title: 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.
abstract: 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.
authors.affiliation: Department of Chemistry and Materials Science, Tokyo Institute of Technology, Meguro, Tokyo 152-8551, Japan.
authors.forename: Youichi
authors.initials: Y
authors.lastname: Mashimo
authors.forename: Yasuyo
authors.initials: Y
authors.lastname: Sekiyama
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Araya
authors.forename: Yoshinori
authors.initials: Y
authors.lastname: Fujimoto
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D004163:Diphosphoglyceric Acids / Q000378:metabolism; D004754:Enterobacter / Q000378:metabolism*; D005990:Glycerol / Q000378:metabolism*; D006859:Hydrogen / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D019289:Pyruvic Acid / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000900:Anti-Bacterial Agents; D004163:Diphosphoglyceric Acids; C063061:agglomerin A; C015891:glycerate 1,3-biphosphate; D006859:Hydrogen; D019289:Pyruvic Acid; D015107:4-Butyrolactone; D005990:Glycerol