The Biosynthesis of Indolmycin

U. Hornemann, L. H. Hurley, M. K. Speedie, H. G. Floss

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

Indolmycin, an antibiotic produced by a strain of Streptomycesgriseus, is formed from (S)-tryptophan, which loses from its side chain the amino nitrogen atom, the hydrogen atom from C-2, and one of the hydrogen atoms from C-3, two intact methyl groups of (β-methionine, and the guanido carbon atom of (S)-arginine. (R)-β-Methylindolepyruvate and (2S,3R)-indolmycenic acid are intermediates in the biosynthesis. The absolute configuration of indolmycin has been determined by chemical correlation with (-)-(R)-indoleisopropionic acid. Studies with cell-free extracts of 5. griseus revealed the presence of a transaminase which converts (S)-tryptophan into indolepyruvate and a methyltransferase which C-methylates indolepyruvate.

Original languageEnglish (US)
Pages (from-to)3028-3035
Number of pages8
JournalJournal of the American Chemical Society
Volume93
Issue number12
DOIs
StatePublished - Jun 1 1971

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