Biosynthesis of Capreomycin. 2. Incorporation of l-Serine, l-Alanine, and l-2,3-Diaminopropionic Acid

Mu Wang, Steven J. Gould

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Abstract

The biosynthesis of the antitubercular antibiotic capreomycin has been studied by administration of isotopically labeled (13C and 2H) precursors to Streptomyces capreolus A250. These studies indicated that the 2,3-diaroinopropionate (Dap) moiety of capreomycin is derived from serine via a dehydroalanyl intermediate. The very high incorporation of labeled serine specifically into the serine moiety of capreomycin IA, 1, and incorporation of labeled alanine into the alanine moiety of capreomycin IB, 2, revealed that neither 1 nor 2 is converted into the other. Deuteriated 2,3-diaminopropionic acid was incorporated specifically into the Dap and Δ2,3-ureido-Dap residues, demonstrating that it is an intermediate in the biosynthesis of capreomycin and revealing that the pathway involves prepeptide assembly modification of serine.

Original languageEnglish (US)
Pages (from-to)5176-5180
Number of pages5
JournalJournal of Organic Chemistry
Volume58
Issue number19
DOIs
StatePublished - Jan 1 1993

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ASJC Scopus subject areas

  • Organic Chemistry

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