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Incorporation of Labeled Precursors into A16886B, a Novel -lactam Antibiotic Produced by Streptomyces Clavuligerus

Overview
Journal Antimicrob Agents Chemother
Publisher American Society for Microbiology
Specialty Pharmacology
Date 1972 Mar 1
PMID 5045471
Citations 20
Authors
J G Whitney
D R BRANNON
J A Mabe
K J Wicker
Affiliations
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Abstract

The incorporation of C-14 from amino acids into A16886B, 7-(5-amino-5-carboxyvaleramido)-7-methoxy-3-carbamoyloxymethyl-3-cephem-4- carboxylic acid, by Streptomyces clavuligerus is reported. As with cephalosporin C biosynthesis by the mold Cephalosporium acremonium, labels from cysteine, valine, and alpha-amino-adipic acid were incorporated. Unlike cephalosporin C, in A16886B label from lysine was incorporated into the alpha-aminoadipic acid side chain. Label from methionine-(14)C-methyl was incorporated into the methoxyl group. The relative percentage of incorporation of (3)H and (14)C from doubly labeled cystine suggests the improbability of the C-7 methoxyl group arising from an intermediate containing a double bond between C-6 and C-7.

Citing Articles

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Genes for beta-lactam antibiotic biosynthesis.

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A two-protein component 7 alpha-cephem-methoxylase encoded by two genes of the cephamycin C cluster converts cephalosporin C to 7-methoxycephalosporin C.

Coque J, Enguita F, Martin J, Liras P J Bacteriol. 1995; 177(8):2230-5.

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The conversion of cephalosporins to 7 alpha-methoxycephalosporins by cell-free extracts of Streptomyces clavuligerus.

OSullivan J, ABRAHAM E Biochem J. 1980; 186(2):613-6.

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Incorporation of 3H and 14C from (6 alpha-3H)penicillin N and (10-14C,6 alpha-3H) penicillin N into deacetoxycephalosporin C.

BALDWIN J, Singh P, Yoshida M, Sawada Y, DEMAIN A Biochem J. 1980; 186(3):889-95.

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References
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