aminoazirin-Reaktion. Bildung von 3,6-Dihydropyrazin-2(1H)-onen (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 172-179 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A New Aminoazirine Reaction. Formation of 3,6-Dihydropyrazin-2(1H)-onesThe reaction of 3-(dimethylamino)-2H-azirines 1 and 2-(trifluoromethyl)-1,3-oxazol-5(2H)-ones 5 in MeCN or THF at 50-80° leads to 5-(dimethylamino)-3,6-dihydropyrazin-2(1H)-ones 6 (Scheme 3). Reaction mechanisms for the formation of 6 are discussed: either the oxazolones 5 react as CH-acidic heterocycles with 1 (Scheme 4), or the azirines 1 undergo a nucleophilic attack onto the carbonyl group of 5 (Scheme 6). The reaction via intermediate formation of N-(trifluoroacetyl)dipeptide amide 8 (Scheme 5) is excluded.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720123
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  • 55
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    Synthesis of the Oviposition-Deterring Pheromone (ODP) in Rhagoletis cerasi L. Preliminary communication (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 165-171 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: For the assignment of the configuration at C(8) and C(15) of the natural oviposition-deterring pheromone 1 in Rhagoletis cerasi L., the four possible stereoisomers of 1 are synthesized. By condensing the C6 building blocks (5R)-4 and (5S)-4 with the boron enolates of the C10 building blocks (4S)-13 and (4R)-13, followed by decarboxylative dehydration, all stereoisomers of 16 are available (Scheme 5). Glucosylation of 16 followed by formation of the taurin amide gives, after deprotection, the four stereoisomers (8R,15S)-1, (8R,15R)-1, (8R,15S)-1, and (8S,15S)-1 (Scheme 6).
    Additional Material: 1 Tab.
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    URL: http://dx.doi.org/10.1002/hlca.19890720122
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  • 56
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    Mitteilungen (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 185-192 
    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.19890720125
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  • 57
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    New Spermine Alkaloids from Aphelandra tetragona (VAHL) NEESDedicated to Prof. Dr. D. Gröger on the occasion of his 60th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 180-184 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 18-O-Methylchaenorpine (1a) and iso-18-O-methylchaenorpine (1b) two novel stereoisomeric spermine alkaloids were isolated from the roots of Aphelandra tetragona (VAHL) NEES. Their structures were established by chemical and spectroscopic studies.
    Additional Material: 2 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720124
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    Masthead (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989) 
    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.19890720201
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    1,5,7-Triazabicyclo[4.4.0]dec-5-en als Reaktionsmedium: Präparativ ergiebige einstufige Herstellung von Etioporphyrin aus Protoporphyrin (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 185-195 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,5,7-Triazabicyclo[4.4.0]dec-5-ene as Reaction Medium: An Efficient One-Step Formation of Etioporphyrine from ProtoporphyrineHeating the commercially available protoporphyrine (4) in molten 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) at 200° for 4 h under exclusion of O2 produces etioporphyrine (6) in 60-70% yield by bisdecarboxylation and concomitant reduction of the two vinyl groups. Mesoporphyrine (5) is bisdecarboxylated to 6 in over 80% yield under these conditions in TBD as well as in DBU as the reaction medium.
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    The Chemistry of Thujone. Part XIV.Part XIII [1]. Synthesis of biologically active aryl terpenoid analogues (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 205-212 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Employing thujone-derived intermediates, a series of achiral (9a-d; Scheme 1) and chiral (11b and 11d; Scheme 2) terpene analogues related to the biologically active ‘terpenoid’ hybrids have been prepared. The stereochemistry of the key epoxidation reaction was established by correlation of the product 11b with the previously reported alcohol (R)-20 of known absolute configuration (Scheme 3).
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    Vinyl Carbanions. Part 36.Part 35: [9]. Synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO) and derivatives (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 213-223 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The β-C-lithiated acrylamide 3A has been proven to be an ideal pyruvate β-carbanion equivalent useful in a highly diastereoselective KDO synthesis. The starting material 3 was prepared from pyruvate diethyl acetal in four convenient steps. Direct lithiation with 2 equiv. of LDA generated the dilithiated species 3A quantitatively. Reaction with 2,3:4,5-di-O-isopropylidene-D-arabinose (11) was highly D-manno-selective. The product 12 was obtained readily from the reaction mixture via crystallization. Ring closure to the butenolide 13, subsequent PhS-group removal with Bu3SnH and pyridinium bromide, and hydrogenolytic debenzylation afforded the known butenolide 19; this KDO precursor gives KDO in two convenient steps. Butenolide 19 was also transformed via two high-yielding steps into the 4,5:7,8-di-O-cyclohexylidene-KDO derivative 22, a valuable starting material for KDO α-glycoside syntheses.
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    Colchicine models: Synthesis and Antitubulin Activity of 2′-Monosubstituted and 2′, 5-Disubstituted 2,3,4,4′-Tetramethoxy-1,1′-biphenyls. Synthesis of 4,4′, 5′, 6′-tetramethoxy-1,1′-biphenyl-2,3′-dicarboxylic acidThis paper is dedicated to our friend and colleague Dr. Tetsuji Kametani, Hoshi College of Pharmacy, Tokyo, Japan, who died on October 11, 1988 (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 196-204 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reductive amination of 2,3,4,4′-tetramethoxtybiphenyl-2-carbaldehyde (4) with MeNH2 afforded methylamine 5 (Scheme 1), Hydroxymethylation of amine 8, prepared similarly from 4 by reductive amination with benzylamine followed by N-methylation, afforded alcohol 12 which was converted the 5-methyl-substituted methylamine 14 by conventional chemical reactions (Scheme 2), Methylamine 14 was also obtained from ester 16 after hydroxymethylation to alcohol 17 and conventional manipulation of alcohol and ester functions (Scheme 2). Both amines 5 and 14 as well as the 2′, 5-dimethyl-substituted biphenyl 26 prepared from the dialdehyde 25 by a Wolff-Kishner reduction, did not show noteworthy activity in the tubulin binding assay or as inhibitors of tubulin polymerization (Table). However, the 2′ethyl-substituted biphebyl 11 prepared from 4 by reaction with MeLi followed by dehyderation and catalytic reduction of styrene 10 (Scheme 1) showed appreciable activity in both assays, coming close to that of known phenyltropolone models. The X-ray analysis of 14·HCl and 11 showed significant difference in the orientation of the rings with respect to one another (Fig.).
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    Biosynthesis of Homoterpenes in Higher Plants (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 247-253 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In higher plants, the two homoterpenes 4,8-dimethyinona-1,3,7-triene (1) and 4,8,12-trimethyltrideca-1,3,7,11-tetraene (2) are synthesized from the regular terpene alcohols nerolidol and geranyllinalool by fragmentation into the homoterpene and butenone. The biosynthetic pathway is evidenced by conversion of (2H)nerolidol in Hoya purpureo-fusca, Magnolia liliiflora nigra, Robinia pseudoacacia, and Philadelphus coronarius.
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    URL: http://dx.doi.org/10.1002/hlca.19890720208
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    Sphinxolide, a 26-Membered Antitumoral Macrolide Isolated from an Unidentified Pacific Nudibranch (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 237-246 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: It is shown that an unidentified nudibranch of Hawaiian waters contains a 26-membered macrolide, sphinxolide ((-)-1) with potent activity against the KB cell line. The structure of sphinxolide, a 2:1 mixture of (E/Z)-isomers at the formamide moiety, is established to be (-)-1 on the basis of extensive NMR and FAB-MS analysis, in combination with data for the products of mono- (→(-)-2) and diacetylation (→(+)-3).
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    Synthesis of Aristotelia-Type Alkaloids.Part III: [1]. Part IV. Synthesis of (±)-aristoserratineDedicated to Prof. D. Arigoni on the occasion of his 60th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 254-263 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A convergent diastereoselective synthesis of racemic aristoserratine ((±)-24) via an intramolecular iminium-ion cyclization is described. The pivotal imine (±)-19 was prepared by condensation of the two building blocks (± )-trans-8-amino-3-(2,6-difluorobenzyloxy)-1-p-menthene ((±)-11) and N-(p-methoxybenzenesulfonyl)-3-indo-leacetaldehyde (18) which were synthesized from (±)-trans-1-p-menthene-3,8-diol ((±)-7) and 3-indoleacetic acid, respectively. On the route to the target (±)-24, two previously unknown indole alkaloids have been characterized, namely (±)-‘anti’-hobartin-15-ol ((±)-22) and (±)-‘anti’-aristotelin-15-ol ((±)-23).
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    URL: http://dx.doi.org/10.1002/hlca.19890720209
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    Syntheses of α, β-Epoxy Silyl Ketones (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 264-270 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the α, β-epoxy-acylsilanes 1 and 2 starting from the allylic silyl alcohols (E)- and (Z)-3, respectively, by epoxidation with t-BuOOH/VO(acac)2 followed by oxidation with Collins reagent (CrO3/pyridine) in up to 70% overall yields, is described. The acid-catalyzed rearrangement of the epoxy-silyl alcohols 4A + B und 5A + B led to the novel unstable diastereoisomeric α-silyl-β-hydroxy-aldehydes 9 and 10, respectively. The structure of 10 was established by X-ray crystal-structure analysis of the corresponding alcohol 11.
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    URL: http://dx.doi.org/10.1002/hlca.19890720210
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    Spectroscopic Studies of Cyclometallated Pd(II) and Pt(II) Complexes: Optical absorption and emission of single crystals of [Pd(thpy)2] and [Pt(thpy)2] (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 224-236 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The polarized optical absorption and emission (spectra, decay times) of single crystals of [Pd(thpy)2] and [Pt(thpy)2] (thpy ≡ C(3′)-deprotonated form of 2-(2-thienyl)pyridine) at temperatures 1.9 K ≤ T ≤ 80 K are reported. The emission of [Pt(thpy)2] can be influenced strongly by applied magnetic fields (0 ≤ H ≤ 6 T). Depending on the central ions Pd and Pt, the lowest excited electronic states of the single complexes are ligand-centered (LC) states and metal-to-ligand charge transfer (MLCT) states, respectively. This difference leads to distinctly dissimilar properties of the emission of both compounds. The experimental data show that the emission of single crystals of [Pd(thpy)2] and [Pt(thpy)2] at T ≤ 30 K originates from several types of traps (defect states of symmetry 3B2-stabilized below the exciton band) with LC and MLCT character, respectively. In the Pt compound, the 3B2 is split by spin-orbit coupling into three states. The states B1′ and A2′, which determine the emission properties, are separated by Δv ∼ 13 cm-1. Both states can mix under the influence of an applied magnetic field yielding an increase of the emission intensity by a factor of ∼ 1.5 at H = 6 T.
    Additional Material: 14 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720206
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    Total Synthesis of L-Allose, L-Talose, and derivatives.Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (‘naked sugars’ [2]) as synthetic intermediates, Part IV. Part III, see [1]. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 278-286 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (1S, 4R, 5S, 6S)-5-exo, 6-exo-(Isopropylidenedioxy)-7-oxabicyclo[2.2.1]heptan-2-one ((-)-1) was transformed with high stereoselectivity to L-allose. Similarly, enantiomer (+)-1 was transformed into L-talose. The ketones (+)-1 and (-)-1 were derived from furan and 1-cyanovinyl (1S)-camphanate and 1-cyanovinyl (1R)-camphanate, respectively.
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    URL: http://dx.doi.org/10.1002/hlca.19890720212
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    Highly Stereoselective Total Syntheses of 2,5-Anhydro-4-deoxy-D-ribo-hexonic Acid and of (1S)-1-C-(6-amino-7H-purin-8-yl)-1,4-anhydro-3-deoxy-D-erythro-pentitol (= cordycepin C)Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (‘naked sugars’) as synthetic intermediates, Part V. Part III: [1]. Part IV: [2].Part of the planned Ph. D. thesis of F. G., University of Lausanne.Dedicated to Prof. Hans Dahn on the occasion of his 70th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 271-277 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Highly regio- and stereoselective monohydroxylation of the C=C bond of (+)-7-oxabicyclo[2.2.1]hept-5-en-2-one (8) was achieved via LiAlH4 reduction of the corresponding 5,6-exo-epoxy dimethyl acetal 9. The reaction gave exclusively (-)-(1R, 2R, 4S)-6,6-dimethoxy-7-oxabicyclo[2.2.1]heptan-2-exo-ol (10) which was transformed into 2,5-anhydro-3-O-benzyl-4-deoxy-D-ribo-hexonic acid (15) and 2,5-anhydro-4-deoxy-D-ribo-hexonic acid (6) via ozonolysis of (-)-(1R, 4S, 6R)-6-exo-benzyloxy-2-{[(tert-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]hept-2-ene (14). Cordycepin C (5) was derived from 6 and 4,5,6-triaminopyrimidine using CsF/DMF to generate the adenine heterocycle.
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    URL: http://dx.doi.org/10.1002/hlca.19890720211
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    Die absolute Konfiguration der Iridale und Cycloiridale unterschiedlicher HerkunftDr. G. Ohloff zum 65. Geburtstag mit den besten Wünschen gewidmet (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 287-294 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The Absolute Configuration of Iridals and Cycloiridals of Different OriginNatural irones are known to occur in enantiomeric forms within Iris oils of different origin. They are formed by oxidative degradation of the cycloiridals (C31-triterpenoids) found in rhizomes of various Iris species. The absolute configuration of iridals from different varieties is determined by ozonolysis of the triterpenoids and comparison of their degradation products with authentic samples of known configuration. It is shown that the initial cyclization of squalene resulting in the formation of a monocyclic seco-ring-A iridal has the same stereo-chemical course throughout all Iris species studied. The subsequent cyclization of the homofarnesyl side chain of the iridals, however, produces cycloiridals with enantiomeric irone moieties within different subspecies of the sword lilies.
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    URL: http://dx.doi.org/10.1002/hlca.19890720213
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    Metal Complexes with Macrocyclic Ligands. Part XXVIII.Part XXVII: [1]. Structures and stabilities of the Cu2+ complexes with 1,4,7-triazacyclononane-1-acetic acid (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 307-312 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The potentiometric study of the complexation of 1,4,7-triazacyclononane-l-acetic acid (1) with Cu2+ (I = 0.5 (KNO3), T = 25°) indicates the presence of the species [Cu(1)], [Cu(1)OH], [Cu(1)2], and [(Cu(1))2OH], the stability constants of which are determined. The two complexes [Cu(1)]ClO4 and [(Cu(1)2)OH]ClO4 were also characterized by X-ray structure analysis. In both cases, the Cu2+ ion is in a distorted square-pyramidal arrangement, penta-coordinated by the three N-atoms of the macrocycle, an O-atom of the carboxylate, and an additional O-atom either from a second carboxylate or from an OH-, acting as a bridge between two metal centres.
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    URL: http://dx.doi.org/10.1002/hlca.19890720215
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    Metal Complexes with Macrocyclic Ligands. Part XXIX.Part XXVIII: [1]. Structural and kinetic studies of two isomeric Cu2+ complexes with 1,4-dimethyl-8-[2-(2-pyridyl)ethyl]-1,4,8,11-tetraazacyclotetradecane (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 313-319 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis and complexation properties of 1,4-dimethyl-8-[2-(2-pyridyl)ethyl]-1,4,8,11-tetraazacyclotetra-decane (2) are described. This ligand forms with Cu2+ two complexes, one of which has been characterized by X-ray structure analysis. The structural, spectral, and kinetic studies indicate that the two Cu2+ complexes are isomers with the macrocycle in the trans-III and trans-I configuration. The rate of the interconversion of the trans-I isomer to the thermodynamically more stable trans-III species is proportional to [OH-]. A mechanism for this reaction is proposed.
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    URL: http://dx.doi.org/10.1002/hlca.19890720216
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    Stereochemical Criteria Providing Unambiguous Experimental Evidence for the intermediacy of ion/molecule complexes in the generation of enolates from gaseous alkoxides. Short communicationDedicated to Prof. Josef Seibl on the occasion of his 65th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 320-322 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The epimeric alkoxides 6a and 6b, generated in the gas phase by deprotonation of the stereospecifically deuterated isoborneols 5a and 5b, undergo loss of H2 and HD in a 1:1 ratio. This result, ruling out a concerted one-step process, establishes the intermediacy of an ion/molecular complex (‘solvated’ hydride ion) in the course of formation of enolates from the alkoxide anions in the gas phase.
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    URL: http://dx.doi.org/10.1002/hlca.19890720217
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    Neue Dimethinmerocyanin-Farbstoffe mit der (Sulfobutyl)benzothiazol-Gruppe als Donor-Teilchromophor und deren Aggregationsverhalten in wässriger Lösung (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 295-306 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Novel Dimethinemerocyanine Dyes with the (Sulfobutyl)benzothiazole Group as Donor Part of the Chromophor and their Aggregation Tendency in Aqueous SolutionA series of novel dimethinemerocyanine dyes with the (sulfobutyl)benzothiazole group as the donor part of the chromophor is synthesized in good yield and their aggregation tendency in H2O without addition of salt investigated. The merocyanine dye 2b only gives J-aggregation in H2O. The dyes 1a-f and 2a exhibit an intense, red-shifted absorption band due to J-aggregation in H2O in the presence of Me4NCl. In contrast, the dyes 1g and 2c-f show a slightly red-shifted absorption band. The degree of aggregation in H2O is investigated by ultracentrifugation of the representative 2e. Indeed, the slightly red-shifted absorption band in H2O is due to aggregation of ‘oligomers’ of the dye. Contrary to the aggregation of ‘polymers’ of dyes (J-aggregation), we suggest the term ‘K’ band for the slightly red-shifted absorption band. The hemicyanine dye 5 gives the same absorption band in MeOH and in MeOH/H2O 1:3. The dye 11 shows an absorption band in H2O that is probably blue-shifted because of negative solvatochromism. The merocyanine dye 13 gives H-aggregation in H2O.
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    URL: http://dx.doi.org/10.1002/hlca.19890720214
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    Models for Copper-Dioxygen Complexes: The chemistry of copper(II) with some planar tridentate nitrogen ligands (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 323-337 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The solution chemistry of Cu(II) with a series of five planar tridentate nitrogen ligands, 2,6-bis(benzimidazol-2-yl)pyridine (bzimpy, 1), 2,6-bis(l-methylbenzimidazol-2-yl)pyridine (mbzimpy, 2) 2,6-bis(benzothiazol-2-yl) pyridine (bzthpy, 3), 2,6-bis(benzoxazol-2-yl)pyridine (bzoxpy, 4), and 2,2′, 6′, 2″-terpyridyl (terpy, 5) is reported. Electronic and EPR spectra are consistent with the complexes [CuL]2+ having essentially tetragonal structure in solution, with the fourth coordination site in the plane of the ligand occupied by solvent. bzthpy and bzoxpy show smaller ligand-field splittings than bzimpy, mbzimpy, and terpy, and are easily decomplexed from the copper. Substitution of the coordinated solvent molecule in the plane of the ligand is observed with Cl- and OH- (provided that the ligand has no acidic protons) for all ligands except terpy. The reaction between [Cu(mbzimpy)]2+ and imidazole has been studied by potentiometric titration in MeCN/H2O 1:1 and shows strong binding of the imidazole in the plane (log K = 4.5 at 25°), and also the formation of an imidazolate-bridged dinuclear species.
    Additional Material: 3 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19890720218
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    Synthesis of (-)-Conduritol C (1L-Cyclohex-5-ene-1,2,3/4-tetrol)Enantiomerically pure 7-oxabicyclo[2.2.1]hept-5en-2-yl derivatives (‘naked sugars’ [1]) as synthetic intermediates, Part VI; Part V:[2]. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 338-347 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (1R, 2R, 4R)-2-endo-Cyano-7-oxabicyclo[2.2.1]hept-5-en-2-yl acetate ((-)-7) has been transformed into the all-cis-configurated 4L-4,5,6/0-trihydroxycyclohex-2-en-1-one derivatives (-)-12 and (-)-19. (-)-Conduritol C ((-)-3) was derived in a stereospecific manner from (-)-12.
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    URL: http://dx.doi.org/10.1002/hlca.19890720219
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    Diels-Alder-Reaktionen mit 3-Cyclopropylidenprop-1-enyl-ethyl-ether als 1,3-Dien (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 348-352 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Diels-Alder Reactions with 3-Cyclopropylideneprop-1-enyl Ethyl Ether as 1,3-DieneThe title compound undergoes readily Diels-Alder reactions with various dienophiles, especially with quinones. The resulting adducts constitute key intermediates in the synthesis of labdane diterpenoids.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720220
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  • 78
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    Synthese von (+)-Abscisinsäure (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 361-364 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of (+)-Abscisic Acid.Starting from (4S)-4-hydroxy-2,6,6-trimethylcyclohex-2-enone (2), a short synthesis of the natural (+)-abscisic acid ((+)-1) has been accomplished.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720222
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  • 79
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    Ein neuer Zugang zu 2,6,6-Trimethylcyclohexa-2,4-dienon aus 4-Oxoisophoron (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 365-369 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A New Access to 2,6,6-Trimethylcyclohexa-2,4-dienone from 4-Oxoisophorone2,6,6-Trimethylcyclohexa-2,4-dienone (1), a versatile starting material for the preparation of some carotenoids and several natural products, was efficiently (73% yield) prepared from oxoisophorone 3. After conversion of 3 to the alcohol 4 or the acetate 5, H2O was eliminated (4→1) under acidic distillative conditions, whereas AcOH could be eliminated (5→l) under Pd(O) catalysis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720223
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  • 80
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    Neue Zugänge zu einigen aromatischen Retinoiden (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 370-376 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New Approaches to Some Aromatic RetinoidsStarting from 2,3,5-trimethylphenol (2), two pathways to ethyl (all-E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate (1) and to some of its (Z)-isomers have been developed. The first one is based on a Pd(O)-catalyzed arylation of (Z)-3-methylpent-2-en-4-yn-l-ol (6) with 4-bromo-2,3,5-trimethylanisol (5). The acetylenic C15-alcohol 9 was transformed into the corresponding acetylenic phosphonium salt 10, which was catalytically hydrogenated to the olefinic Wittig salt. Wittig olefination led, then, to the (6Z, 8Z)- and (4Z, 6Z, 8Z)-isomers, 7 and 8, respectively. In a second approach, Friedel-Crafts reaction of 3-methylpent-l-en-4-yn-3-ol with the 2,3,5-trimethylanisol gave a C15-intermediate with a terminal C=C bond in the side chain. After deprotonation and reaction with a C5 aldehyd, the corresponding C20-intermediate could be isolated in high yield. Finally, further conversion led predominantly to the (all-E)-retinoid, accompanied by its (9Z)- and (13Z)-isomers.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720224
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  • 81
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    Synthesis of Gossypol AnaloguesDedicated to the memory of Professor Dr. Pierre Crabbé (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 353-360 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two gossypol analogues 2a and 2b were synthesized for biological evaluation as male contraceptive agents. The naphthol 8c was prepared by analogy with a known procedure starling from 3-isopropylcatechol (3). (t-Bu)2O2-Mediated phenolic coupling of 8c furnished the binaphthol 9c which, after pyrane ring closure, deprotection. and selective bisformylation with SnCl4/Cl2CHOCH3, gave the target compound 2a. The corresponding tetrahydroxy analogue 2b was prepared in a similar way.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720221
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  • 82
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    Cyclometalated Compounds of Platinum(II) with two different C, N-aromatic ligands (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 377-382 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A synthetic route leading to bis-heteroleptic cyclometalated complexes is described. The complexes [2-(2′-thienyl)pyridinato-N, C-3′]{2-[3′-(trimethylsilyl)2′-thienyl]pyridinato-N, C3′}platinum(II) ([Pt(thpy) (TMS-thpy)]; I) and (l-phenylpyrazolato-N2, C2′)[2-(2′-thienyl)pyridinato-N, C3′]platinum ([Pt(Phpz)(thpy)]; II) are characterized by UV/VIS, NMR, and mass spectroscopy. Thermal and photochemical oxidative addition reactions yield two out of the 10 possible pairs of enantiomers of octahedral Pt(IV) compounds.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720225
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  • 83
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    Masthead (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989) 
    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.19890720301
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  • 84
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    Mitteilungen (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 401-402 
    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.19890720228
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  • 85
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    The Radical Cations of Bicyclo[2.2.1]hepta-2,5-diene (8,9,10-Trinorborna-2,5-diene) and bicyclo[2.2.2]octa-2,5-diene (2,3-Dihydrobarrelene). An ESR and ENDOR studyPart 5 of ‘Applications of ENDOR Spectroscopy to Radical cations in Freon matrices’. Part-4: [1]. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 383-390 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The radical cation of bicyclo[2-2.1]hepta-2,5-diene (8,9,10-trinorborna-2,5-diene; 1) in CF2ClCFCl2, and CF3CCl3 matrices and that of bicyclo[2.2.2]octa-2,5-diene (2,3-dihydrobarrelene; 2) in CFCl3 and CF3CCl3 matrices have been studied by ESR and ENDOR spectroscopy. For \documentclass{article}\pagestyle{empty}\begin{document}${\bf 1}^{+ \atop \dot{}}$\end{document}, the coupling constants of the olefinic, methano-bridge, and bridgehead protons are -0.780 ±0.005, +0.304±0.002, and -0.049±0.002 mT, respectively. The hyperfine tensor for the methano-bridge protons is axial, Ax = +0.263 ± 0.002 and Ay = +0.386 ± 0.002 mT, while that for the olefinic protons is orthorhombic, Ax = -0.594 ± 0.005, Ay= -0.913 ± 0.005, and Az = -0.834 ± 0.005 mT (x parallel to C—H- z parallel to 2pπ axis). For \documentclass{article}\pagestyle{empty}\begin{document}${\bf 2}^{+ \atop \dot{}}$\end{document}, the coupling constants of the olefinic, ethano-bridge, and bridgehead protons are -0.68 ± 0.01, +0.162 ± 0.005, and -0.108 ± 0.005 mT, respectively. The hyperfine data for \documentclass{article}\pagestyle{empty}\begin{document}${\bf 1}^{+ \atop \dot{}}$\end{document} and \documentclass{article}\pagestyle{empty}\begin{document}${\bf 2}^{+ \atop \dot{}}$\end{document} fully support the presentation of their singly occupied orbitals as antisymmetric combinations, b2(π), of the two bonding ethene π-MO's.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720226
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  • 86
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    The Allylic Oxidation of Geraniol Catalyzed by Cytochrome P-450Cath., Proceeding with retention of configurationPresented in part at the ‘22nd Reaction Mechanisms Conference’, Pittsburgh, 12.6-16.6.88, at the ‘6th International Conference on Biochemistry and Biophysics of Cytochrome P-450’, Vienna, 3.7.-8.7.88, and at the meeting on the ‘Biocatalytic synthesis of Organic Compounds’, Saratoga Springs, NY, 8.-12.8.88.Dedicated to Prof. D. Arigoni on the occasion of his 60th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 391-400 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Incubation of the geraniols (R)-(8-2H1)[8-3H1]-1 and (S)-(8-2H1)[8-3H1]-1 with microsomal cytochrome P-450Cath. from the subtropical plant Catharanthus roseus (L.)G. DON resulted in the formation of the chiral 8-hydroxygeraniols (S)-(8-2H1)[8-3H1]-2 and (R)-(8-2H1)[8-3H1]-2. Their absolute configuration was assigned on the basis of the 1H-decoupled 3H-NMR Spectra of the corresponding dicamphanates (S)-(8-2H1)[8-3H1]-9 and (R)-(8-2H1)[8-3H1]-9, of which the configurations are established in relation to the synthetic reference samples. The results clearly indicate retention of configuration during the allylic oxidation of 1.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720227
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  • 87
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    Elektrochemische Decarboxylierung von L.-Threonin- und Oligopeptid-Derivaten unter Bildung von N-Acyl-N, O-acetalen: Herstellung von Oligopeptiden mit Carboxamid-oder Phosphonat-C-TerminusTeilweise in einer Kurzmitteilung erwähnt (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 401-425 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Electrochemical Decarboxylation of L-Threonine and Oligopeptide Derivatives with Formation of N-Acyl-N, O-acetals: Preparation of Oligopeptides with Amide or Phophonate C-TerminusDerivatives of α-amino acids with two stereogenic centers (cf. L-threonine) and of di-, tri-, and tetrapeptides are electrolyzed in MeOH or AcOH, with formation of N-acyl-N, O-acetals (1b-15b, 20b), in an anodic oxidative substitution of the COOH by an OR group. The amine ends of the oligopeptides may be benzyloxycarbonyl(Z)- or (tert-butoxy)carbonyl(Boc)-protected. With unprotected dipeptides, an electrolytic decarboxylative cyclization to imidazolidinones (18c, 19c) may also occur (in H2O/NH4OAc). The electrolyses are carried out in simple flasks with cooling jackets (‘undivided cell’), using constant current conditions and anodes of Pt or glassy C. The electrolyte is generated in situ by adding 10-20 mol-% of a tertiary amine. Mild acidic hydrolysis of electrolysis products thus obtained may lead to amino-acid amides or peptide amides (10c, 11c, 12c, 17c) with one amino acid less than the starting material. The N, O-acetals from L-threonine and the oligopeptides also react with organometallic nucleophiles such as Grignard compounds (→21-26, 29), with formation of products in which the original COOH group has been replaced by alkyl or allyl (sometimes even with moderate stereoselectivity). By treatment of the peptide-derived (open-chain) N, O-acetals with trialkyl or triaryl phosphites/TiCl4 the RO group is replaced by a phosphodiester group in a (non-diastereoselective) Michaelis-Arbuzov-type reaction (1d, 1e, 2d-9d, 5e). Thus, the two-step sequence of electrolysis and phosphonation converts an oligopeptide derivative to an analogue with a phosphonic-acid end group. The diastereoisomeric N-protected dimethyl and diethyl dipeptidephosphonates (also prepared from the corresponding diaryl esters by Ti(OR)4-mediated transesterification) could be separated by preparative HPLC (SiO2, Lichrosorb Si 60, 10 μm); the dextrorotatory isomers of 1d-3d were assigned L, D-, the laevoratory ones L, L-configuration by hydrolysis to and identification of the known amino and aminophosphonic acids. The results described demonstrate a new simple route leading, from a given oligopeptide, to pure peptide analogues of known configuration.
    Notes: No abstract.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720302
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  • 88
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    Acid-Catalyzed Cyclization Reactions of Substituted Acetylenic Ketones: A new Approach for the Synthesis of 3-Halofurans, Flavones, and StyrylchromonesPresented in part at the autumn meeting of the Swiss Chemical Society in Bern on October 21, 1988. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 447-456 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Acetylenic acetals of type I (Scheme 1) and acetylenic ketones of type III (Scheme 1), 37 and 38 (Scheme 7) are versatile synthetic precursors for the synthesis of various heterocycles by acid-catalyzed cyclization reactions. By this way, substituted 3-halofurans of type II and IV (Scheme 1) and flavones and styrylchromones (Scheme 7) can be synthesized in good-to-excellent yields. The high degree of regioselectivity in the synthesis of the 3-halofurans (Scheme 4) is the result of the regioselective β-addition of HX (X = Cl, Br, I) to the acetylenic aldehyde and acetylenic ketone moieties. A possible mechanism is depicted in Scheme 5. Since 3-halofurans can easily be metalated and substituted, this approach constitutes a new synthesis of highly substituted furans.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720305
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  • 89
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    Stoffwechselprodukte von Mikroorganismen. 253. Mitteilung252, Mitteilung. Hormaomycin, ein neues Peptid-lacton mit morphogener Aktivität auf Streptomyceten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 426-437 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hormaomycin, a Novel Peptide Lactone with Morphogenetic Activity on StreptomycesA culture identified as Streptomyces griseoflavus (strain W-384) has been found to produce a novel peptide-lactone antibiotic designated hormaomycin (6). The empirical molecular formula of the compound is established to be C55H69ClN10O14. The constituent amino acids of the antibiotic are suggested to be allothreonine (1; 1), isoleucine (2; 1), 3-methyl-phenylalanine (3; 2), and, for the first time identified from a natural source, 4-[(Z)-prop-1-enyl]-proline (4; 1) and 3-(2-nitrocyclopropyl)-alanine (5; 2). The amino acids were delivered by acidic hydrolysis and assigned by high-resolution- GC/MS analysis (after transformation to derivatives) in combination with extended 2D-NMR experiments of the antibiotic itself. From the latter, it became plausible that the N-terminus of the peptide chain is acylated by a Cl-containing derivative of 1H-pyrrol-2-carboxylic acid. Hormaomycin is active against some Gram-positive bacteria. In addition, the antibiotic exhibits potent aerial mycelium-inducing activity and effects the production of antibiotics.
    Notes: No abstract.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720303
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  • 90
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    Novel Trinor-eremophilanes (Dendryphiellin B, C, and D), Eremophilanes (Dendryphiellin E, F, and G), and Branched C9-Carboxylic Acids (Dendryphiellic Acid A and B) from the Marine Deuteromycete Dendryphiella salina (SUTHERLAND) PUGHet NICOT (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 438-446 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Further investigation of global extracts from cultures of the marine deuteromycete Dendryphiella salina leads to the isolation of three novel trinor-eremophilanes esterified by branched C9-carboxylic acids, dendryphiellin B(= (+)-(1R*,2S*,7R*,8aR*)-1,2,6,7,8,8a-hexahydro-7-hydroxy-1,8a-dimethyl-6-oxonaphthalen-2-yl (6R*, 2E, 4E)-6-hydroxy-6-methylocta-2,4-dienoate; (+)-2), dendryphiellin C (=(+)-(1R*, 2S*, 7R*, 8aR*)-1,2,6,7,8,8a-hexa-hydro-7-hydroxy-1,8a-dimethyl-6-oxonaphthalen-2-yl (6S, 2E, 4E)-6-methylocta-2,4-dienoate; (+)-3)), and dendryphiellin D (=(+)-(1R*, 2S*, 7R*, 8aR*)-1,2,6,7(8,8a-hexahydro-7-hydroxy-1,8a-dimethyl-6-oxonaphthalen-2-yl (6R*,2E,4E)-6-(hydroxymethyl)octa-2,4-dienoate; (+)-4). An intact eremophilane, dendryphiellin E (5), and its ethanolysis product dendryphiellin F whose absolute configuration is represented by structural formula (+)-6 are also isolated from the above extracts. Dendryphiellin E exists as an open form 5a in equilibrium with a closed form 5b. A similar equilibrium exists between the open form 8a and the closed form 8b of a non-esterified eremophilane, dendryphiellin G (8), which is isolated too from the above extracts and proves structurally related to the cyclic portion of 5. Finally, the free, branched C9-carboxylic acids dendryphiellic acid A ((+)-9) and B ((+)-10) which correspond to side chains of the above esterified terpenes are also isolated from the above extracts.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720304
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  • 91
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    Eine neue Azepinring-Synthese (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 457-463 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A New Azepine-Ring SynthesisA new one-step synthesis of an azepine ring is described. The 2H-pyran-2-one ring of methyl cumalate (8) or cumalaldehyde (2) upon reaction with an 1-aminoacryl derivative, e.g. 1 or 6, is opened with subsequent decarboxylation to give a 1-aminobutadiene derivative that undergoes an electrocyclic ring closure to the azepine ring (Schemes 1 and 2).
    Notes: No abstract.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720306
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  • 92
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    New Hyperforin Derivatives from Hypericum revolutum VAHL with Growth-Inhibitory Activity against a Human Colon Carcinoma Cell LinePresented in part at the 36th Annual Congress on Medicinal Plant Research, Freiburg im Breisgau, FRG, 12-16th September, 1988, and at the Meeting of the Swiss Chemical Society, Bern, 21st October, 1988. (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 464-471 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The crude petroleum-ether extract of the root bark of Hypericum revolutum VAHL (Guttiferae) exhibited in vitro growth-inhibitory activity against the Co-115 human colon carcinoma cell line. Activity-guided fractionation of this extract resulted in the isolation of two new hyperforin derivatives 1 and 2. The structure of 1 (hyperevolutin A) was established by X-ray analysis as the 4-hydroxy-8-exo-methyl-5,7-exo-bis(3-methylbut-2-enyl)-1-(2-methyl-1-oxopropyl)-8-endo-(4-methylpent-3-enyl)bicyclo[3.3.1]non-3-ene-2,9-dione. The structure of the homologue 2 was deduced by comparison of its UV and 1H- and 13C-NMR spectra with those of 1.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720307
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  • 93
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    Asymmetric Diels-Alder Reaction of 1-Methoxybuta-1,3-diene with (2R)-N-Glyoxyloylbornane-10,2-sultam (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 482-486 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Starting from sultam 1, the chiral dienophile (2R)-N-glyoxyloylbornane-10,2-sultam (4) was readily prepared. Non-catalyzed atmospheric- and high-pressure as well as [Eu(fod)3]-promoted [4 + 2] cycloadditions of 1-methoxy-buta-1,3-diene (5) to chiral dienophile 4, leading with high asymmetric induction to 6-methoxy-3,6-dihydro-2H-pyran-2-yl derivatives 6-9, are described. The extent and direction of asymmetric induction in these reactions were established by 1H-NMR analysis and chemical correlation, respectively. Stereochemical models for both non-catalyzed and [Eu(fod)3]-promoted reactions are proposed.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720310
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  • 94
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    5,10:8,9-Disecosteroids (= Steroklastanes): A new type of modified steroidsDr. Günther Ohloff on the occasion of his 65th birthday (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 608-623 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thermolysis of steroidal 5α, 8α- peroxides of type 3a-d generates as major products the corresponding diseco compounds containing a 14-membered ring instead of the standard A-B-C-ring skeleton. Depending on the reaction conditions, either the primary products of type 9 or the α, β-unsaturated ketones of type 4, formed by subsequent elimination of AcOH, are isolated. The latter, configurationally uniform compounds undergo epoxidation of the C(9)=C(10) bond followed by a Baeyer-Villiger oxidation to give, as final products, the 15-membered cyclic epoxyenol lactones of type 20 and 21. The structures of the various products were determined by 1H- and 13C-NMR spectroscopy. The conformations of the 14- and 15-membered rings were established by X-ray structure analyses of 7 and 21a. A reaction mechanism for the above transformations is discussed.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720320
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  • 95
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    Thermal and Photochemical Reactions of 1,2-Annelated Barrelenes and Hydrobarrelenes in the presence of transition-metal carbonyls (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 648-652 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The [Co2(CO)8]-mediated retro-Diels-Alder reaction of the annelated barrelenes 1 afforded the 1H-indol-2(3H)-one derivatives 3 (Scheme 1), while the hydrobarrelene 4a, under the same conditions, was converted to the anilide 6 (Scheme 2); 4b remained unaffected. The direct irradiation of 1 led to the annelated cyclooctatetraenes 7 (Scheme 3). On irradiation in the presence of excess of [Fe(CO)5], 1a, 1b, and 4a gave the tricarbonyliron complexes 8, 9, and 11, respectively (Schemes 3 and 4); under these conditions, 4b was inert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720404
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  • 96
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    A Simple and Efficient Method for the Preparation of Binaltrorphimine and Derivatives and determination of their K opioid antagonist selectivity (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 675-677 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The bimorphinans 1 (binaltrorphimine), 3, and 7 have been prepared by treatment of the parent morphinan-6-ones naltrexone (5), naloxone (4), and dihydrocodeinone (6), respectively, with N-methylhydrazine sulfate in AcOH at room temperature. Compound 3 showed opioid antagonist potency and selectivity for K receptors which were somewhat lower in comparison to 1.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720408
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  • 97
    Electronic Resource
    Electronic Resource
    Synthèse d'une sonde biotinylée à bras clivable allongé pour l'isolement des récepteurs de l'angiotensine II (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 678-689 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of a Biotinylated Probe with an Extended Cleavable Arm for Angiotensin II Receptors PurificationWe have synthesized a new biotinylated probe for angiotensin II receptors studies: biotinyl-NH(CH2)2—SS—(CH2)2—CO-Gly-∊ Ahx-[Ala1, Phe(4N3)8]angiotensin II (5). This molecule can be photoactivated through an arylazido group. 1H-NMR studies suggest that it adopts an extended conformation which should allow a simultaneous recognition of both streptavidin and hormone receptor. It has a good affinity for receptors (Kd = 1 nM) and hence is a promising tool in their detection (autoradiography, gold-, ferritin-, enzyme-, or fluorescent streptavidin derivatives) and separation (cell sorting, affinity chromatography). It can be monoiodinated (°6) at its tyrosine residue without a significant loss of affinity. Its extended cleavable arm allows an easy recovery of the ‘probe-receptor’ complex from streptavidin. An HPLC monitoring of the synthesis is described, particularly of the segment coupling 1 + 2 in presence of (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP). This method can be used as well for synthesis of the D-Phe8 derivative that has antagonist properties.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720409
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  • 98
    Electronic Resource
    Electronic Resource
    Synthesis of 11-Oxaestrogens via Dye-Sensitized Photo-oxygenation of a 9,11-Didehydroestrone Derivative (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 725-730 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 3-methoxy-1 1-oxaestrone (13) has been synthetized from estrone (3) following an approach that involves the ring-C fragmentation of the estrogenic skeleton by dye-sensitized photo-oxygenation of the properly C(17)-protected 9,11-didehydroestrone derivative 6 as the key step. The C(13)-side-chain degradation of the 9-oxo-9,11-seco-aldehyde 7 followed by reduction to the 9β, 12-diol 10 and further cyclization yields the 11-oxaestrogenic skeleton. By this procedure, 13 is obtained in 9 steps from 3 with a non-optimized overall yield of ca. 15%.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720412
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  • 99
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    Electronic Resource
    Photo-oxygenation of Styrenic Estrogens: Product characterization and kinetics of the dye-sensitized photo-oxygenation of 9,11-didehydroestrone derivativesPhotochemical Reactions, Part 23. Part 22: [1] (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 715-724 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The dye-sensitized photo-oxygenation of 3-hydroxyestra-1,3,5(10), 9(11)-tetraen-17-one (8) gives a complex mixture from which only the 1,4-endo-peroxide 10 can be isolated in low yield. In contrast, the 3-methoxy derivative 9 yields the C-seco-aldehyde 11 as a major product, suggesting that 1,2-dioxetane is a primary photo-oxygenation intermediate. As the electron-donating character of the substituent at C(3) decreases in the sequence 12 (R = PhCO), 13 (R = Ac), and 14 (R = Ts), the rate constant in substrate disappearance becomes drastically smaller as compared with 8 and 9, and no photoproducts are detected. The results are rationalized by means of electronic and conformational factors.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720411
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  • 100
    Electronic Resource
    Electronic Resource
    Synthèse énantiospécifique des acides (+)-(2R)- et (-)-(2S)-éthyl-6-dihydro-3,4-méthyl-2-oxo-4-2H pyranecarboxylique-5 (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 731-737 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Enantiospecific Synthesis of (+)-(2R)- and (-)-(2S)-6-Ethyl-3,4-dihydro-2-methyl-4-oxo-2H-pyran-5-carboxylic AcidThe two enantiomers (-)-(2S)- and (+)-(2R)-6-ethyl-3,4-dihydro-2-methyl-4-oxo-2H-pyran-5-carboxylic acid ((S)- and (R)-7) have been synthesized from (+)-(3S) and (-)-(3R)-3-hydroxybutanoates, respectively (Scheme 1). By reduction and decarboxylation, the tetrahydro-2H-pyranols (2R, 4R, 6S)- and (2S, 4S, 6R)-13, respectively, were obtained with an enantiomeric excess of ≥ 93%.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720413
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