Biosynthesis of agglomerin A: stereospecific incorporation of pro-R- and pro-S-hydrogens at sn-C-3 of glycerol into the branched C(3) moiety

The biosynthetic origin of the C(3) branched unit of agglomerin A has been investigated. Feeding of sn-(3R)- and sn-(3S)-[3-(2)H]glycerols to Enterobacter agglomerans PB-6042 followed by (2)H NMR analysis of the resulting agglomerin A revealed that pro-R and pro-S hydrogens at sn-C-3 of glycerol wer...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-02, Vol.14 (3), p.649-651
Main Authors: Mashimo, Youichi, Sekiyama, Yasuyo, Araya, Hiroshi, Fujimoto, Yoshinori
Format: Article
Language:English
Subjects:
4-Butyrolactone - analogs & derivatives
Anti-Bacterial Agents - biosynthesis
Diphosphoglyceric Acids - metabolism
Enterobacter - metabolism
Glycerol - metabolism
Hydrogen - metabolism
Magnetic Resonance Spectroscopy
Molecular Structure
Pyruvic Acid - metabolism
Stereoisomerism
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Summary:The biosynthetic origin of the C(3) branched unit of agglomerin A has been investigated. Feeding of sn-(3R)- and sn-(3S)-[3-(2)H]glycerols to Enterobacter agglomerans PB-6042 followed by (2)H NMR analysis of the resulting agglomerin A revealed that pro-R and pro-S hydrogens at sn-C-3 of glycerol were incorporated stereospecifically into 5E and 5Z hydrogens of agglomerin A, respectively. These results imply that the immediate precursor of the C(3) branched unit is not pyruvate, but 1,3-bisphosphoglyceric acid or its biological equivalent.
ISSN:0960-894X
1464-3405