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  • 2000-2004
  • 1995-1999  (812)
  • 1999  (812)
  • General Chemistry  (750)
  • Amino acids  (73)
  • Nuclear reactions
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  • 2000-2004
  • 1995-1999  (812)
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Keywords
  • 1
    Electronic Resource
    Electronic Resource
    Determination of the protooncogene ets-2 gene transcript in human brain at the atto-gram-level by the use of competitive RT/PCR (1999)
    Springer
    Amino acids 16 (1999), S. 13-19 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; RT/PCR ; Protooncogene ; ets-2
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Protooncogenes (PO) play a crucial role for brain biology and pathology. Only the concerted action of protooncogenes enables normal brain development. The reliable and sensitive quantification of brain PO is still holding centre stage in neurobiological research. The aim of our study was therefore the determination of PO in minute amounts of brain areas. For this purpose we decided to apply the most sensitive detection principle of competitive reverse transcriptase polymerase chain reaction using capillary electrophoresis and laser-induced fluorescence detection. We selected the PO ets-2 for our studies as this transcription factor was shown to be involved in neurodegenerative disease. As little as 10ng of total RNA each were extracted from 5 different regions of human postmortem brain and used in the assay system. Our results revealed that the ets-2 gene transcript was detectable at the atto-gram level in the brain (54.5 ± 17.7 ag/ 10 ng RNA in the occipital lobe, 34.2 ± 7.5 in temporal lobe, 40.2 ± 15.6 in the frontal lobe, 31.4 ± 15.7 in the cerebellum, and undetectably low in the parietal lobe). This is the first report at this sensitivity level providing neurobiology with a powerful analytical tool.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318881
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  • 2
    Electronic Resource
    Electronic Resource
    Changes in plasma taurine levels after different endurance events (1999)
    Springer
    Amino acids 16 (1999), S. 71-77 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine ; Marathon ; Endurance exercise
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The sulphonated amino acid taurine increased significantly in the plasma of trained athletes after three endurance exercises of different duration and intensity, a 90 min run on a treadmill at 75% of an individual's VO2 peak, a Marathon, 42.2km and a 100km run, by 19%, 77% and 36%, respectively. Such results indicated that the speed at which the exercise is per formed, referred to as the intensity, rather than the duration of the exercise, correlated with the elevated taurine levels possibly indicating its release from muscle fibres. The plasma amino acid pool decreased significantly in relationship with the duration of the exercise, caused by their utilisation for glucogenesis. The possible sources of the increased plasma taurine are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318886
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  • 3
    Electronic Resource
    Electronic Resource
    Synthesis of non proteinogenic dipeptides by asymmetric hydrogenation (1999)
    Springer
    Amino acids 17 (1999), S. 369-376 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Non-proteinogenic dipeptides ; Dehydrodipeptides ; Diastereoselectivity ; N-Boc-Dehydroamino acids ; Asymmetric hydrogenation ; Chiral rhodium catalysts
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary N-Boc protected non-proteinogenic dipeptides with D,L-and L,L-configuration were prepared by catalytic asymmetric hydrogenation of the corresponding dehydrophenylalanyl-(L)-phenylalanine derivatives. The configuration of the new stereogenic centre depends first of all on the catalyst configuration and is less influenced by the substrate configuration. Diastereomeric excesses in the range of 80–96% de could be increased up to 99% by recrystallization. Analytical data of selected new compounds are given.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361662
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  • 4
    Electronic Resource
    Electronic Resource
    Production of polyclonal antibodies towards the immunodetection of insecticide phosalone (1999)
    Springer
    Amino acids 17 (1999), S. 377-389 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Polyclonal antibodies ; Phosalone ; Immunodetection ; Hapten synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Hapten synthesis for the production of specific insecticide phosalone polyclonal antibodies was carried out starting from an intermediate of the phosalone synthesis, 6-chloro-2-benzoxazolone1. Two haptens containing different spacers have been prepared: N-5-carboxypentyl-6-chloro-2-benzoxazolone7 and N-(2-oxo-3-aza-5-carboxypentyl)-6-chloro-2-benzoxazolone12. Each of these two haptens conjugated to bovine serum albumine (BSA) was used to immunize four rabbits. Immunoassays of phosalone were performed with ELISA using solid-phase bound hapten thyroglobulin conjugate and horseradish peroxidase labelled goat antirabbit IgG. The more sensitive response was observed when the antiserum obtained from the rabbit immunized with the hapten-BSA conjugate containing the N-2-oxo-3-aza-5-carboxypentyl spacer was in competition with the same hapten coupled to thyroglobulin. An identical response was obtained under the same conditions when using benzoxazolone instead of phosalone as competitor, showing a good recognition of the specific aromatic part of the organophosphate insecticide phosalone. Reduction of coating conjugate concentration (from 2 to 0.05μg/well) and also the use of heterologous coating protein instead of homologous did improve the sensitivity, resulting in a concentration of phosalone required to inhibit binding by 50% of 2 mg/l and a detection limit of 0.02 mg/l.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361663
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  • 5
    Electronic Resource
    Electronic Resource
    Plasma amino acid levels after carbon tetrachloride induced acute liver damage. A dose-response and time-response study in rats (1999)
    Springer
    Amino acids 16 (1999), S. 1-11 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Liver ; Hepatic damage ; Carbon tetrachloride
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The aims of the present study were to assess the changes of individual plasma amino acid levels in relation (1) to the severity of liver damage and (2) to the process of liver recovery. Acute liver injury was induced by an intragastric administration of CCl4 diluted in olive oil in doses of 2, 4 and /or 6 g of CCl4 per kg b.w. The control rats received olive oil only. Animals were sacrificed at 16, 24, 48 and 96 hours after treatment. The severity of liver injury was assessed by histological examination, by changes in ALT and AST in the blood plasma and by changes in liver weight. Statistical analysis was carried by ANOVA, p 〈 0.05 was considered significant. The Spearman rank correlation coefficient was used as a measure of the degree of linear relationship between variable and dose. In the period of the development of acute liver damage, i.e. at 16 and 24 hours after treatment, an increase in blood plasma amino acid levels and positive correlations with the dose of CCl4 were observed for most individual amino acids. The only exception was arginine which decreased in a dose dependent manner. At a phase of liver recovery, i.e. at 48 and 96 hours after CCl4 treatment, the concentrations of some individual amino acids decreased below the control values. The negative correlation with the dose of CCl4 occurred for taurine and isoleucine (at 48 hours) and taurine, threonine, valine, methionine, isoleucine and leucine (at 96 hours).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318880
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  • 6
    Electronic Resource
    Electronic Resource
    Fatty acids and glycerol or lactate are required to induce gluconeogenesis from alanine in isolated rabbit renal cortical tubules (1999)
    Springer
    Amino acids 16 (1999), S. 41-58 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Alanine ; Fatty acids ; Glutamine and glutamate synthesis ; Glycerol and lactate metabolism ; Malate-aspartate shuttle ; Rabbit kidney-cortex tubules ; Renal gluconeogenesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In isolated rabbit renal cortical tubules, glucose synthesis from 1 mM alanine is negligible, while the amino acid is metabolized to glutamine and glutamate. The addition of 0.5 mM octanoate plus 2 mM glycerol induces incorporation of [U-14C]Alnine into glucose and decreases glutamine synthesis, whereas oleate and palmitate in the presence of glycerol are less potent than octanoate. Gluconeogenesis is also significantly accelerated when glycerol is substituted by lactate. In view of an increase in14CO2 fixation and elevation of both cytosolic and mitochondrial NADH/NAD+ ratios, the activation of glucose formation from alanine upon the addition of glycerol and octanoate is likely due to (i) stimulation of pyruvate carboxylation, (ii) increased availability of NADH for glyceraldehyde-3-phosphate dehydrogenase and (iii) elevation of mitochondrial redox state causing a diminished provision of ammonium for glutamine synthesis. The induction of gluconeogenesis in the presence of alanine, glycerol and octanoate is not related to cell volume changes. The results presented in this paper show the importance of free fatty acids and glycerol for regulation of renal gluconeogenesis from alanine. The possible physiological significance of the data is discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318884
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  • 7
    Electronic Resource
    Electronic Resource
    Substituted 4-hydroxyproline di- and tri-peptides as cytotoxic agents (1999)
    Springer
    Amino acids 16 (1999), S. 79-89 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Anti-neoplastic amino acids ; Purine and DNA synthesis inhibitors ; PRPP amido transferase and IMP dehydrogenase inhibitors
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary 4-Hydroxyproline di- and tri-peptides and N-cbz-hydroxypropylglycinamides were observed to be potent cytotoxic agents against the growth of suspended single cells, L-1210, Tmolt3, and HeLa-S3. The agents were not as potent against the growth of cultured solid tumor cells. Selected derivatives were investigated for their mode of action in Tmolt3 leukemia cells. The compounds selectively inhibited DNA synthesis at 50 and 100smM. The target site of action of the agents appeared to be the purinede novo pathway with marked inhibition of the activities of the two regulatory enzymes of the pathway, i.e. PRPP amido-transferase and IMP dehydrogenase. d[NTP] pools were reduced by the agents consistent with their overall reduction of DNA synthesis. Other marginally inhibited targets of the agents were r-RNA polymerase and TMP-kinase activities. The DNA molecule itself did not appear to be a target of these agents.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318887
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  • 8
    Electronic Resource
    Electronic Resource
    Molecular cloning and expression analyses of mitochondrial and plastidic isoforms of cysteine synthase (O-acetylserine(thiol)lyase) fromArabidopsis thaliana (1999)
    Springer
    Amino acids 16 (1999), S. 113-131 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Targeting ; Mitochondria ; Chloroplasts ; Cysteine synthase ; Transit peptide ; Transgenic plants ; Processing
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Cysteme synthase, the key enzyme for fixation of inorganic sulfide, catalyses the formation of cysteine from O-acetylserine and inorganic sulfide. Here we report the cloning of cDNAs encoding cysteine synthase isoforms fromArabidopsis thaliana. The isolated cDNA clones encode for a mitochondrial and a plastidic isoform of cysteine synthase (O-acetylserine (thiol)-lyase, EC 4.2.99.8), designated cysteine synthase C (AtCS-C, CSase C) and B (AtCS-B; CSase B), respectively.AtCS-C andAtCS-B, having lengths of 1569-bp and 1421-bp, respectively, encode polypeptides of 430 amino acids (∼45.8 kD) and of 392 amino acids (∼ 41.8 kD), respectively. The deduced amino acid sequences of the mitochondrial and plastidic isoforms exhibit high homology even with respect to the presequences. The predicted presequence of AtCS-C has a N-terminal extension of 33 amino acids when compared to the plastidic isoform. Northern blot analysis showed thatAtCS-C is higher expressed in roots than in leaves whereas the expression ofAtCS-B is stronger in leaves. Furthermore, gene expression of both genes was enhanced by sulfur limitation which in turn led to an increase in enzyme activity in crude extracts of plants. Expression of theAtCS-B gene is regulated by light. The mitochondrial, plastidic and cytosolic (Hesse and Altmann, 1995) isoforms of cysteine synthase ofArabidopsis are able to complement a cysteine synthasedeficient mutant ofEscherichia coli unable to grow on minimal medium without cysteine, indicating synthesis of functional plant proteins in the bacterium. Two lines of evidence proved thatAtCS-C encodes a mitochondrial form of cysteine synthase; first, import ofin vitro translation products derived from AtCS-C in isolated intact mitochondria and second, Western blot analysis of mitochondria isolated from transgenic tobacco plants expressing AtCS-C cDNA/c-myc DNA fusion protein.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01321531
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  • 9
    Electronic Resource
    Electronic Resource
    Unusual amino acids VIII. Asymmetric hydrogenation of some heteroaryl-N-CBZ and N-BOC aminocinnamic acid derivatives (1999)
    Springer
    Amino acids 16 (1999), S. 21-27 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Non-proteinogenic optically active amino acids ; Dehydroamino acids ; Chiral rhodium catalysts ; Asymmetric hydrogenation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary (Z)-α-[(Benzyloxy)- or (tert.-butyloxy)carbonylamino]-β (thienyl)-or (furyl)-acrylic acids and their esters were prepared by known methods and hydrogenated to the corresponding optically active alanine derivatives with optical yields in the range of 58–93% ee using the cationic rhodium complex of “PROPRAPHOS”.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318882
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  • 10
    Electronic Resource
    Electronic Resource
    Contribution of serum albumin to the transport of orally administered L-tryptophan into liver of rats with L-tryptophan depletion (1999)
    Springer
    Amino acids 16 (1999), S. 29-39 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; L-Tryptophan ; Serum albumin ; Transport ; L-Tryptophan depletion ; α-Methyl-DL-tryptophan ; Analbuminemic rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The role of serum albumin in the transport of orally administered L-tryptophan (Trp) into rat tissues was examined using analbuminemic and Sprague-Dawley (SD) rats with and without a-methyl-DL-tryptophan (AMT)-induced Trp depletion. Trp was orally administered to rats 16h after AMT or 0.85% NaCl administration, when liver tryptophan 2,3-dioxygenase and protein synthetic activities in AMT-treated rats were similar to those of 0.85% NaCl-treated rats. After oral Trp administration, regardless of the presence or absence of Trp depletion, free serum Trp concentrations were similar in the analbuminemic and SD rats, while total serum Trp concentrations were lower in analbuminemic rats than in SD rats. Although liver, brain, and muscle Trp concentrations after oral Trp administration under Trp depletion were lower in analbuminemic rats than in SD rats, the ratio of the liver Trp concentration in analbuminemic rats to that in SD rats was smaller than that of the brain or muscle Trp concentration. These results suggest that variations in serum albumin levels could affect the transport of orally administered Trp into the liver of rats with Trp depletion.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318883
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  • 11
    Electronic Resource
    Electronic Resource
    A comparison of15N proline and13C leucine for monitoring protein biosynthesis in the skin (1999)
    Springer
    Amino acids 16 (1999), S. 107-111 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Tissue protein synthesis ; Stable isotope amino acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The tracers L15N-proline and L(1-13C)-leucine were used to explore the synthesis of skin proteins in vivo in rabbits. They orally received a single dose containing an equimolecular mixture of L(1-13C)-leucine and L15N-proline. The changes in the amounts of these tracers in blood and skin were monitored for a total of 8 h. The data showed the appearance of the two tracers in blood within 15 min and their clearance in 8h. They were both rapidly (15 min) incorporated into skin proteins, but more proline was incorporated than leucine. We therefore consider L15N-proline to be a better tracer than L(1-13C)-leucine for studying protein metabolism in the skin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01321530
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  • 12
    Electronic Resource
    Electronic Resource
    Kainic acid (KA)-induced seizures in Sprague-Dawley rats and the effect of dietary taurine (TAU) supplementation or deficiency (1999)
    Springer
    Amino acids 16 (1999), S. 133-147 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine ; Kainic acid ; Epilepsy ; Anticonvulsants ; Neuroprotection ; Excitatory amino acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Male Sprague-Dawley rats received TAU supplementation (1.5% in drinking water) or TAU deficient diets for 4 weeks to test for a possible neuroprotective role of TAU in KA-induced (10 mg/kg s.c.) seizures. TAU supplementation significantly increased serum and hippocampal TAU levels, but not TAU content in temporal cortex or striatum. TAU deficient diets did not attenuate serum or tissue TAU levels. Dietary TAU supplementation failed to decrease the number or latency of partial or clonic-tonic seizures or wet dog shakes, whereas a TAU deficient diet decreased the number of clonictonic and partial seizures. This study does not support previous observations of an anticonvulsant effect of TAU against KA-induced seizures. KAtreatment decreasedα 2-adrenergic receptor binding sites and TAU content in the temporal cortex across all dietary treatment groups, supporting previous evidence of severe KA-induced damage and neuronal loss in this brain region.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01321532
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  • 13
    Electronic Resource
    Electronic Resource
    Enzymatic resolution of amino acids via ester hydrolysis (1999)
    Springer
    Amino acids 16 (1999), S. 191-213 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Enzymatic resolution ; Ester hydrolysis ; Proteases ; Lipases
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The present review outlines recent examples of enzyme-based resolution procedures for amino acids via the hydrolysis of their esters. The resolutions have been achieved by using proteases (α-chymotrypsin, subtilisin and other microbial proteases, and sulfhydryl proteases of plant origin) and lipases. Relevant work utilizing yeast and other microbial cells is also included.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388169
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  • 14
    Electronic Resource
    Electronic Resource
    Syntheses of optically active 2-amino-4-oxobutyric acid and N,O-protected derivatives (1999)
    Springer
    Amino acids 16 (1999), S. 251-272 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Unusual amino acids ; Aspartic acidβ-semialdehyde ; Aspartaldehyde ; 2-Amino-4-oxobutyric acid ; Enantioselective synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Strategies for the synthesis of optically active aspartaldehyde derivatives are reviewed. Most of them are using the chiral pool: allylglycine or naturally occurring homoserine, aspartic acid or methionme and side chain modifications. This will be developed in the first part. Some other original routes are also displayed in the second part. Different aspects of each strategy are discussed: the nature and number of steps, the problem of protecting groups, the price and availability of starting materials. Some synthetic applications of such interesting chiral synthons are shown in the last part.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388171
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  • 15
    Electronic Resource
    Electronic Resource
    Asymmetric hydrogenation of dehydrodipeptide esters bearing different protective groups (1999)
    Springer
    Amino acids 16 (1999), S. 391-401 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Dipeptide derivatives ; Non-proternogenic optically active dipeptide esters ; Dehydrodipeptides ; Chiral rhodium catalysts ; Asymmetric hydrogenation ; Diastereoselectivity
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary N-[(Z)-N-Benzoyl- orN-Boc-(2-fluorophenyl)dehydroalanyl]-(R)-or (S)-phenylalanine esters were synthesized and hydrogenated to give the corresponding dipeptide derivatives with optical yields in the range of 53–87%de using the cationic rhodium complexes of PROPRAPHOS and BPPM. The efficiency of chiral diphosphine ligands as well the effect of the chiral center in the substrate on the catalytic asymmetric induction was studied.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388178
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  • 16
    Electronic Resource
    Electronic Resource
    Spectral analysis of a series of partially protected and deprotected tetrapeptides, analogues of AS-I phytotoxin (1999)
    Springer
    Amino acids 16 (1999), S. 403-413 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Phytotoxin AS-I analogues ; FAB ; PD ; ESI mass spectrometry ; 1H,13C and 2D NMR
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A series of six tetrapeptides, analogues of AS-I phytotoxin, pathogenic to sunflower, have been synthesized either in solution and/or by solid phase methods and have been tested for phytotoxic activity in various plants and cytotoxic activity in three cancer cell lines. These peptides were identified as model compounds by fast atom bombardment (FAB), plasma desorption (PD), electrospray ionization (ESI) mass spectrometry and by1H,1H-1H,13C and1H-13C NMR. The data presented show that in protected tetrapeptides the molecular ion was easily identified whereas some difficulties appeared with the fully deprotected peptides. NMR spectra are given.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388179
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  • 17
    Electronic Resource
    Electronic Resource
    Synthesis and anti-phlogistic potency of some new non-proteinogenic amino acid conjugates of “Diclofenac” (1999)
    Springer
    Amino acids 16 (1999), S. 425-440 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Diclofenac ; Anti-phlogistics ; Non-proteinogenic amino acids ; Voltaren®. Thionation ; Cyclo-oxygenase inhibitors ; Ulcerogenic gastritis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In search for more potent, particularly less ulcerogenic gastritis that hopefully replace the universal NSAID “Diclofenac”, (2-[(2,6-di-chlorophenyl)amino]-phenylacetic acid, C.A.S. 15307-86-5), twelve new non-proteinogenic amino acid conjugates of the drug, namely that of sarcosine,β-alanine, D-leucine and D-phenylalanine, were synthesized and biologically screened for their anti-inflammatory, analgesic and ulcerogenic activity in rats. “Diclofenac” amino acid esters (IIa-d), were synthesizedvia the corresponding HOSu or HOBt active esters. Alkaline hydrolysis (NaOH) followed by acidification (KHSO4) or thioamide formation (Lawsson's Reagent, C.A.S. 19172-47-5), afforded the corresponding free acids IIIa-d or the thioamides IVa-d respectively. Interestingly, in contrary to the parent “Diclofenac”, the synthesized candidates (except IIId), were entirly nonulcerogenic in rats. Further, they considerably retained a generelized anti-phlogistic activity. The major “Diclofenac” irritating gastric side effect was thus eliminated. Particularly, the sarcosine conjugate IIa and its thiomimic IVa exhibit promising therapeutic perspectives.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388181
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  • 18
    Electronic Resource
    Electronic Resource
    Gender-related differences in polyamine oxidase activity in rat tissues (1999)
    Springer
    Amino acids 17 (1999), S. 139-148 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Polyamine oxidase ; Polyamines ; Gender ; Rat
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Variations in level of polyamines and their related enzymes are frequently observed in response to some treatments which affect in a different way male and female. The possibility of a gender-related difference in the oxidation of polyamines was investigated in rats by measuring the activity of polyamine oxidase, a ubiquitous enzyme of vertebrate tissues, which transforms spermine into spermidine and spermidine into putrescine. The study was carried out on thymus, spleen, kidney and liver of young rats of both sexes, and female rats showed a lower polyamine oxidase activity than male rats in all the tissues. We also found higher values of spermidine acetylation in female than male rats in thymus and liver. Owing to these gender-related differences, a higher spermidine N-acetyltransferase/ polyamine oxidase ratio was found in female than in male rats. A second gender-related difference was a higher spermidine/spermine ratio in female than in male, the only exception being the thymus. These basal differences possibly account for the gender-related differences of polyamine metabolic enzyme activities in response to some treatments, including drugs or hormones.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361877
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  • 19
    Electronic Resource
    Electronic Resource
    Amino acids and osmolarity in honeybee drone haemolymph (1999)
    Springer
    Amino acids 17 (1999), S. 195-205 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Apis mellifera ; Drones ; Osmolarity ; Age dependency
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In the haemolymph of honeybee drones, concentrations of free amino acids were higher than in worker haemolymph, with different relative proportions of individual amino acids. The overall concentration of free amino acids reached its highest level at the 5th day after adult drone emergence, and after the 9th day only minor changes in the concentration and distribution of free amino acids were observed. This coincides with the age when drones reach sexual maturity and change their feeding behaviour. Levels of essential free amino acids were high during the first 3 days of life and thereafter decreased. Osmolarity was lowest at emergence (334 ± 41 mOsm), increased until the age of 3 days (423 ± 32mOsm) and then stayed generally constant until the 16th day of life. Only 25-day-old drones had significantly higher osmolarity (532 ± 38 mOsm). The overall change in osmolarity during a drone's lifetime was about 40%.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361882
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  • 20
    Electronic Resource
    Electronic Resource
    Novel glutathione analogues containing the dithiol and disulfide form of the Cys-Cys dyad (1999)
    Springer
    Amino acids 17 (1999), S. 257-265 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Conformational constraint ; Cyclic disulfides ; -Cys-Cys-peptides ; Dipeptide mimetics ; Dithiols ; Glutathione analogues
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The glutathione analogue γ-(H-Glu-OH)- -OH (5), containing the 8-membered disulfide ring- replacing the native -Cys-Gly fragment, has been synthesized and characterized together with its reduced dithiol form γ-(H-Glu-OH)-Cys-Cys-OH (6).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366924
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  • 21
    Electronic Resource
    Electronic Resource
    Developmental aspects of polyamine-oxidizing enzyme activities in the mouse kidney. Effects of testosterone (1999)
    Springer
    Amino acids 17 (1999), S. 267-276 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Polyamine catabolism ; Polyamine oxidase ; Diamine oxidase ; Testosterone ; Mouse kidney
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In the present study developmental patterns of renal polyamineoxidizing enzymes polyamine oxidase (PAO) and diamine oxidase (DAO) in male and female ICR mice were demonstrated. The effects of testosterone (10μg/100g body weight) on renal PAO and DAO activities were also studied. The differences between sexes in both PAO and DAO activities were most clearly expressed in the immature kidney. At the age of 20 days PAO and DAO activities were 1.52 fold (p 〈 0.01) and 1.75 (p 〈 0.02) respectively higher in male mouse kidney than in female. Maturational processes reflected in significant increases in polyamine- oxidizing enzyme activities mainly in female mouse kidney, comparable with the gain in the kidney wet weight. Our data show that testosterone is able to influence renal PAO and DAO activities in addition to the well-known stimulation of polyamine biosynthesis. The hormonal effects were sex and age dependent. The influence of testosterone on renal PAO activity was mainly age dependent. The slight stimulation of renal PAO activity observed in 20- and 50-day old mice, 24h after testosterone administration, change with a decrease in the enzyme activity at the age of 70 days. The effects of testosterone on renal DAO activity were mainly sex dependent. Testosterone caused stimulation of DAO activity with a very close magnitude (nearly twice) in female mouse kidney, independently of the age of mice. In contrast, in male mice the hormone treatment resulted in a statistically significant increase in renal DAO activity at the age of 70 days (.1.3 fold, p 〈 0.05) only. It could be suggested that our data indicate the different contribution of renal PAO and DAO in androgen regulation of polyamine levels, depending on sex and the stage of the postnatal development.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366925
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  • 22
    Electronic Resource
    Electronic Resource
    Determination of the optical purity of threonine and hydroxyproline by capillary gas chromatography on a chiral stationary phase (1999)
    Springer
    Amino acids 17 (1999), S. 293-300 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Allohydroxyproline ; Allothreonine ; Chiral separation ; Chirasil-Val ; Hydroxyproline ; Threonine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Experimental conditions for the derivatization and resolution by GLC of all stereoisomers of threonine and 4-hydroxyproline are reported. Threonine was in two steps converted toN,O-bisisobutoxycarbonyl 2,2,2-trifluoroethyl ester derivatives, the second of which was performed under anhydrous conditions. As such the enantiomers could pairwise be separated by capillary gas chromatography on a Chirasil-Val column. SinceL- andD-threonine eluted much earlier than the corresponding allo forms, quantitative determination of the allothreonine content inD- orL-threonine down to the one percent level could be simply accomplished but also enantiomeric impurities could be determined. Unlike for threonine, the corresponding 4-hydroxyproline isomers could not all be resolved asN,O-bisisobutoxycarbonyl 2,2,2-trifluoroethyl esters on this column. Although diastereomers could still be separated, the allo pair cochromatographed and the resolution for theL- andD-isomers was low. Complete separation of the 4-hydroxyproline isomers could be accomplished asN,O-bisprotected isobutyl amides, the formation of which required three derivatization steps. These were used for the determination of allohydroxyproline.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366928
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  • 23
    Electronic Resource
    Electronic Resource
    Enhanced taurine release in cultured cerebellar granule cells in cell-damaging conditions (1999)
    Springer
    Amino acids 17 (1999), S. 323-334 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine release ; Cerebellar granule cells ; Celldamaging conditions ; Glutamate receptors ; Veratridine ; Potassium stimulation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The release of taurine from cultured cerebellar granule neurons was studied in different cell-damaging conditions, including hypoxia, hypoglycemia, ischemia, oxidative stress and in the presence of free radicals. The effects of both ionotropic and metabotropic glutamate receptor agonists on the release were likewise investigated. The release of [3H]taurine from the glutamatergic granule cells was increased by K+ (50mM) and veratridine (0.1 mM), the effect of veratridine being the greater. Hypoxia and ischemia produced an initial increase in release compared to normoxia but resulted in a diminished response to K. Hypoglycemia, oxidative stress and free radicals enhanced taurine release, and subsequent K− treatment exhibited a correspondingly greater stimulation. A common feature of taurine release in all the bove conditions was a slow response to the stimulus evoked by K+ and particularly to that evoked by veratridine. All ionotropic glutamate receptor agonists potentiated taurine release, but only the action of kainate seemed to be receptor-mediated. Metabotropic receptor agonists of group I slightly stimulated the release. The prolonged taurine release seen in both normoxia and cell-damaging conditions may be of importance in maintaining homeostasis in the cerebellum and reducing excitability for a longer period than other neuroprotective mechanisms.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361658
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  • 24
    Electronic Resource
    Electronic Resource
    Evidence that taurine modulates osmoregulation by modification of osmolarity sensor protein ENVZ — expression (1999)
    Springer
    Amino acids 17 (1999), S. 347-355 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine ; Osmoregulation ; Rat ; Osmolarity sensor protein ENVZ
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Although the involvement of taurine in osmoregulation is well-documented and widely accepted, no detailed mechanism for this function has been reported so far. We used subtractive hybridization to study mRNA steady state levels of genes up- or downregulated by taurine. Rats were fed taurine 100mg/kg body weight per day for a period of three days and hearts (total ventricular tissue) of experimental animals and controls were pooled and used for mRNA extraction. mRNAs from two groups were used for subtractive hybridization. Clones of the subtractive library were sequenced and the obtained sequences were identified by gen bank assignment. Two clones were found to contain sequences which could be assigned to the osmolarity sensor protein envZ, showing homologies of 61 and 65%. EnvZ is an inner membrane protein in bacteria, important for osmosensing and required for porine gene regulation. It undergoes autophosphorylation and subsequently phosphorylates OmpR, which in turn binds to the porin (outer membrane protein) promoters to regulate the expression of OmpF and OmpC, major outer membrane porines. This is the first report of an osmosensing mechanism in the mammalian system, which was described in bacteria only. Furthermore, we are assigning a tentative role for taurine in the osmoregulatory process by modifying the expression of the osmoregulatory sensor protein ENVZ.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361660
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  • 25
    Electronic Resource
    Electronic Resource
    Inhibitory effect of arginine-derivatives from ginseng extract and basic amino acids on protein-arginine N-methyltransferase (1999)
    Springer
    Amino acids 17 (1999), S. 391-400 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Protein ; arginine methyltransferase ; Inhibitors ; Ginseng extract ; Arginine derivatives ; Basic amino acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Protein-arginine N-methyltransferase (protein methylase I) catalyzes methylation of arginyl residues on substrate protein posttranslationally utilizing S-adenosyl-L-methionine as the methyl donor and yields NG-methylarginine residues. Arginyl-fructose and arginyl-fructosyl-glucose from Korean red ginseng were found to inhibit protein methylase I activity in vitro. This inhibitory activity was shown to be due to arginyl moiety in the molecules, rather than that of carbohydrates. Several basic amino acids as well as polyamines were also found to inhibit protein methylase I activity. Interestingly, the intensity of the inhibitory activity was correlated with the number of amino-group in polyamines, thus, in the order of spermine 〉 spermidine 〉 putrescine 〉 agmatine-sulfate, with IC50 at approximately 15 mM, 25 mM, 35 mM, and 50 mM, respectively. On the other hand, neutral amino acids or NaCI did not inhibit the enzyme activity. Lineweaver-Burk plot analysis of the protein methylase I activity in the presence of arginine and spermidine indicated that the inhibition was competitive in nature in respect to protein substrate, with the Ki values of 24.8 mM and 11.5 mM, respectively.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361664
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  • 26
    Electronic Resource
    Electronic Resource
    A new protection/activation strategy for the synthesis of naturally occurring and non-naturalα-N-alkylamino acids (1999)
    Springer
    Amino acids 16 (1999), S. 287-295 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Hexafluoroacetone ; α-N-Methylamino acids ; α-N-Phosphinoylmethylamino acids ; Pro-Glu-chimeras ; Pro-Tauchimeras
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary A new method for the preparation of N-methylamino acids and some of their derivatives starting from hexafluoroacetone protected amino acids is described. The new concept results in saving of steps compared to conventional protection/activation techniques. Protection and deprotection proceed without racemization.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388173
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  • 27
    Electronic Resource
    Electronic Resource
    Synthesis of perfluoroalkylatedβ-alanine and some peptide derivatives: An access to original surfactants (1999)
    Springer
    Amino acids 16 (1999), S. 381-389 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Perfluorinated compounds ; Surfactants ; Complexing properties ; Carnosine ; β ; Amino acids ; Blood substitutes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The reaction of amines or sodium azide with 3-perfluoroalkyl-3-fluoroprop-2-enoate, followed by hydrogenation, affords perfluoroalkylatedβ-alanine analogues in very good yields. These compounds can be linked via an amide bond to produce peptide analogues such as carnosine or carcinine derivatives, which could have surfactive and complexing properties.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388177
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  • 28
    Electronic Resource
    Electronic Resource
    Cu(III)-Polypeptide complexes exhibiting SOD-like activity (1999)
    Springer
    Amino acids 16 (1999), S. 415-423 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; SOD-like activity ; Cu (III)-Poly-L-lysine ; Cu(III)-Poly-L-glutamic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The SOD-like activity of Cu(III) -complexes with polypeptides poly-L-lysine and poly-L-glutamic acid respectively was investigated. The Cu(II)-polypeptide complexes were first oxidized by K2IrCl6 to give the corresponding Cu(III) -compounds. The oxidation of Cu(II) and the corresponding Cu(II)/Cu(III) potential was evaluated by cyclic voltammetry (c.v.), UV-Vis and EPR spectroscopic (r.t.) experiments. Spin trapping EPR spectra were also conducted to confirm the formation of the superoxide radical. The SOD-like activity of each Cu(III)-complex was proved using the nitro blue tetrazolium (NBT) method slightly modified.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388180
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  • 29
    Electronic Resource
    Electronic Resource
    Effect of some herbicides on the production of lysine byAzotobacter chroococcum (1999)
    Springer
    Amino acids 17 (1999), S. 165-173 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Lysine ; Herbicides ; Azotobacter ; Xenobiotics
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Production of lysine byAzotobacter chroococcum strain H23 was studied in chemically-defined media amended with different concentrations of alachlor, metolachlor, 2,4-D, 2,4,5-T and 2,3,6-TBA. The presence of 5, 10, and 50μg/ml of alachlor or 2,3,6-TBA significantly decreased quantitative production of lysine. However, the presence 2,4-D or 2,4,5-T at concentrations of 10 and 50μg/ml enhanced the production of lysine. Quantitative production of lysine was not affected as consequence of the addition of metolachlor to the culture medium, showing that the release lysine to the culture media byA. chroococcum was not affected by that herbicide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361879
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  • 30
    Electronic Resource
    Electronic Resource
    Synthesis and enzymology of modifiedN-benzyloxycarbonyl-L-cysteinylglycyl-3,3-dimethylaminopropylamide disulphides as alternative substrates for trypanothione reductase fromTrypanosoma crud: Part 3 (1999)
    Springer
    Amino acids 17 (1999), S. 175-183 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Trypanothione ; Glutathione ; Benzyloxycarbonyl-reductase ; Hydrocinnamoyl
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Kinetic data for alternative substrates of recombinant trypanothione reductase fromTrypanosoma cruzi were measured for a series ofN-substituted-L-cysteinylglycyl-3-dimethylaminopropylamides, in which the cysteineN-substituent was either a variant of the benzyloxycarbonyl group or was L-phenylalanine or L-tryptophan. Replacing the benzylic ether oxygen atom by CH2. or NH had relatively minor effects on kcat, but raised the value of Km, 4.5- and 10-fold, respectively. Similarly, relative to the carbobenzoxy group, anN-L-phenylalanyl orN-L-tryptophanyl replacement on the cysteine hardly altered kcat, but increased Km, values by 16.6 and 7.4 fold, respectively. These observations were consistent with the Km, values referring primarily to binding for this series of nonspecific substrates.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361880
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  • 31
    Electronic Resource
    Electronic Resource
    Ion permeation properties of a cloned human 5-HT3 receptor transiently expressed in HEK 293 cells (1999)
    Springer
    Amino acids 17 (1999), S. 243-255 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Serotonin receptor ; Serotonin-3 receptor ; Ion channel ; Ion permeability
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Human 5-HT3 receptors expressed in HEK 293 cells were studied using patch-clamp techniques. The permeability ratios of cations to Na+ were Li+, 1.16; K+, 1.04; Rb+, 1.11; Cs+ 1.11; NMDG+, 0.04; Ca2+, 0.49, and Mg2+, 0.37. The permeability sequence of the alkali metal cations was Li+ 〉 Rb+ = Cs+ 〉 K+ 〉 Na+. Increased external concentrations of Ca2+ or Mg2+ decreased 5-HT-induced currents at all potentials tested in a voltage-independent manner. The single-channel conductance of human 5-HT3 receptors measured by fluctuation analysis of whole-cell currents was 790 ± 100fS. Differences in the basic properties of 5-HT3 receptors between species may explain interspecies differences in pharmacological properties.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366923
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  • 32
    Electronic Resource
    Electronic Resource
    Taurine modulates expression of transporters in rat brain and heart (1999)
    Springer
    Amino acids 17 (1999), S. 301-313 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine ; Transporter ; Rat ; Brain ; Heart
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In pro- and eucaryotic life, cellular and subcellular compartments are separated by membranes and the regulated and selective passage of specific molecules across these membranes is a basic and highly conserved principle. We were interested whether taurine, a naturally occuring amino acid, would be able to induce or suppress expression of transporters with the Rationale that taurine was shown to detoxify a series of endogenous toxins and xenobiotics of various chemically non-related structures. For this purpose we used a gene hunting technique, subtractive hybridization, subtracting mRNAs of taurine-treated rat brain and heart from untreated controls. Subtracted mRNAs were then converted to cDNAs, amplified, sequenced and identified by gene bank data. We found five transporter transcripts, the phosphonate transport ATPase PHNC, multidrug transporter homolog MTH104, protein-exportmembrane protein SECD, oligopeptide transporters oppA and oppD, in the brain and two: ABC-transporter BRAF-2 and cation-transport ATPase PACS, in the heart. Homologies of the sequences found were in any case 〉50% thus permitting the identification of transporters with high probability. The biological meaning could be that a naturally occuring amino acid, taurine, modulates complex transport systems. The most prominent finding is the upregulation of a multidrug transporter transcript, explaining a mechanism for the nonselective detoxifying action of taurine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366929
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  • 33
    Electronic Resource
    Electronic Resource
    Production of tyrosine and other aromatic compounds from phenylalanine by rumen microorganisms (1999)
    Springer
    Amino acids 17 (1999), S. 335-346 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Tyrosine ; Phenylalanine ; Aromatic compounds ; Rumen microorganisms[/klw]
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Rumen contents from three fistulated Japanese native goats fed Lucerne hay cubes (Medicago sativa) and concentrate mixture were collected to prepare the suspensions of mixed rumen bacteria (B), mixed protozoa (P) and a combination of the two (BP). Microbial suspensions were anaerobically incubated at 39°C for 12h with or without 1 MM ofl-phenylalanine (Phe). Phe, tyrosine (Tyr) and other related compounds in both supernatant and microbial hydrolysates of the incubations were analyzed by HPLC. Tyr can be produced from Phe not only by rumen bacteria but also by rumen protozoa. The production of Tyr during 12h incubation in B (183.6 μmol/g MN) was 4.3 times higher than that in P. One of the intermediate products between Phe and Tyr seems to bep-hydroxyphenylacetic acid. The rate of the net degradation of Phe incubation in B (76.O μmol/g MN/h) was 2.4 times higher than in P. In the case of all rumen microorganisms, degraded Phe was mainly (〉53%) converted into phenylacetic acid. The production of benzoic acid was higher in P than in B suspensions. Small amount of phenylpyruvic acid was produced from Phe by both rumen bacteria and protozoa, but phenylpropionic acid and phenyllactic acid were produced only by rumen bacteria.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361659
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  • 34
    Electronic Resource
    Electronic Resource
    Antimicrobial activity ofo-carboranylalanine (1999)
    Springer
    Amino acids 17 (1999), S. 357-368 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; o-Carboranylalanine ; Histidine ; Bacteria ; Fungi ; Oomycota ; Plasmopara
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Functionalized polyhedral carboranes, including amino acid analogs, have unique physicochemical properties and are used as experimental anticancer agents. However, our current knowledge on their effect in nonmammalian biological systems is limited. We investigated the activity spectrumin vitro ofo-carboranylalanine (o-Cba), considered to be a highly lipophilic analog of phenylalanine, against representative plant pathogenic bacteria and fungi of various taxonomic position. The antibacterial effect ofo-Cba against some species was comparable to that of the widely used agricultural antibiotic, streptomycin. The sensitivity of individual bacterial species too-Cba within the same genus varied to a greater extent than the average sensitivity of various genera. In general, this carborane-containing amino acid was more toxic to Gram positive bacteria (Bacillus, Corynebacterium, Curtobacterium, Micrococcus, Rhodococcus, and Staphylococcus) than to Gram negative ones (Agrobacterium, Erwinia, Escherichia, Pseudomonas, Rhizobium, and Xanthomonas). Compared to the commercial fungicide, prochloraz,o-Cba was weakly toxic against various fungi (Zygo- and Ascomycota). It was also inferior to the commercial fungicide metalaxyl in inhibiting the vegetative growth of oomyceteous plant pathogens (Pythium irregulare, Phytophthora cryptogea and Plasmopara halstedii). Against the asexual spores of P. halstedii,o-Cba, however, was over a thousandfold more active than tridemorph, a selective zoospore inhibitor fungicide. For all taxonomic groups, the observed antimicrobial effect ofo-Cba could be diminished with histidine, but not with phenylalanine. In studies on healthy and mildew-infected sunflower and tobacco plantso-Cba showed neither fungicidal nor phytotoxic effects at 500ppm. This is the first report on the biological activity spectrum of a carborane-containing amino acid.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361661
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  • 35
    Electronic Resource
    Electronic Resource
    Where does indolylacrylic acid come from (1999)
    Springer
    Amino acids 17 (1999), S. 401-413 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Indolylacrylic acid ; Tryptophan ; Indolylacryloylglycine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In addition to the main catabolic routes of tryptophan (Trp), there exist minor and less thoroughly investigated pathways; one of these leads to indolylacrylic acid (IAcrA). IAcrA is a plant growth hormone, whereas its biological role in animals is still obscure, as is the way and site where it is formed in the organism. A two-stage production is likely: Intestinal microorganisms catabolize Trp to indole derivatives which are then absorbed and converted to IAcrA and its glycine conjugate, indolylacryloylglyeine (IAcrGly). Our finding of IAcrGly in the urine of proven germ-free piglets points to the possibility that Trp can be converted to IAcrA without the intervention of intestinal microorganisms. Seasonal and age variations, influence of light and connection with photodermatoses have been reported. Besides other pathological conditions the differences in IAcrGly excretion relative to normal controls were especially pronounced in some myopathies, namely in boys with Duchenne muscular dystrophy.
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    URL: http://dx.doi.org/10.1007/BF01361665
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  • 36
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    Electronic Resource
    Variation in competitive abilities of plants and microbes for specific amino acids (1999)
    Springer
    Biology and fertility of soils 29 (1999), S. 257-261 
    Details
    ISSN: 1432-0789
    Keywords: Key words Alpine nitrogen cycle ; Amino acids ; Kobresia myosuroides ; Organic nitrogen ; Plant-microbe competition
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Geosciences , Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract  Microbes are assumed to possess strong competitive advantages over plants for uptake of nutrients from the soil. The finding that non-mycorrhizal plants can obtain a significant fraction of their N requirement from soil amino acids contradicts this assumption. The amino acid glycine (Gly) has been used as a model amino acid in many recent studies. Our preliminary studies showed that Gly was a poor substrate for microbial growth compared to other amino acids. We tested the hypothesis that the alpine sedge Kobresia myosuroides competes better for Gly than for other amino acids because of decreased microbial demand for this compound. Soil microbial populations that could grow using Gly as a sole carbon source were about 5 times lower than those that could grow on glutamate (Glu). Gly supported a significantly lower population than any of the ten other amino acids tested except serine. In contrast, K. myosuroides took up Gly from hydroponic solution at faster rates than Glu. In plant-soil microcosms, plants competed with soil microbes 3.25 times better for Gly than for Glu. We conclude that the low microbial demand and the rapid plant uptake of Gly relative to other amino acids allow Gly to be an especially important nitrogen source for K. myosuroides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s003740050550
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  • 37
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    Electronic Resource
    Development of chemical and sensory characteristics during enzymatic hydrolysis of soy (1999)
    Springer
    Zeitschrift für Lebensmittel-Untersuchung und -Forschung 208 (1999), S. 50-56 
    Details
    ISSN: 1431-4630
    Keywords: Key words Flavor enhancer ; Savory flavoring ; Taste ; Amino acids ; Partial least squares regression
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract  Enzymatically hydrolyzed vegetable protein was produced from soy protein using hydrolysis times of 0–20 h. The development of sensory properties and the pattern of protein degradation was followed. Around two-thirds of the final amount of free amino acids and degree of hydrolysis (DH) were achieved during the first 4 h of hydrolysis. Between 6 h and 10 h of hydrolysis the bouillon-like tastes increased significantly (P〈0.001). In this time interval the amount of free amino acids exceeded 40% of the total amino acids and the DH exceeded 50% of the theoretically possible (100%). Using partial least squares regression with standardisation of free amino acid data according to their taste threshold values showed that free glutamic acid, aspartic acid and lysine correlated with the bouillon-like tastes. By standardisation of free amino acid data with respect to their SD the specificity of the enzymes for amino acid side-chains could be seen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002170050374
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    Electronic Resource
    The influence of maturation on flavor and chemical composition of hydrolyzed soy protein produced by acidic and enzymatic hydrolysis (1999)
    Springer
    Zeitschrift für Lebensmittel-Untersuchung und -Forschung 208 (1999), S. 355-361 
    Details
    ISSN: 1431-4630
    Keywords: Key words Flavor enhancer ; Taste ; Amino acids ; Carbohydrates ; Maillard reaction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract  Hydrolyzed vegetable protein produced using hydrochloric acid (HVP) or proteolytic enzymes (EVP) was given a maturation period of up to 6 weeks at 30  °C. The maturation resulted in a darker color for both hydrolysates, but the sensory profiles were not altered to any great extent. For both hydrolysates a decrease in the amount of free amino acids or an increase in the amount of bound amino acids was seen, and for EVP, a decrease in the amount of free monosaccharides was likewise observed. In HVP the mono- and polysaccharides were destroyed during hydrolysis. The changes in amino acids could be due to, for example, a reversible binding to either a monosaccharide in EVP or a degradation product of carbohydrates in HVP, leading to the first stage of the Maillard reaction. These early reactions did not proceed to any flavor-giving Maillard reaction compounds. Maturation can therefore not be used to enhance the flavor of protein hydrolysates under the applied production conditions.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002170050429
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  • 39
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    Electronic Resource
    Effects of GABA-transaminase inhibition on brain metabolism and amino-acid compartmentation: an in vivo study by 2D 1H-NMR spectroscopy coupled with microdialysis (1999)
    Springer
    Experimental brain research 127 (1999), S. 321-327 
    Details
    ISSN: 1432-1106
    Keywords: Key words Gabaculine ; NMR spectroscopy ; Microdialysis ; Amino acids ; Compartmentation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract  The aim of this work was to study the neurochemical effects in the brain of GABA-transaminase inhibition by systemic administration of gabaculine (100 mg/kg, i.a.) in the rat. In order to investigate neurotransmitter and related amino-acid compartmentation and metabolism, we have developed an original tool: the coupling, in vivo, on the same animal, of 2D COSY 1H-NMR spectroscopy with intracerebral microdialysis. The main result is a continuous increase in GABA levels, both in the intracellular compartment (up to 3000±450%; P〈0.001) and extracellular compartment (up to 808±82%; P〈0.01) at the sixth hour. The intracellular increase in GABA level became significant at the first hour following gabaculine administration, whereas the extracellular level increased as of the second hour, probably indicating that accumulation of GABA in nerve endings precedes its release in synaptic clefts. Moreover, the levels of the excitatory amino acids, glutamate and aspartate, were decreased both in the intra- and extracellular compartments, thus enhancing sedative effects of the drug. We also observed a decrease in the global energetic creatine-phosphocreatine pool, which also could be related to the sedative properties of gabaculine, measurable by the diminution of cortical electrical activity and mean arterial blood pressure. Finally, the coupling between 2D 1H-NMR spectroscopy and intracerebral microdialysis appears to be an original tool for investigating the cerebral metabolic effects induced by pharmacological agents, in situ, in living animals.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002210050802
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    Electronic Resource
    Electronic Resource
    A food web analysis of the juvenile blue crab, Callinectes sapidus, using stable isotopes in whole animals and individual amino acids (1999)
    Springer
    Oecologia 120 (1999), S. 416-426 
    Details
    ISSN: 1432-1939
    Keywords: Key words Estuarine food web ; Stable isotopes ; Amino acids ; Growth experiment ; Crustacean metabolism
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The stable isotope compositions (C and N) of plants and animals of a marsh dominated by Spartina alterniflora in the Delaware Estuary were determined. The study focused on the juvenile stage of the Atlantic blue crab, Callinectes sapidus, and the importance of marsh-derived diets in supporting growth during this stage. Laboratory growth experiments and field data indicated that early juvenile blue crabs living in the Delaware Bay habitat fed primarily on zooplankton, while marsh-dwelling crabs, which were enriched in 13C relative to bay juveniles, utilized marsh-derived carbon for growth. In laboratory experiments, the degree to which juvenile blue crabs isotopically fractionated dietary nitrogen, as well as the growth rate, depended on the protein quality of the diet. The range of δ13C of amino acids in laboratory-reared crabs and their diets was almost 20‰, similar to the isotopic range of amino acids of other organisms. In laboratory studies, the δ13C of nonessential and essential amino acids in the diet were compared to those in juvenile crabs. Isotopic fractionation at the molecular level depended on diet quality and the crabs' physiological requirements. Comparison of whole-animal isotope data with individual amino acid C isotope measurements of wild juvenile blue crabs from the bay and marsh suggested a different source of total dietary carbon, yet a shared protein component, such as zooplankton.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004420050874
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  • 41
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    Electronic Resource
    Effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on liver phosphoenolpyruvate carboxykinase (PEPCK) activity, glucose homeostasis and plasma amino acid concentrations in the most TCDD-susceptible and the most TCDD-resistant rat strains (1999)
    Springer
    Archives of toxicology 73 (1999), S. 323-336 
    Details
    ISSN: 1432-0738
    Keywords: Key words 2 ; 3 ; 7 ; 8-Tetrachlorodibenzo-p-dioxin ; TCDD ; Phosphoenolpyruvate carboxykinase ; PEPCK ; Glucose ; Glycogen ; Amino acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract Reduced gluconeogenesis due to decreased activity of key gluconeogenic enzymes in liver, together with feed refusal, has been suggested to play an important role in 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD)-induced lethality in rats. This study was carried out to further analyse the toxicological significance of reduced gluconeogenesis by comparing dose-responses and time-courses of effects of TCDD on the activity of phosphoenolpyruvate carboxykinase (PEPCK) in liver, liver glycogen concentration as well as plasma concentrations of glucose and amino acids in both genders of TCDD-sensitive Long-Evans (L-E) rats and TCDD-resistant Han/Wistar (H/W) rats. A dose-dependent decrease in PEPCK activity was observed in H/W rats, but in L-E rats the activity was not decreased. However, TCDD impaired the strong increase in liver PEPCK activity observed in pair-fed controls of the L-E strain. Liver glycogen concentrations were severely decreased in L-E rats and moderately in H/W rats. This effect seems to be secondary to reduced feed intake, since a similar decrease was seen in pair-fed controls. Decreases in plasma glucose concentrations were also more profound in L-E rats than in H/W rats, but pair-fed controls were generally less affected. Circulating concentrations of amino acids were markedly increased in TCDD-treated L-E rats, which is likely to reflect increased mobilization of amino acids and their decreased metabolism in liver. Reduction of liver PEPCK activity cannot account for the sensitivity difference of these two strains of rats in terms of mortality. Nevertheless, the response of both strains of TCDD-treated rats regarding gluconeogenesis is different from that seen in pair-fed controls and suggesting that impairment of this pathway contributes to the development of the wasting syndrome.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002040050626
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  • 42
    Electronic Resource
    Electronic Resource
    Terfenadine induces toxicity in cultured cerebellar neurons: A role for glutamate receptors (1999)
    Springer
    Amino acids 16 (1999), S. 59-70 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Cerebellar granule cells ; Neurotoxicity ; Terfenadine ; Excitatory amino acids ; Histamine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Exposure of cultured cerebellar neurons to the histamine H1 receptor antagonist terfenadine resulted in neuronal degeneration and death. Terfenadine neurotoxicity was dependent upon concentration and time of exposure. After 2h exposure, 20µM terfenadine reduced the number of surviving neurons by 75%, and as low as 10nM terfenadine induced significant neurotoxicity after 5 days of exposure. Neuronal sensitivity to terfenadine changed with age in culture, and at 25 days in culture neurons appeared to be much less sensitive than at 5 or 9–17 days in culture. Neurotoxicity by terfenadine could not be prevented by high concentrations of histamine (5 mM), but it was significantly delayed by blocking NMDA or non-NMDA glutamate receptors with MK-801 or CNQX respectively, suggesting the involvement of excitatory transmission mediated by glutamate in the neurotoxicity induced by terfenadine in these neurons. We also found that the presence of terfenadine (5,µM) unveiled the potential excitotoxicity of the non-NMDA receptor agonist AMPA (100µM), and reduced the concentration of glutamate necessary to induce excitotoxicity, compared to untreated cultures. These results suggest a role for terfenadine in the modulation of the excitotoxic response mediated in cerebellar neurons through ionotropic glutamate receptors.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318885
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  • 43
    Electronic Resource
    Electronic Resource
    Structural organization of the human eukaryotic initiation factor 5A precursor and its site-directed variant Lys50 → Arg (1999)
    Springer
    Amino acids 16 (1999), S. 91-106 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; eIF-5A ; Hypusine ; Protein folding ; Posttranslational modification
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The molecular properties of the human eukaryotic initiation factor 5A precursor and its site directed Lys50 → Arg variant have been investigated and compared. Structure perturbation methods were used to gain information about the protein architecture in solution. Intrinsic and extrinsic spectroscopic probes strategically located in the protein matrix detected the independent unfolding of two molecular regions. Three cystemes out of four were titrated in the native protein and the peculiar presence of a tyrosinate band at neutral pH was detected. At alkaline pH only two tyrosines out of three were titratable in the native protein, with an apparent pK of about 9.9. Native protein and its Lys50 → Arg variant reacted in a similar fashion to guanidine and to pH variation, but differently to thermal stress. The complex thermal unfolding of both proteins indicated the presence of intermediates. Spectroscopic data showed that these intermediates are differently structured. Consequently, the two proteins seem to have different unfolding pathways.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01318888
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  • 44
    Electronic Resource
    Electronic Resource
    Renal handling of amino acids in 5/6-nephrectomized rats: Stimulation of renal amino acid reabsorption after treatment with triiodothyronine or dexamethasone under amino acid load (1999)
    Springer
    Amino acids 16 (1999), S. 149-164 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; 5/6 nephrectomy ; Renal failure ; Amino acid transport ; Kidney ; Triiodothyronine ; Dexamethasone ; Amino acid load ; Rats
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In anaesthetized adult female rats, the renal amino acid handling was measured six days after 5/6 nephrectomy (5/6NX). The distinct rise in blood urea nitrogen as well as the significant reduction in urine flow and GFR indicate an impairment of kidney function. In principle, in 5/6NX rats amino acid plasma concentrations were comparable to those of control animals with two intact kidneys, whereas the fractional excretions (FEAA) of most endogenous amino acids measured were significantly enhanced. After bolus injection of leucine or taurine (each 20 mg/100 g b.wt.) or glutamine (90 mg/ 100 g b.wt.), dissolved in 2m1 normal saline per 100 g b.wt., the FEAA of both the amino acids administered and the endogenous amino acids increased as a sign of overloaded amino acid reabsorption capacity. This effect was more pronounced in 5/6NX rats than in controls. As early as one hour after amino acid load, plasma concentrations and FEAA returned to baseline values of 5/6NX rats. A pretreatment with triiodothyronine (20,µg/100 g b.wt.) or dexamethasone (60 µg/100 g b.wt.), both given intraperitoneally once daily for 3 days, stimulated the renal amino acid transport capacity in 5/6NX rats: the increase in FEAA after amino acid load was significantly lower compared to non-pretreatred animals. This stimulation could be shown for the bolus amino acids and the endogenous amino acids and was more distinct in 5/6NX rats than in controls with two intact kidneys.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01321533
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  • 45
    Electronic Resource
    Electronic Resource
    Nitric oxide mediates either proliferation or cell death in cardiomyocytes. Involvement of polyamines (1999)
    Springer
    Amino acids 16 (1999), S. 181-190 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Nitric oxide ; Ornithine decarboxylase ; Proliferation ; Cell death ; Cardiomyocytes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Nitric oxide (NO) is a molecule involved in several signal transduction pathways leading either to proliferation or to cell death. Induction of ornithine decarboxylase (ODC), the key enzyme of polyamine biosynthesis, represents an early event preceding DNA synthesis. In some cell types increased ODC activity seems to be involved in cytotoxic response. We investigated the role of NO and ODC induction on the events linked to cell proliferation or to cell death in cultured chick embryo cardiomyocytes. Exposure of cardiomyocytes to tumor necrosis factor (TNF) and lipopolysaccharide (LPS) caused NO synthase (NOS) and ODC induction as well as increased incorporation of [3H]-thymidine. This last effect was blocked by a NOS inhibitor and was strongly reduced by difluoromethylornithine (DFMO), an irreversible inhibitor of ODC. Sodium nitroprusside (SNP), an exogenous NO donor, inhibited the increases of NOS and ODC activities and abolished the mitogenic effect of TNF and LPS. Moreover, SNP alone caused cell death in a dose dependent manner. The cytotoxicity of SNP was not affected by DFMO while it was prevented by antioxidants. The results suggest that different pathways would mediate the response of cardiomyocytes to NO: they can lead either to ODC induction and DNA synthesis when NO is formed through NOS induction or to growth inhibition and cell death, when NO is supplied as NO donor. Increased polyamine biosynthesis would mediate the proliferative response of NO, while the cytotoxicity of exogenous NO seems to involve some oxidative reactions and to depend on the balance between NO availability and cellular redox mechanisms.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01321535
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  • 46
    Electronic Resource
    Electronic Resource
    Asymmetric syntheses of pipecolic acid and derivatives (1999)
    Springer
    Amino acids 16 (1999), S. 297-320 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Pipecolic acid ; Pipecolic acid derivatives ; Asymmetric synthesis ; Hemisyntheses ; Chiral auxiliaries
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Results in the field of asymmetric synthesis of pipecolic acid derivatives are reviewed. Three sections describe the asymmetric syntheses of the title compounds (i) from the chiral pool (α-amino acids or carbohydrates) (ii) using a chiral auxiliary either derived from terpenes,α-amino acids, tartaric acid, an amine orβ-amino alcohols (iii) by means of asymmetric catalysis.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388174
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  • 47
    Electronic Resource
    Electronic Resource
    Fromβ-lactams toα- andβ-amino acid derived peptides (1999)
    Springer
    Amino acids 16 (1999), S. 321-343 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Amino alcohols ; β-Lactams ; NCA ; Peptides ; Synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The potential ofβ-lactams as intermediates for the access toα- andβ-amino acid-derived peptides is shortly reviewed, with major focus on the technologies developed in our group. The two general strategies lie, on one side, in the oxidative ring expansion of 3-hydroxyβ-lactams toN-carboxyα-amino acid anhydrides or Leuch's anhydrides and subsequent coupling withα-amino acid esters and, on the other side, in the nucleophilic ring opening ofN-Boc-β-lactams. Both approaches have been successfully applied to the synthesis ofα,β-diamino acid,α-amino-β-hydroxy acid, polyhydroxylatedα-amino acid,α,α-disubstitutedα-amino acid,β-amino acid,β-amino-α-hydroxy acid andβ,β-disubstitutedβ-amino acid derived peptides. Because of the mild reaction conditions needed for the above transformations and the highly stereoselective procedures employed for the construction of the startingβ-lactam ring, the whole process allows the production of optically pure final products.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01388175
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  • 48
    Electronic Resource
    Electronic Resource
    Clonidine action in spontaneously hypertensive rats (SHR) depends on the GABAergic system function (1999)
    Springer
    Amino acids 17 (1999), S. 131-138 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Clonidine ; GABAA receptor antagonists ; GABA turnover ; SHR ; WKY rats
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The effect of γ-aminobutyric acid (GABA)A antagonists (bicuculline, picrotoxin) on clonidine hypotension in spontaneously hypertensive (SHR) and Wistar Kyoto (WKY) rats were examined. The GABA turnover changes after clonidine injection in both strains were also studied. Administration of clonidine alone induced the stronger decrease of systolic blood pressure (SBP) in SHR. Co-dosage of clonidine with these agents reduced its hypotensive effect in dose dependent manner and the effectiveness of both antagonists was higher in SHR. We find that clonidine stimulates GABA synthesis in the hypothalamus and the pons-medulla in both strains but the GABA turnover rate is significantly slower in SHR. Therefore, the differences in inhibitory action of GABAA receptor anatgonists between WKY and SHR rats may be explained by central GABAergic system dysfunction in the hypertension. Our results indicate that the down regulation of the GABAergic system observed in hypertension may be compensated by the action of clonidine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361876
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  • 49
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    Electronic Resource
    Utilization ofd-amino acids byFusobacterium nucleatum andFusobacterium varium (1999)
    Springer
    Amino acids 17 (1999), S. 185-193 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Anaerobic bacteria ; Catabolism ; HPLC ; Stereochemistry
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The utilization ofd- andl -amino acids with acidic, basic or polar side chains was demonstrated by HPLC. Two species of the anaerobeFusobacterium utilized D-lysine and the L isomers of glutamate, glutamine, histidine, lysine and serine. OnlyF. varium usedl-arginine,d-glutamate andd-serine as substrates, whereasF. nucleatum specifically utilizedd-histidine andd-glutamine.d-Glutamate accumulated in F. nucleatum cultures supplemented withd-glutamine, and ornithine was detected when eitherdl- orl-arginine was included inF. varium cultures. Based on literature precedents,d-glutamate andd-histidine are isomerized to their L isomers prior to degradation, but separate catabolic pathways are possible for each enantiomer of lysine and serine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01361881
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  • 50
    Electronic Resource
    Electronic Resource
    Glutamine and the immune system (1999)
    Springer
    Amino acids 17 (1999), S. 227-241 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Glutamine ; Lymphocyte ; Macrophage ; Mononuclear cell ; Cytokine ; Infection
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Glutamine is utilised at a high rate by cells of the immune system in culture and is required to support optimal lymphocyte proliferation and production of cytokines by lymphocytes and macrophages. Macrophage-mediated phagocytosis is influenced by glutamine availability. Hydrolysable glutamine dipeptides can substitute for glutamine to support in vitro lymphocyte and macrophage functions. In man plasma and skeletal muscle glutamine levels are lowered by sepsis, injury, burns, surgery and endurance exercise and in the overtrained athlete. The lowered plasma glutamine concentrations are most likely the result of demand for glutaminne (by the liver, kidney, gut and immune system) exceeding the supply (from the diet and from muscle). It has been suggested that the lowered plasma glutamine concentration contributes, at least in part, to the immunosuppression which accompanies such situations. Animal studies have shown that inclusion of glutamine in the diet increases survival to a bacterial challenge. Glutamine or its precursors has been provided, usually by the parenteral route, to patients following surgery, radiation treatment or bone marrow transplantation or suffering from injury. In most cases the intention was not to stimulate the immune system but rather to maintain nitrogen balance, muscle mass and/or gut integrity. Nevertheless, the maintenance of plasma glutamine concentrations in such a group of patients very much at risk of immunosuppression has the added benefit of maintaining immune function. Indeed, the provision of glutamine to patients following bone marrow transplantation resulted in a lower level of infection and a shorter stay in hospital than for patients receiving glutamine-free parenteral nutrition.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366922
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    Electronic Resource
    Alteration in the D-amino acid content of the rat pineal gland under anesthesia (1999)
    Springer
    Amino acids 17 (1999), S. 277-283 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; D-Aspartic acid ; D-Leucine ; Pineal gland ; Sympathetic nervous system ; Anesthesia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary In a previous report (Hamase, K. et al., Biochim Biophys Acta 1134: 214–222 (1997)), we showed that the rat pineal gland contains D-leucine (D-Leu) as well as D-aspartic acid (D-Asp). In this communication we report alterations in the content of these D-amino acids during anesthesia. The D-Asp content was significantly increased from 2.8 to 5.0, 4.8 and 5.8 nmol/pineal gland by administration of ether, urethane and pentobarbital, respectively. In contrast, the D-Leu content was decreased by administration of urethane or pentobarbital. The D-Leu content decreased from 4.2 to 2.2 pmol/pineal gland 4 hours after administration of urethane, although the content remained unchanged until 1.5 hours after administration. The content of the L-enantiomers of these amino acids were not affected by anesthesia. The urethane-induced decrease in D-leucine content was almost completely suppressed by aβ-agonist, (-)-isoproterenol, whereas the agonist itself had no effect.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366926
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  • 52
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    Electronic Resource
    Urine glycyl-L-proline increase and skin trophicity (1999)
    Springer
    Amino acids 17 (1999), S. 315-322 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Glycyl-L-proline ; Urine ; Trophicity ; Collagen
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary Glycyl-L-proline (gly-pro) is an end product of collagen metabolism that is further cleaved by prolidase (EC 3.4.13.9); the resulting proline molecules are recycled into collagen or other proteins. We postulated a relationship between defective gly-pro hydrolysis, increased collagen degradation and skin destruction. This relationship was tested using HPLC to measure the gly-pro in urine. 24 hour urine samples were collected from 27 old people (86 ± 6 years old), of whom 15 were suffering from skin pressure sores of the sacrum or calcaneus. The urine from patients with pressure sores contained significantly more gly-pro than the urine from the control. A cut-off at 7μmol/ mmol creatinine gave the test a positive predictive value of 70%. Collagen breakdown was also increased as indicated by the increase of hydroxyproline (hyp) in the urine. But this breakdown seemed to stop at the gly-pro step.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01366930
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  • 53
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    Electronic Resource
    Involvement of metabotropic glutamate receptors in taurine release in the adult and developing mouse hippocampus (1999)
    Springer
    Amino acids 16 (1999), S. 165-179 
    Details
    ISSN: 1438-2199
    Keywords: Amino acids ; Taurine release ; Metabotropic glutamate receptors ; Hippocampal slices ; Adult ; Developing mice
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Summary The inhibitory amino acid taurine has been held to function as an osmoregulator and modulator of neural activity, being particularly important in the immature brain. lonotropic glutamate receptor agonists are known markedly to potentiate taurine release. The effects of different metabotropic glutamate receptor (mGluR) agonists and antagonists on the basal and K+-stimulated release of [3H]taurine from hippocampal slices from 3-month-old (adult) and 7-day-old mice were now investigated using a superfusion system. Of group I metabotropic glutamate receptor agonists, quisqualate potentiated basal taurine release in both age groups, more markedly in the immature hippocampus. This action was not antagonized by the specific antagonists of group I but by 6-cyano-7-nitroquinoxaline-2,3-dione (CNQX) and 6-nitro-7-sulphamoylbenzo[f]quinoxaline-2,3-dione (NBQX), which would suggest an involvement of ionotropic glutamate receptors. (S)-3,5-dihydroxyphenylglycine (DHPG) potentiated the basal release by a receptor-mediated mechanism in the immature hippocampus. The group II agonist (2S, 2′R, 3′R)-2-(2′,3′-dicarboxycyclopropyl)glycine (DCG IV) markedly potentiated basal taurine release at both ages. These effects were antagonized by dizocilpine, indicating again the participation of ionotropic receptors. Group III agonists slightly potentiated basal taurine release, as did several antagonists of the three metabotropic receptor groups. Potassium-stimulated (50 mM K+) taurine release was generally significantly reduced by mGluR agents, mainly by group I and II compounds. This may be harmful to neurons in hyperexcitatory states. On the other hand, the potentiation by mGluRs of basal taurine release, particularly in the immature hippocampus, together with the earlier demonstrated pronounced enhancement by activation of ionotropic glutamate receptors, may protect neurons against excitotoxicity.
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    URL: http://dx.doi.org/10.1007/BF01321534
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  • 54
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    Electronic Resource
    Amino acids in rinse effluents as a predictor of graft function after transplantation of fatty livers in rats (1999)
    Springer
    Transplant international 12 (1999), S. 168-175 
    Details
    ISSN: 1432-2277
    Keywords: Key words Liver transplantation ; Survival ; Amino acids ; Organ preservation ; Primary nonfunction
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract There are too few reliable markers by which one can predict future function of a liver before implantation. Consequently, the purpose of this study was to test the hypothesis that amino acids in rinse–effluents could predict transplant outcome in marginal fatty livers from rats. Amino acids were measured in the rinse effluent from the livers immediately after harvest and graft preparation or cold storage. Amino acids in the effluent were twice as high in ethanol-treated animals compared to those in nonfatty controls. Ethanol-treated fatty livers survived for no longer than 7 days after transplantation while 83 % of nonfatty controls survived (P 〈 0.05). In subsequent studies, the cold-storage time was decreased to 6 h to determine whether failing fatty livers released more amino acid than grafts that would function normally. There was a significant increase in amino acids in the effluent of fatty grafts compared to controls. Moreover, the sum of the four selected amino acids (alanine, valine, histidine, leucine) was lower than 23 nmol/g liver in functional livers, whereas failing grafts had totals significantly higher than 25 nmol/g liver. The sum of the four amino acids correlated well with 24 h post-transplant serum AST levels (r = 0.78, P 〈 0.0001). So we can conclude that amino acid release can serve as a useful marker of graft viability and reliably predicts survival.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s001470050206
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    Electronic Resource
    Prediction of solvent accessibility of amino acid residues: critical aspects (1999)
    Springer
    Theoretical chemistry accounts 101 (1999), S. 186-193 
    Details
    ISSN: 1432-2234
    Keywords: Key words: Solvent accessibility ; Logistic function ; Hydrophobicity ; Burial index ; Amino acids
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract. For predicting solvent accessibility from the sequence of amino acids in proteins, we use a logistic function trained on a non-redundant protein database. Using a principal component analysis, we find that the prediction can be considered, in a good approximation, as a monofactorial problem: a crossed effect of the burial propensity of amino acids and of their locations at positions flanking the amino acid of interest. Complementary effects depend on the presence of certain amino acids (mostly P, G and C) at given positions. We have refined the predictive model (1) by adding supplementary input data, (2) by using a strategy of prediction correction and (3) by adapting the decision rules according to the amino acid type. We obtain a best score of 77.6% correct prediction for a relative accessibility of 9%. However, compared to trivial strategy only based upon the frequencies of buried or exposed residues, the gain is less than 4%.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s002140050428
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  • 56
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    Effect of acute and chronic exercise on plasma amino acids and prolactin concentrations and on [3H]ketanserin binding to serotonin2A receptors on human platelets (1999)
    Springer
    European journal of applied physiology 79 (1999), S. 318-324 
    Details
    ISSN: 1439-6327
    Keywords: Key words Endurance exercise ; Amino acids ; Serotonin ; Central fatigue ; Overtraining
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract The neurotransmitter serotonin (5-hydroxytryptamine, 5-HT) has been shown to modulate various physiological and psychological functions such as fatigue. Altered regulation of the serotonergic system has been suggested to play a role in response to exercise stress. In the present study, the influence was investigated of acute endurance exercise and short-term increase in the amount of training on the concentrations of the 5-HT precursor tryptophan (TRP), of prolactin (PRL) and of branched-chain amino acids (BCAA) in the blood, as well as on the binding of [3H]ketanserin to the serotonin-2A (5-HT2A) receptors on platelets. Nine healthy endurance-trained men were tested the day before (I) and after (II) a 9-day training programme. Samples of venous blood were drawn after an overnight fast and following 5 h of cycling. Fasted and post-exercise plasma concentrations of free TRP, BCAA and free TRP:BCAA ratio did not differ between I and II. A significant decrease of plasma BCAA (P 〈 0.01) and significant augmentations of plasma free TRP, free TRP:BCAA ratio and PRL (P 〈 0.01) were found post-exercise. The increase in plasma PRL was smaller in II compared with I. Acute endurance exercise reduced the density of platelet 5-HT2A receptor [3H]ketanserin binding sites at I and II (P 〈 0.05). The basal density of the binding sites and the affinity of [3H]ketanserin for these binding sites were unaffected by an increase in the amount of training. The present results support the hypothesis that acute endurance exercise may increase 5-HT availability. This was reflected in the periphery by increased concentration of the 5-HT precursor free TRP, by increased plasma PRL concentration, and by a reduction of 5-HT2A receptors on platelets. It remains to be resolved whether these alterations in the periphery occur in parallel with an increase in the availability of 5-HT in the brain.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/s004210050514
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  • 57
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    Possible nutritional implications of varietal influence on the 7S/11S seed globulin ratios in Amaranth (1999)
    Springer
    Plant foods for human nutrition 54 (1999), S. 375-380 
    Details
    ISSN: 1573-9104
    Keywords: 7S/11S ratios ; Amaranth ; Amino acids ; Nutrition ; Varieties
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract 7S/11S seed globulin ratios were determined for sevencurrently available Amaranthus hybrid linesi.e., Amaranthus K266, K283, K343, K432, K433,K436 and MT-3. Of the seven Amaranthus linesinvestigated, four lines had 7S/11S globulin ratiosranging from 0.47 to 0.81, while three lines werefound to contain exclusively the 11S globulin form. In general, 7S globulins contained lower levels ofessential amino acids such as tryptophan, methionine,lysine, histidine, phenylalanine, valine andisoleucine than the 11S globulins.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008153925283
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  • 58
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    Electronic Resource
    Agglutinating activity of alcohol-soluble proteins from quinoa seed flour in celiac disease (1999)
    Springer
    Plant foods for human nutrition 54 (1999), S. 93-100 
    Details
    ISSN: 1573-9104
    Keywords: Amino acids ; Celiac disease ; Cells ; Cereals ; Prolamines ; Quinoa seeds
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract The edible seeds of the quinoa plant contain small quantities of alcohol-soluble protein which, after peptic-tryptic digestion, are unable to agglutinate K562(s) cells. When separated by affinity chromatography on sepharose-6B coupled with mannan, peptic-tryptic digest separated in two fractions. Fraction B peptides (about 1% of total protein) were shown to agglutinate K562(s) cells at a very low concentration, whereas peptides in fraction A and in the mixed fraction A+B were inactive, suggesting that fraction A contains protective peptides that interfere with the agglutinating activity of toxic peptides in fraction B.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008059519025
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  • 59
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    Chemical analysis and nutritional assessment of Teramnus labialis (L.) Spreng. (Fabaceae) (1999)
    Springer
    Plant foods for human nutrition 54 (1999), S. 345-352 
    Details
    ISSN: 1573-9104
    Keywords: Amino acids ; Antinutritional factors ; Protein fractionation ; Proximate composition ; Teramnus labialis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Agriculture, Forestry, Horticulture, Fishery, Domestic Science, Nutrition
    Notes: Abstract Seeds of Teramnus labialis (L.) Spreng.(Fabaceae), used as food by Malayali tribals in theKollihills of Salem District, Tamil Nadu in SouthIndia, were investigated for their nutritional value. These seeds were analyzed for proximate composition,total (true) seed proteins, seed proteinfractions, amino acid composition, fatty acidcomposition, minerals and antinutritional factors. Crude protein, crude fat, ash, and nitrogen freeextracts constituted 22.86%, 6.10%, 4.62%, and,58.15%, respectively, of the seed weight. The caloricvalue of 100 g dry matter of seed material was 378.94kcal. The essential amino acids lysine, leucine +isoleucine, arginine, valine and histidine werepresent in relatively large quantities. Theunsaturated fatty acids constituted more than 60% ofthe crude fat. Concentrations of minerals such aspotassium, magnesium, calcium, and, phosphorus werehigh. Antinutritional factors such as total freephenols, tannins, L-DOPA, hydrogen cyanide andphytic acid were present in minute quantities. Theseantinutritional factors are potentially eliminated using the conventional method of soaking the seeds in water,boiling with water and decanting prior to consumption.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008101805505
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  • 60
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    Disturbances of Amino Acids from Temporal Lobe Synaptosomes in Human Complex Partial Epilepsy (1999)
    Springer
    Neurochemical research 24 (1999), S. 1379-1383 
    Details
    ISSN: 1573-6903
    Keywords: Amino acids ; synaptosomes ; epilepsy ; glutamate ; GABA ; glutamine ; taurine
    Source: Springer Online Journal Archives 1860-2000
    Topics: Medicine
    Notes: Abstract We have studied the levels of neuroactive amino acids in synaptosomes (P2 fraction) isolated from brain tissue of ten patients with medically intractable epilepsy who were undergoing temporal lobectomy. First, lateral temporal tissue (nonfocal) was removed followed by medial temporal tissue (focal). A synaptosomal fraction (P2) was immediately prepared from each tissue and analyzed for free amino acid concentrations. Statistically significant reductions were seen in glutamine and GABA concentrations in focal tissue compared to nonfocal tissue. The ratio of excitatory amino acids (aspartate and glutamate) to inhibitory amino acids (taurine and GABA) was significantly higher in focal tissue compared to nonfocal. The glutamine/glutamate ratio was significantly reduced. These data support the hypothesis that alterations in the balance between excitatory and inhibitory amino acids may be involved in the expression of epilepsy.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1022528522373
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  • 61
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    Enhanced production of xylanase from Staphylococcus sp. SG-13 using amino acids (1999)
    Springer
    World journal of microbiology and biotechnology 15 (1999), S. 511-512 
    Details
    ISSN: 1573-0972
    Keywords: Amino acids ; Staphylococcus ; xylanase
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Process Engineering, Biotechnology, Nutrition Technology
    Notes: Abstract Amino acids such as DL-2-amino-n-butyric acid, DL-alanine, L-lysine monohydrochloride, DL-valine and L-proline enhanced total xylanase production from Staphylococcus sp. SG-13 up to 5.5-fold. The present study showed that xylanase production has mainly been governed by the chemical structure of amino acids and their analogues.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1023/A:1008932119389
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  • 62
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    FMOC-Cl as derivatizing agent for the analysis of amino acids and dipeptides by the absolute analysis method (1999)
    Springer
    Chromatographia 49 (1999), S. 317-320 
    Details
    ISSN: 1612-1112
    Keywords: Column liquid chromatography ; Amino acids ; FMOC derivatives ; Oligopeptides
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Summary One classical method for quantitation of amino acids in proteins is hydrolysis of the proteins and determination of the free amino acids. Although the drastic experimental conditions necessary for complete hydrolysis always cause degradation of some of the amino acids, if mild hydrolysis conditions are used, a mixture of amino acids and oligopeptides is obtained. If these conditions are adequately tuned, the oligopeptides are almost exclusively dipeptides. For this reason we have initiated a study to find a derivatizing agent suitable for the analysis of amino acids and dipeptides by an absolute method of quantitation already tested for amino acids. FMOC-Cl was found to be a suitable derivatizing agent for this purpose.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF02467563
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  • 63
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    Photochemistry of 9,10-Dicarbonyl-9,10-dihydroanthracene - A Source of 9,10-Dehydroanthracene? (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 57-60 
    Details
    ISSN: 1434-193X
    Keywords: Benzyne ; Dehydroanthracene ; Matrix isolation ; Photochemistry ; Bergman reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -9,10-Didehydroanthracene (1) is an interesting derivative of p-benzyne that has been subject of several studies. In contrast to an earlier report, the photochemical decarbonylation of 9,10-dicarbonyl-9,10-dihydroanthracene (2) does not lead to 1 but rather to the ring-opened ene-diyne 4. The key intermediate for this reaction is keto carbene 7 which is formed by monodecarbonylation of 2. Carbene 7 is labile towards visible-light irradiation and easily looses the second CO molecule to give 4. Carbene 7 and diyne 4 are characterized by IR and UV/Vis spectra, the IR spectra are compared to calculations at the B3LYP/6-31G(d,p) level of theory.
    Additional Material: 2 Ill.
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  • 64
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    Reversal Diastereofacial Selectivity in the n-Butyllithium Addition to O-Protected N-Trimethylsilylimines of (2S)-Lactal: Enthalpic versus Entropic Contributions (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 61-65 
    Details
    ISSN: 1434-193X
    Keywords: Nucleophilic addition ; Solvent effect ; Reversal of diastereoselectivity ; Temperature effect ; Imines ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Commonly observed, but rarely explored, is the possibility of modifying the diastereomeric excess (de%) by means of temperature. A complete reversal in the diastereofacial selectivity could be obtained whenever the diastereoisomers concerned are differentially favored by enthalpy and entropy. The enthalpic or entropic dominance of a diastereoisomer depends greatly on the reaction solvent used.
    Additional Material: 1 Ill.
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  • 65
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    Syntheses of Donor-Acceptor-Substituted 2,6-Stellanes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 73-81 
    Details
    ISSN: 1434-193X
    Keywords: Donor-acceptor systems ; Cage compounds ; Stelladione ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A number of condensations could be carried out using tricyclo[3.3.0.03,7]octane-2-one (stellanone, 4) and tricyclo[3.3.0.03,7]octane-2,6-dione (2,6-stelladione, 5) as starting materials. The components for condensations were 2-trimethylsilyl-1,3-dithiane (6), 1,1-bis(trimethylsilyl)-1H-cyclopropa[b]naphthalene (7), its 3,6-dimethoxy-substituted analogue 8, fluorene (12), xanthene (13), diethyl malonate (14), and malononitrile (15). The condensation reactions with 5 yielded mono- and disubstituted products, among them were the donor-acceptor-substituted 2,6-stellanes 33-35. The structures of 18 (prepared from stellanone and fluorene), 19, 24, 27, 31 and 32 (synthesized by condensation of 2,6-stelladione and 2-trimethylsilyl-1,3-dithiane and malononitrile, respectively) were determined by X-ray crystallography.
    Additional Material: 1 Ill.
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  • 66
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    Synthesis of ω-Nitro Acids and ω-Amino Acids by Ring Cleavage of α-Nitrocycloalkanones (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 87-90 
    Details
    ISSN: 1434-193X
    Keywords: Water ; α-Nitrocycloalkanones ; ω-Nitro acids ; Surfactant ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reaction of various α-nitrocycloalkanones 1 with aqueous 0.05 M NaOH, at 80 °C, in the presence of cetyltrimethylammonium chloride (CTACl) as a cationic surfactant, produces ω-nitro acids 2 in good yields. Reduction of the latter with HCOONH4/Pd-C, in methanol, at 80 °C affords ω-amino acids 3. The synthesis of methyl 9-oxodecanoate (8) is also reported.
    Additional Material: 2 Tab.
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  • 67
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    On the Selective O-Alkylation of Ambident Nucleophiles - The Synthesis of Thiohydroxamic Acid O-Esters by Phase-Transfer Reactions (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 97-106 
    Details
    ISSN: 1434-193X
    Keywords: O-Alkylation ; Ambident nucleophile ; Thiazolethione ; Thiohydroxamic acid ; Phase-transfer reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -O-Alkylation of cyclic thiohydroxamic acids 1 and 3-5 has been studied with a view to developing an efficient method for the synthesis of N-(alkoxy)pyridine-2(1H)-thiones and N-(alkoxy)thiazole-2(3H)-thiones. Four issues have been addressed and the following conclusions can be drawn: (i) Thiones 1 and 5 exist as O-H acids in the solid state. (ii) According to NMR investigations (1H, 13C), the thione structures should be largely retained in CDCl3, [D6]DMSO, and CD3OD solutions of acids 1, 3-5, as is also the case for pyridinethione salts 2a-h. (iii) O-Alkylation of pyridinethione salts occurs in competition with S-alkylation. Selective O-alkylation is however possible, if thiohydroxamate salts with large countercations, such as M = NBu4, are treated with hard alkylating reagents in polar aprotic media. (iv) As tetrabutylammonium thiohydroxamates, such as 2f, are highly useful in the synthesis of cyclic thiohydroxamic acid O-esters, we have developed an efficient protocol for the preparation of N-(alkoxy)pyridine-2(1H)-thiones directly from acid 1 using phase-transfer conditions (alkyl halide or sulfonic acid ester, CH3CN, K2CO3, Bu4NHSO4). This method has proved particularly successful for the synthesis of N-(alkoxy)thiazole-2(3H)-thiones 11, 20-28, which were obtained in yields of up to 87%.
    Additional Material: 2 Ill.
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  • 68
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    Palladium(0)-Catalyzed Asymmetric Synthesis of 1,2,3,4-Tetrahydro-2-vinylquinoxalines (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 129-134 
    Details
    ISSN: 1434-193X
    Keywords: Tetrahydro-2-vinylquinoxaline ; Cyclization ; Palladium ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Reaction of (Z)-1,2-bis(methoxycarbonyloxy)but-2-ene (2) with various N,N-bis(arylsulfonyl)-o-phenylenediamines 1 was catalyzed by a palladium complex associated with chiral ligands to give optically active 1,4-bis(arylsulfonyl)-1,2,3,4-tetrahydro-2-vinylquinoxalines 3 with up to 62% ee. The use of (S)-MeOBIPHEP as the chiral ligand and N,N-bis(p-tolylsulfonyl)-o-phenylenediamine (1i) as the nucleophile led to the highest ee at 25 °C, regardless of the solvent used. The enantioselectivity of the cyclization is strongly affected by the nature of the substituents at the nitrogen atom.
    Additional Material: 4 Tab.
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  • 69
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    Stereoselective Synthesis of Enantiomerically Pure β-Fluoroalkyl γ-Butyrolactones by Sulfoxide-Directed Lactonization (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 111-115 
    Details
    ISSN: 1434-193X
    Keywords: Fluorine ; Lactones ; Annulation ; Ketene ; Sulfoxides ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiomerically pure α,α-dichloro β-fluoroalkyl γ-p-tolylthio γ-butyrolactones trans-6a-c have been obtained with excellent stereocontrol (〉 98:2) and enantiomeric purity (〉 98:2) by sulfoxide-directed lactonization (Marino's annu-lation reaction) of β-fluoroalkyl vinyl sulfoxides (R)-(E)-5a-c with dichloroketene. Highly chemoselective dechlorination and desulfurization reactions performed on trans-6c efficiently provided the β-chlorodifluoromethyl γ-butyrolactone (S)-8c, the absolute stereochemistry of which was determined by X-ray diffraction analysis of its γ-p-tolylthio precursor (2R,3S)-7c.
    Additional Material: 1 Ill.
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  • 70
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    Reaction of Nitrosobenzene with 4-Methoxy-N-methyleneaniline (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 141-143 
    Details
    ISSN: 1434-193X
    Keywords: Nitrosobenzene ; 4-Methoxy-N-methyleneaniline ; 1,3,5-Tris(4-methoxyphenyl)-1,3,5-triazinane ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A 1:1 adduct produced in the reaction of nitrosobenzene (2) with 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane (3) has been shown by X-ray diffraction structure analysis to be the N′-(4-methoxyphenyl)-N-phenyl-N-oxyformamidinium species 5.
    Additional Material: 1 Ill.
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    A New Diastereoselective Synthesis of anti-α-Alkyl α-Hydroxy β-Amino Acids (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 155-161 
    Details
    ISSN: 1434-193X
    Keywords: Alkylation ; Oxazolines ; anti-α-Alkyl α-hydroxy β-amino acids ; Lithium dianion ; Penicillin G acylase ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -As part of an ongoing project concerning the synthesis of enantiomerically pure α-hydroxy β-amino acids, we have now developed a general strategy allowing the synthesis of anti-α-alkyl α-hydroxy β-amino acids. Our procedure involves the intermediate formation of trans-oxazolines, which are alkylated at C-5 with good to high diastereoselectivity and then hydrolysed under mildly acidic conditions, affording in quantitative yield the corresponding hydroxy amides. The starting (R)-3-amino-3-phenylpropanoic acid and (S)-3-aminobutanoic acid were obtained in enantiomerically pure form by selective enzymatic hydrolysis of the corresponding phenylacetylamides with penicillin G acylase.
    Additional Material: 3 Ill.
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  • 72
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    Palladium(0)-Catalyzed Reaction of Acidic Anilines with (Z)-2-Butene-1,4-diyl Dicarbonate - Preparation of N-Aryl-4-vinyloxazolidin-2-ones (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 181-186 
    Details
    ISSN: 1434-193X
    Keywords: Palladium catalysis ; Homogeneous catalysis ; Anilines ; Alkylation ; Oxazolidinones ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Palladium-catalyzed reaction of acidic anilines with (Z)-2-butene-1,4-diyl dicarbonate affords N-aryl-4-vinyloxazolidin-2-ones. The success of the reaction depends on the acidity of the aniline and requires in situ conversion of the dicarbonate into carbamate carbonate by nucleophilic attack of the aniline conjugate base followed by palladium-catalyzed intramolecular cyclization.
    Additional Material: 1 Tab.
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  • 73
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    Substituent Effects on the Vinylcyclopropane-Cyclopentene Rearrangement - A Theoretical Study by Restricted and Unrestricted Density Functional Theory (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 215-220 
    Details
    ISSN: 1434-193X
    Keywords: Density functional calculations ; Vinylcyclopropane-cyclopentene rearrangement ; [1,3]-Sigmatropic shift ; Biradical-like transition structure ; Substituent effects ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The effect of donor substitution by the hydroxy group and of acceptor substitution by the cyano group on the activation energies of the vinylcyclopropane-cyclopentene rearrangement was calculated by the spin-restricted RB3LYP/6-31G* method for reactant structures and by the spin-unrestricted UB3LYP/6-31G* method for transition structures. The activation energies of the rearrangement of hydroxy- and cyano-substituted vinylcyclopropanes are very similar for substitution in the same position. In agreement with earlier findings the substituent effects on the activation energies are closely connected with the radical stabilizing properties of the substituents. As indicated by singlet/triplet splitting energies, the transition structures are essentially biradicaloid. In spite of spin pairing in the transition structure the substituent effects on bond lengths and on stabilization energies are very similar to those of the free radicals corresponding to the two radical substructures. Thus, the transition structures may be considered, in good approximation, as structures consisting of two weakly interacting radicals.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98349_s.pdf or from the author.
    Additional Material: 5 Ill.
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  • 74
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    Syntheses and Reactions of 1-Amino-2,2-dialkylcyclopropane-1-carbonitriles and -carboxamides - Potential Precursors of ACC Derivatives (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 239-250 
    Details
    ISSN: 1434-193X
    Keywords: Cyclopropanes ; Rearrangements ; Cyanohydrins ; Schiff bases ; Small ring systems ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The direct cyclization of 2-amino-4-chloro-3,3-dimethylbutanenitrile with potassium tert-butoxide in THF afforded 1-amino-2,2-dimethylcyclopropane-1-carbonitrile and a dimerization product. Various new cis- and trans-1-(tert-butylamino)-2-benzyl-2-methylcyclopropane-carbonitriles and© the corresponding cyclopropanecarboxamides have been synthesized, with focus on the isolation of the pure stereoisomeric cyclopropanecarboxamides. The relative configuration of the stereoisomers was established by X-ray crystallographic analysis of one of the model compounds. A new route to the latter functionalized cyclopropanes was developed by reaction of 1-methoxycyclopropylamines with potassium cyanide. Some remarkable rearrangements of 1-aminocyclopropane-1-carbonitriles into azetidine and oxazine derivatives via Favorskii-derived intermediates are reported. Various aspects of the chemistry of geminally functionalized cyclopropanes are discussed.
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    Regio- and Stereoselective Synthesis of Vinylallenes by 1,5-(SN′′)-Substitution of Enyne Acetates and Oxiranes with Organocuprates (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 267-275 
    Details
    ISSN: 1434-193X
    Keywords: Vinylallenes ; Organocuprates ; Substitution ; Stereoselective synthesis ; Copper catalysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enyne acetates 2, 4, 6, and 8, as well as enyne oxiranes 10, with different substitution patterns react with organocuprates regioselectively under 1,5-(SN2′′)-substitution to provide vinylallenes 11 and 12. With lithium dimethylcuprate, reduced vinylallenes originating from a (formal) transfer of a hydride ion to the substrate are formed in some cases. The products are usually obtained as mixtures of (E/Z)isomers; however, pure (E)-vinylallenes are formed occasionally. The 1,5-substitutions can also be carried out with catalytic amounts of copper reagents. The reaction of chiral enyne acetate (S)-2a with tBu2CuLi · LiCN proceeds enantioselectively, so that this transformation constitutes a new case of remote stereocontrol.
    Additional Material: 1 Tab.
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    Reactions of the Hydrofluoroborate Salts of Open-Chain Analogues of Reissert Compounds with Some α,β-Ethylenic Esters (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 297-303 
    Details
    ISSN: 1434-193X
    Keywords: Nitrogen heterocycles ; Open-chain analogue of Reissert compound ; Hydrofluoroborate salts ; α,β-Ethylenic esters ; 1,3-Dipolar cycloaddition ; Azomethine ylide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a münchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement-condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
    Additional Material: 5 Ill.
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    EPC-Synthesis of β-Amino Acid Derivatives through Lithiated Hydropyrimidines (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 335-360 
    Details
    ISSN: 1434-193X
    Keywords: 2-tert-Butylhydropyrimidinones ; 3-Aminocarboxylic acid derivatives ; Cyclic imino esters ; Lithium enaminates ; Alkylations ; β-Amino acids ; Asymmetric synthesis ; Kinetic resolution ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Racemic and enantiopure 2-tert-butyltetrahydropyrimidinones (from pivalaldehyde and 3-aminocarboxylic acids) are converted to Alloc-, Boc-, and Z-protected cyclic imino esters (7-10, Schemes 2-4). These are deprotonated to Li enaminates (K, L). Reactions with electrophiles (prim., sec. alkyl, allyl, benzyl, propargyl halides, aldehydes, imines, enoates) give good yields and are highly diastereoselective (products 11-42, Schemes 5-10). A two-step cleavage (removal of protecting group and hydrolysis) under very mild conditions converts the heterocyclic products to α-branched β-amino acid methyl esters (43-61, Schemes 11-13). The structure of the products is determined by NMR spectroscopy (Figure 1), by chemical correlation (Scheme 14), and by X-ray analysis (Figure 2, 3, 7, Table 1). A structure of the Li enaminates is proposed (Figure 4). Mechanistic models are derived for the reactions occurring with formation of two stereogenic centers with relative topicity like (Figures 5, 6).
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    A Unified Synthetic Strategy for the Indolopyridine Alkaloid Group (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 373-378 
    Details
    ISSN: 1434-193X
    Keywords: Alkaloids ; Cross-coupling ; N-Heterocycles ; Palladium ; Synthesis design ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Thermal or acetyl chloride induced cyclization of bromoenamide 10 affords the pentacyclic derivative 12 with high yield and regioselectivity. From this common synthetic intermediate, palladium-catalyzed reactions allow the total synthesis of indolopyridine alkaloids 1-6.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98332_s.pdf or from the author.
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  • 79
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    Conformational Preferences of Peptides Containing Reverse-Turn Mimetic Bicyclic Lactams: Inverse γ-Turns versus Type-II′ β-Turns - Insights into β-Hairpin Stability (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 389-400 
    Details
    ISSN: 1434-193X
    Keywords: Reverse-turn mimics ; γ-Turns ; β-Turns ; β-Hairpins ; NMR spectroscopy ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The solid-phase synthesis and characterization of a series of peptides (3-9), containing reverse-turn mimetic bicyclic lactams (1a, 1b), was reported in the preceding paper. The bicyclic lactams (1a, 1b) possess high structural similarity to the two central residues of a β-turn. The conformational preferences of the constrained peptides have been investigated by NMR spectroscopy and IR spectroscopy. Our experimental results have been complemented by computer modelling studies and show that the constrained peptides (3-9) form an inverse γ-turn or a type-II′ β-turn through intramolecular hydrogen bonding, depending on the nature of the reverse-turn mimic. In N-acetylated tetrapeptide mimics incorporating the two different bicyclic lactams (a series and b series), H5 is available for either a γ-turn (7-membered ring with the carbonyl group of the bicyclic lactam) or a β-turn (10-membered ring with the carbonyl group of residue 2), as shown in Figures 7 and 9. The a series incorporating the (5,7)-bicyclic lactam predominantly induces the γ-turn conformation, while the b series incorporating the (5,6)-bicyclic lactam can promote either a γ-turn or a β-turn conformation, with the β-turn usually being preferred and with varying degrees of β-hairpin formation.
    Additional Material: 10 Ill.
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    Deprotonation of Oxazolinyloxiranes: Formation of Substituted Acyloxiranes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 409-417 
    Details
    ISSN: 1434-193X
    Keywords: Deprotonation ; Oxiranyloxazolines ; Oxazolinyloxiranyllithium compounds ; Oxazolidines ; Acyloxiranes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at -100 °C in Et2O furnishes oxazolinyloxiranyllithium compounds[1]1b, 1i, and 1l which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c-1g and 1j. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-(4,4-dimethyl-2-oxazolinyl)-2-p-tolylepoxyethane (1h) was found to be configurationally stable while oxiranyllithium 1l, generated from the cis isomer 1k, was not. Oxazolinylepoxides 1d, 1j, and 1m could be deblocked to acyloxiranes 5a-e through oxazolidines 4a-e.
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    N-Substituted 1-Aminoindoles from Electrogenerated N-Substituted 2-(ortho-Nitrosophenyl)ethylamines (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 419-430 
    Details
    ISSN: 1434-193X
    Keywords: Electrochemistry ; Electrosynthesis ; Nitrosobenzenes ; Nitrogen heterocycles ; 1-Aminoindoles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -An electrochemical methodology offering efficient access to N-alkyl- and N-aryl-substituted 1-aminoindoles has been developed. N-Substituted 2-(ortho-nitrosophenyl)ethylamines, electrogenerated in a “redox” flow cell, undergo intramolecular cyclization to hydrocinnoline-type intermediates. Under slightly basic conditions, these undergo spontaneous ring-contraction to produce the N-substituted heterocycles in good yields. The reactions have been studied in slightly acidic and slightly basic aqueous alcoholic media.
    Additional Material: 11 Ill.
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  • 82
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    Synthesis of Enantiopure β- and γ-Amino Alcohols from Homochiral α- and β-Aminoacylsilanes as Stable Synthetic Equivalents of α- and β-Amino Aldehydes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 437-445 
    Details
    ISSN: 1434-193X
    Keywords: Aminoacylsilanes ; Amino aldehydes ; Amino alcohols ; Allylation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A practical route is described for the synthesis of enantiopure β- and γ-amino alcohols with two stereocenters, starting from homochiral α- (1 and 5) and β- (13 and 16) -aminoacylsilanes, and involving stereoselective addition of allylmetal compounds and subsequent stereospecific protiodesilylation of the adducts. The degree of diastereoselectivity achieved in the nucleophilic addition step depends on both the nitrogen-protecting group and the reagents used. Diastereomeric excess (de) values equal to or higher than 98% were obtained in the TiCl4-promoted allylation of the N-Pht-aminoacylsilanes 1 and 13 and of the N-Ts-aminoacylsilane 5 with allyltrimethylsilane. Lower de values were obtained in the Sc(OTf)3-catalyzed allylation of 5 with tetraallyltin and in the additions of both allyltrimethylsilane and tetraallyltin to the N-Ts-β-aminoacylsilane 16. Protiodesilylation of the adducts, leading to the β- and γ-amino alcohols, was accomplished with TBAF, except in the case of the adducts obtained from 5. For these, a preliminary removal of the tosyl group was necessary, which was accomplished with simultaneous desilylation by treatment with Na in liquid ammonia.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98342_s.pdf or from the author.
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  • 83
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    Diastereoselective Intramolecular meta Photocycloaddition of Side-Chain-Substituted 5-(2-Methoxyphenyl)pent-1-enes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 463-470 
    Details
    ISSN: 1434-193X
    Keywords: meta Photocycloaddition ; Photochemistry ; Steric hindrance ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Irradiation of a series of 5-(2-methoxyphenyl)pent-1-enes substituted with a hydroxy or trimethylsilyloxy group at the α-, β-, or γ-position of the side-chain yields in all cases meta photocycloadducts, in which the configuration at the substituted carbon atom is mainly endo. This indicates that the diastereoselectivity originates from minimization of steric interactions between the side-chain substituent and the ortho-methoxy group at the arene unit. Hydrogen bonding does not seem to be involved. The introduction of the side-chain substituents also influences the regioselectivity of the addition: The linear to angular adduct ratios are significantly increased compared to the case of the parent compound.
    Additional Material: 3 Tab.
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  • 84
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    5-Aza-7-deaza-2′-deoxyguanosine: Oligonucleotide Duplexes with Novel Base Pairs, Parallel Chain Orientation and Protonation Sites in the Core of a Double Helix (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 485-496 
    Details
    ISSN: 1434-193X
    Keywords: 5-Aza-7-deaza-2′-deoxyguanosine ; Oligonucleotides ; Parallel DNA ; Protonated base pairs ; Tm values ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Oligonucleotides containing 5-aza-7-deaza-2′-deoxyguanosine (1) were synthesized. Solid-phase synthesis was performed with the phosphonate 15 or the phosphoramidite 5. The amino-unprotected phosphonate 4 was also employed. Hybridization studies of oligonucleotides containing 1 resulted in new base pairs leading to duplexes with parallel (ps) or antiparallel (aps) chain orientation. Among those with parallel chains a stable “purine-purine” base pair was observed between 5-aza-7-deazaguanine and guanine or 7-deazaguanine. Antiparallel stranded duplexes are formed when 5-aza-7-deazaguanine pairs with cytosine. This base pair has only two hydrogen bonds under neutral conditions but is stabilized by a third one in acidic medium. A new base pair is also detected between the base of 1 and isoguanine (neutral medium).
    Additional Material: 1 Ill.
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    Polar and Steric Substituent Effects in 5-exo-trig Cyclizations of 1-Aryl-4-penten-1-oxyl Radicals (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 523-523 
    Details
    ISSN: 1434-193X
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -By mistake wrong concentrations were given in the footnote of Table 1 and in the Discussion. Instead of c0 = 1.2 M read c0 = 0.12 M if 2-naphthalenethiol was used as hydrogen donor and instead of c0 = 1.8 M read c0 = 0.18 M if Bu3SnH was used to trap photoproducts. In Table 2 relative rate constants of radical 2d refer to radical 2e and vice versa as correctly stated in the Discussion. In the Experimental Section (Iodocyclization) read 2.25 g (8.86 mmol) of iodine instead of 2.25 g (1.10 mmol) of iodine.
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  • 86
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    Arylboron Compounds as Acid Catalysts in Organic Synthetic Transformations (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 527-538 
    Details
    ISSN: 1434-193X
    Keywords: Tris(pentafluorophenyl)borane ; Diarylborinic acid ; Arylboronic acid ; Chiral arylboron catalyst ; Lewis acid ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Arylboron compounds, ArnB(OH)3-n (n = 1-3), bearing electron-withdrawing aromatic groups such as triarylboranes, diarylborinic acids, and arylboronic acids represent a new class of air-stable and water-tolerant Lewis acid or Brønsted acid catalysts in organic synthesis. In particular, while tris(pentafluorophenyl)borane has primarily been used as a co-catalyst in metallocene-mediated olefin polymerization, its potential as a Lewis acid catalyst for organic transformation is now much more extensive. Diarylborinic acids and arylboronic acids have shown themselves to be powerful tools in the design of chiral boron catalysts. This article provides a comprehensive summary of the organic transformations catalyzed by arylboron compounds as acids.
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    2D-NMR-Guided Constitutional Analysis of Organic Compounds Employing the Computer Program COCON[#] (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 573-577 
    Details
    ISSN: 1434-193X
    Keywords: Structure elucidation ; Constitutional analysis ; Natural products ; HMBC ; Computational chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The computer program COCON is introduced as a tool for the comprehensive structure elucidation of unknown organic compounds. In particular, structural proposals made on the basis of the molecular formula and of 2D-NMR experiments can be analyzed for the existence of alternative constitutions being in agreement with the same data set. The computational speed grounds on the evaluation of ambiguous long-range connectivity information during the process of structure generation. The data set experimentally obtained for the marine natural product oroidin (1) was selected, because proton-poor compounds usually cause uncertainties in NMR-based structure determinations. The calculation results encourage to move from the experience-based analysis of NMR chemical shifts or of MS fragmentations to the automated evaluation of routinely available connectivity information.Supporting information for this article is available on the WWW under -http://www.wileY-Vch.de/contents/jc_2046/1999/98241_s.pdf or from the author.
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  • 88
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    3,5-Dimesityl-1,2,4-oxadiphosphole - Synthesis and Reactivity of a Novel Heterocycle (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 587-595 
    Details
    ISSN: 1434-193X
    Keywords: Phosphaalkenes ; Heterodiphospholes ; Cycloadditions ; Phosphaalkyne cyclooligomers ; Phosphorus-carbon cage compounds ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The first synthesis of a 1,2,4-oxadiphosphole 6 has been achieved by vacuum thermolysis of mesitylphosphaalkene 5. The novel heterocycle 6 exhibits an enormous potential for cycloaddition reactions, which predominantly proceed selectively at low temperatures. Compound 6 undergoes addition with two equivalents of phosphaalkynes 10 by a [4+2] cycloaddition/homo Diels-Alder reaction sequence to form novel oxatetraphosphadeltacyclenes 12 and 13. Tetrachloro-o-benzoquinone (14) undergoes a selective [4+1] cycloaddition with 12 and 13 leading to the spirocyclic products 15 and 16 containing λ5-phosphorus atoms. Treatment of the oxadiphosphole 6 with dimethyl acetylenedicarboxylate (17) provides the first access to a 1,2-oxaphosphole 18, which is formed after an initial [4+2] cycloaddition followed by a retro Diels-Alder reaction. An unexpected reaction of 6 is observed with tri-tert-butylazete (20) furnishing a new polycyclic system (→ 21).
    Additional Material: 4 Ill.
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    Synthesis of 1β-Methylcarbapenem Antibiotic Precursors by Cyclization Using π-Allylpalladium Complexes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 621-626 
    Details
    ISSN: 1434-193X
    Keywords: 1β-Methylcarbapenems ; Palladium ; Ruthenium ; Catalysis ; Cyclizations ; Stereoselective hydrogenation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -An efficient diastereoselective multi-step synthesis of bicyclic 1β-methylcarbapenem antibiotic precursors has been developed, starting from the commercially available 4-acetoxyazetidin-2-one 4. Chiral ruthenium catalysts are used in the hydrogenation step to control the β-stereochemistry at the 1-position, and a π-allylpalladium ring-closure strategy is used to form the functionalized carbapenem skeleton.
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    Oligo-2,6-naphthylenevinylenes - New Building Blocks for the Preparation of Photoluminescent Polymeric Materials (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 643-651 
    Details
    ISSN: 1434-193X
    Keywords: Oligomers ; Synthesis design ; Substituent effects ; Luminescence ; Cyclic voltammetry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Synthetic strategies towards appropriate symmetric and unsymmetric functionalization of the naphthalene ring are presented. By means of Knoevenagel and Wittig condensation reactions new fluorescent, differently functionalized oligo(2,6-naphthylenevinylene)s have been synthesized, the presence of terminal aldehyde or bromine substitution opening the way to the incorporation of the fluorescent trimers in a variety of polymeric materials. The effect of substituting the phenylene ring by the more bulky dialkoxynaphthalene system in arylenevinylene-type materials is studied from the structural point of view and the possibility to tune the emission color and the electron affinity through the introduction of naphthylenevinylene and cyano-substituted naphthylenevinylene units is also investigated.
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    New Type of Skipped Oligoaziridines: Synthesis of New Fatty AcidDerivatives Containing Aziridine Functions (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 661-664 
    Details
    ISSN: 1434-193X
    Keywords: Aziridines ; N-Heterocycles ; Fatty acids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The first successful preparation of the aziridines methyl cis-9,10;cis-12,13-diepiminooctadecanoate (3) derived from linoleic acid, and methyl cis-9,10;cis-12,13;cis-15,16-triepiminooctadecanoate (6) derived from linolenic acid, is reported. Remarkably, the bis- and trisaziridine were obtained in a reaction sequence that consists of only two steps, using technically pure methyl esters of epoxidized sunflower and linseed oil. The conversion of methyl 9,10;12,13-diepoxyoctadecanoate (1), with sodium azide and ammonium chloride in ethanol in the presence of water, yielded the new diazidodihydroxy compound methyl 9(10),12(13)-diazido-10(9),13(12)-dihydroxyoctadecanoate (2) in the first step. 2 was obtained as a regioisomeric mixture. The reaction of 2 with triphenylphosphane led to the bisaziridine 3. The analogous conversion of methyl 9,10;12,13;15,16-triepoxyoctadecanoate (4), via the new triazidotrihydroxy compound methyl 9(10),12(13),15(16)-triazido-10(9),13(12),16(15)-trihydroxyoctadecanoate (5), afforded trisaziridine 6.
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  • 92
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    Novel Ligands for the Separation of Trivalent Lanthanides and Actinides - Tetrakis(phosphane sulfide) and -(phosphinic acid) Cavitands (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 665-674 
    Details
    ISSN: 1434-193X
    Keywords: Cavitands ; Nuclear waste ; Actinide/lanthanide separation ; Solvent extraction ; Sulfur atoms ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Cavitands with phosphane sulfide moieties 4 and 8a,b were prepared in good yields from their phosphane oxide analogues, as more stable alternatives for the dithiophosphinic acids used at present. The cavitands 7a and 7b with flexible butoxyphosphane oxide ligating sites are more efficient than cavitand 3 having rigid methylphosphane oxide groups as was studied with EuIII picrate extractions. Due to the absence of an ionic functionality in the phosphane sulfides 4 and 8a,b AmIII and EuIII are not extracted, not even in the presence of synergents (e.g. TBP, TOPO, HDNNS). Cavitand 10 with phosphinic acid groups efficiently extracts EuIII in 1:1 or 2:1 complexes, depending on the metal-to-ligand concentration ratio (extraction constants Kex1 = 3.9·10-5M2 and Kex2 = 1.9·102M, respectively). Furthermore, in the case of 10 EuIII is preferentially extracted over AmIII with a separation factor SEu/Am up to 5.
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    Preparation of 2,3,5-Tri-O-benzyl-4-thio-L-arabino-furanosides and the Corresponding 4′-Thionucleoside Analogues (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 691-696 
    Details
    ISSN: 1434-193X
    Keywords: Carbohydrates ; 4-Thiofuranosides ; Nucleosides ; Reaction mechanisms ; NOE measurements ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-arabino-furanose (9) has been prepared from D-xylose via the 1,4-dithio-L-arabino-furanoside 8. The crucial step of the reaction, i.e. the intramolecular cyclization of the open-chain dithioacetal 5, has been achieved in a yield of 90% by applying tetrabutylammonium iodide as promoter. Reaction of 9 with bis(trimethylsilyl)uracil or -thymine led to the benzyl derivatives 12 and 13 from which the deprotected 4′-thionucleoside analogues 14 and 15 have been prepared by debenzylation with boron tribromide.
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    100 Years of Baeyer-Villiger Oxidations (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 737-750 
    Details
    ISSN: 1434-193X
    Keywords: Baeyer-Villiger oxidation ; Ketones ; Monopersulfate ; Peracids ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -In the present review, we report the discovery of the formation of esters and lactones by oxidation of ketones with a peroxide derivative, namely the Baeyer-Villiger reaction. This reaction was first reported by Adolf von Baeyer and Victor Villiger a century ago in 1899, just one year after the oxidant they used (KHSO5) has been described. Furthermore, Baeyer and Villiger established the composition of this new inorganic peroxide and showed that its instability was the reason of a controversy between several European chemists between 1878 and 1893. For the first 50 years the mechanism of the Baeyer-Villiger reaction was a matter of debate. A side product, 1,2,4,5-tetraoxocyclohexane, was ruled out as an intermediate in the ester formation by Dilthey. Criegee postulated a nucleophilic attack of the oxidant on the carbonyl group. This mechanism was confirmed by von E. Doering by a labeling experiment with [18O]benzophenone. The rearrangement step occurs with retention of the stereochemistry at the migrating center. The competitive migration and the rate-determining step are also discussed in this review.
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    Transferase Activity of a β-Glycosidase from Thermus thermophilus: Specificities and Limits - Application to the Synthesis of β-[1→3]-Disaccharides (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 757-763 
    Details
    ISSN: 1434-193X
    Keywords: Transglycosylation ; Glycosidases ; Thermus thermophilus ; Carbohydrates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The aim of this paper is to test the ability of a β-glycosidase from Thermus thermophilus to catalyse transglycosylation reactions in the presence of nitrophenyl glycosides as donors and other monosaccharides as acceptors. Our results show that this enzyme is able to induce such reactions either with nitrophenylgalactosides, -glucosides and -fucosides. With the two former donors, the autocondensation of the donor, which thus acts also as an acceptor, is faster than the transglycosylation with other acceptors. Furthermore, as the regioselectivity of the reactions is mainly of the β-[1→3] type, good yields are obtained for the synthesis of 2-nitrophenyl-β-D-galactopyranosyl-[1→3]-β-D-galactopyranoside and 2-nitrophenyl-β-D-glucopyranosyl-[1→3]-β-D-glucopyranoside. Conversely, in the presence of p-nitrophenylfucoside, the autocondensation is very limited, and with methyl-α-D-galactoside as an acceptor, the regioselectivity is mainly of the β-[1→6]-type resulting in the synthesis of methyl-β-D-fucopyranosyl-[1→6]-α-D-galactopyranoside.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 96
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    Electronic Resource
    Reduction of Acetylenic Compounds to (E)-Olefins by Alkali Metals - An Investigation of the Scope (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 775-779 
    Details
    ISSN: 1434-193X
    Keywords: Monoynes ; Polyynes ; Alkali metals ; Liquid NH3 ; Hexamethylphosphoric triamide ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Efficient procedures have been developed for the stereospecific reduction by alkali metals of disubstituted acetylenes with long carbon chains. Acetylenes containing two or more (isolated) triple bonds are reduced considerably more easily than are monoynes.
    Additional Material: 1 Tab.
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  • 97
    Electronic Resource
    Electronic Resource
    Synthesis of Enantiopure o-Hydroxybenzylamines by Stereoselective Reduction of 2-Imidoylphenols: Application in the Catalytic Enantioselective Addition of Diethylzinc to Aldehydes (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 805-811 
    Details
    ISSN: 1434-193X
    Keywords: Aminophenols /Asymmetric synthesis ; C-C coupling ; Reductions ; Conformation analysis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Enantiopure o-hydroxybenzylamines 2a-i were synthesized by diastereoselective reduction of the 2-imidoylphenols (R)-1a-i. Conformational analysis enabled the assignment of the absolute configurations of compounds 2a-i. The accessible o-hydroxybenzylamine (R,R)-2h serves as an effective catalyst precursor for highly enantioselective addition of diethylzinc to aliphatic and aromatic aldehydes. This pathway represents a practical and operationally very simple methodology for the enantioselective synthesis of both the enantiomers of secondary alcohols 7a-f.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
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  • 98
    Electronic Resource
    Electronic Resource
    Cyclialkylation of Arylalkyl Epoxides with Solid Acid Catalysts (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 837-846 
    Details
    ISSN: 1434-193X
    Keywords: Friedel-Crafts reaction ; Hydroxyalkylation ; Aromatics ; Epoxides ; Zeolites ; Clays ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Solid acids, such as zeolites and clays, catalyse the intramolecular hydroxyalkylation (cyclialkylation) of several arylalkyl epoxides in moderate to excellent conversions and selectivities. The use of solid acids in these cyclialkylations provides a cleaner, better alternative to conventional Lewis and Brønsted acids, enabling a more facile workup of reaction mixtures and, in several cases, better selectivities.
    Additional Material: 3 Ill.
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  • 99
    Electronic Resource
    Electronic Resource
    Phosphorylating Power of Red Phosphorus towards Aldehydes in Basic and in Acidic Media (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 861-868 
    Details
    ISSN: 1434-193X
    Keywords: Red phosphorus ; Phosphane PH3 ; Phosphorylations ; Ultrasound irradiation ; Redox chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -The reactivity of red phosphorus towards aldehydes was investigated under basic and acidic media. It was demonstrated that the real phosphorylating agent involved in the reaction was phosphane (PH3) in basic media, and hypophosphorous acid (H3PO2) in acidic media. A convenient one-pot synthesis of (α-hydroxyalkyl)phosphinic acids from red phosphorus and aldehydes in basic media was realized under sonication. The same reaction under acidic media in the presence of hydriodic acid led to the corresponding phosphonic acids. The (α-hydroxyalkyl)phosphinic acids were readily prepared under sonication from hypophosphorous acid and aldehydes in the presence of catalytic amounts of hydrochloric acid. The mechanism of the addition reaction of PH3 to benzaldehyde was elucidated and shows the complexity of the reaction as a function of the experimental conditions.
    Additional Material: 1 Tab.
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  • 100
    Electronic Resource
    Electronic Resource
    A New Approach to Erythrinanes through Pummerer-Type Cyclization (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 909-915 
    Details
    ISSN: 1434-193X
    Keywords: Erythrina alkaloids ; Nitrogen heterocycles ; Nitro aldol reaction ; Michael addition ; Pummerer reaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A successful new strategy for the synthesis of erythrinanes is reported. (Nitromethyl)arene derivative 16 was condensed with aldehyde 17 to give nitro aldol 19. After removal of the hydroxy group, the subunits 26a,b, containing the erythrinane rings A and D, were formed by intramolecular Michael addition. Reduction of the nitro function, followed by cyclization of the resulting amino group with the appended acetate group afforded the bicyclic lactams 29a,b, bearing an angular aryl group. Two-carbon elongation at the nitrogen atoms of 29a and 29b by means of hetero Michael addition of methyl phenyl sulfoxide, followed by Pummerer-type cyclization, gave cis- and trans-11-phenylthioerythrinan-8-ones 35a and 35b, respectively. Reductive desulfurization at C-11 furnished the desired erythrinan-8-ones 39a and 39b in 8 steps from 16.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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