A SUBSTRATE-ANALOG STUDY ON CLAVAMINIC ACID SYNTHASE - POSSIBLE CLUES TO THE BIOSYNTHETIC ORIGIN OF PROCLAVAMIC ACID

Incubation of (2S)-5-amino-(2'-oxoazetidin-1'-yl)pentanoic acid with clavaminic acid synthase gave (2S)-5-amino-2-(2'-oxoazetidin-1'-yl)pent-3,4-enoic acid as the major product, together with a small amount of proclavaminic acid; modification of the amino group to the guanyl grou...

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Bibliographic Details
Published inJournal of the Chemical Society. Chemical communications no. 6; pp. 500 - 502
Main Authors BALDWIN, JE, LLOYD, MD, WHASON, B, SCHOFIELD, CJ, ELSON, SW, BAGGALEY, KH, NICHOLSON, NH
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1993
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
STREPTOMYCES-CLAVULIGERUS
INTERMEDIATE
ENZYME
CLAVULANIC ACID
PRECURSORS
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Summary:Incubation of (2S)-5-amino-(2'-oxoazetidin-1'-yl)pentanoic acid with clavaminic acid synthase gave (2S)-5-amino-2-(2'-oxoazetidin-1'-yl)pent-3,4-enoic acid as the major product, together with a small amount of proclavaminic acid; modification of the amino group to the guanyl group biased the mode of reactivity from desaturation to hydroxylation.
ISSN:0022-4936
DOI:10.1039/c39930000500