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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Archives of microbiology 132 (1982), S. 100-102 
    ISSN: 1432-072X
    Keywords: Methyl halides ; Biosynthesis ; Stable isotopes ; Basidiomycetes ; Phellinus pomaceus
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The biosynthetic origin of themethyl group in the methyl chloride produced by cultures ofPhellinus pomaceus (Pers.) Maire has been investigated using stable isotope labeled substrates. Feeding ofd-[6,6-2H2] glucose,Dl-[3,3-2H2] serine andl-[methyl-2H3] methionine led to the production of deuterated methyl chloride in which the major labeled species contained 2, 2, and 3 deuterium atoms, respectively. The data are consistent with the methyl chloride produced by this organism being derived solely from methionine with retention of all of the methyl protons.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Springer
    Archives of microbiology 143 (1985), S. 1-5 
    ISSN: 1432-072X
    Keywords: Methanogenic bacteria ; Methanopterin ; Biosynthesis ; Stable isotopes
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology
    Notes: Abstract The biosynthesis of the 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane moiety of methanopterin was studied in methanogenic bacteria. By comparing the extent of deuteration of the benzyl group of 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane with the benzyl group of phenylalanine isolated from cells grown with [2,2,2-2H3]acetate, it was shown that the aromatic portion of the 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane was derived from an intermediate in the shikimic acid pathway which is produced prior to the formation of prephenic acid. The ready incorporation of p-aminobenzoic acid into 5-(p-aminophenyl)-1,2,3,4-tetrahydroxypentane indicates that this intermediate is chorismic acid and that p-aminobenzoic acid, a component of folic acid, is an intermediate in the formation of methanopterin.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 9 (1997), S. 678-680 
    ISSN: 0899-0042
    Keywords: methanopterin ; absolute stereochemistry ; 2-hydroxyglutaric acid ; sarcinopterin ; folates ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The absolute stereochemistry of the 2-hydroxyglutaric acid present in methanopterin and its α-glutamyl derivative, sarcinapterin, has been determined to be (S). Thus, the absolute stereochemistry of the 2-hydroxyglutaric acid present in the side chain of these modified folates is the same as the L-glutamic acid present in the side chain of folates. Chirality 9:678-680, 1997. © 1997 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
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  • 4
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 291-293 
    ISSN: 0899-0042
    Keywords: coenzymes ; 1H NMR 13C NMR ; diastereomers ; gas chromatograpy-mass spectrometry ; methanofuran ; Methanobacterium thermoautotrophicum strain ΔH ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,3,4,6-Hexanetetracarboxylic acid was first identified as a natural product during the structural characterization of methanofuran, one of several coenzymes involved in methanogenesis. A combination of high resolution 1H NMR, 13C NMR, and gas chromatography-mass spectrometry has been used to establish that the naturally occurring diastereomer of 1,3,4,6-hexanetetracarboxylic acid in methanogenic Archaea is meso. © 1996 Wiley-Liss, Inc.
    Additional Material: 1 Ill.
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  • 5
    Electronic Resource
    Electronic Resource
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 332-340 
    ISSN: 0899-0042
    Keywords: 1-[4-[[1-(2-amino-7-methyl-4-hydroxo-6-pteridinyl)ethyl]amino]phenyl]-1-deoxy-D-ribitol ; (S)-6-[1-(4-carboxymethyllanilino)ethyl]pterin ; D(+)-neopterin ; L-biopterin ; (S)-6-(1-hydroxyethyl)pterin ; (S)-6-(1-hydroxyethyl)-7-methylpterin ; (R)-6-(1-phenoxyethyl)pterin ; stereospecific synthesis ; circular dichroism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The configuration at the C-9 of methanopterin (MPT) has been determined by comparing the circular dichroism (CD) spectra of MPT and its hydrolytic fragment, 1-[4-[[1-(2-amino-7-methyl-4-hydroxy-6-pteridinyl)-ethyl]amino]phenyl]-1-deoxy-D-ribitol (HP-1), with the CD spectra of a series of model compounds of known stereochemistry. These compounds included (S)-6-[1-(4-carboxymethylanilino)ethyl]pterin, (S-6(1-hydroxyethyl)-7-methylpterin, (S-6-(1-hydroxyethyl)pterin, (R)-6-(1-phenoxyethyl)pterin, D(+)-neopterin, and L-biopterin. From this comparison it was concluded that MPT has the R configuration at C-9 and is thus configurationally related to D(+)-neopterin, which has the S configuration at C-1. From previous work establishing the relative stereochemistry at C-6, C-7, and C-9 of N5-N10-methenyl-5,6,7,8-tetrahydromethanopterin (N5-N10-methenyl-H4MPT) as R, S, and R, respectively, it is clear that the remaining asymmetric carbons at C-6 and C-7 of H4MPT have the S and S configuration, respectively. Comparison of these latter two positions to the equivalent carbons in 5,6,7,8-tetrahydrofolate (H4folate) show that the steps involved in the biological reduction of MPT to H4MPT occur with the same stereochemical outcome as those involved in the biological reduction of folate to H4folate. © 1996 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
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  • 6
    Electronic Resource
    Electronic Resource
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 10 (1983), S. 660-664 
    ISSN: 0306-042X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The incorporation of deuterated serine into cysteine during the metabolism of cystine by Escherichia coli was studied in order to determine the extent to which the carbon-sulfur bond(s) of the cystine is cleaved. The results indicate that the major route (∽80%) for cystine metabolism consists of a reductive cleavage of the cystine disulfide bond to form cysteine. Evidence is presented which shows that a portion of the remaining cystine is broken down by a pathway(s) which results in cleavage of the carbon-sulfur bond of the cystine. This pathway would be the same as that expected for the β-elimination of pyruvate from cystine catalysed by the enzyme β-cystathionase. In addition, a small portion of the resulting cysteine is shown to undergo a reversible dissociation to serine and hydrogen sulfide. Evidence is presented which shows that this dissociation is caused by the enzyme cysteine synthetase [O-acetyl-L-serine acetate-lyase (adding H2S)].
    Additional Material: 2 Tab.
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