The biosynthesis of indolmycin

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

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

Indolmycin, an antibiotic produced by a strain of Streptomyces griseus, 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 (S)-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 S. 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
StatePublished - 1971
Externally publishedYes

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Streptomyces griseus
Biosynthesis
Tryptophan
Hydrogen
Atoms
Acids
Transaminases
Cell Extracts
Methionine
Arginine
Nitrogen
Carbon
Anti-Bacterial Agents
Methyltransferases
Antibiotics
indolmycin
indolepyruvate methyltransferase

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Hornemann, U., Hurley, L., Speedie, M. K., & Floss, H. G. (1971). The biosynthesis of indolmycin. Journal of the American Chemical Society, 93(12), 3028-3035.

The biosynthesis of indolmycin. / Hornemann, U.; Hurley, Laurence; Speedie, M. K.; Floss, H. G.

In: Journal of the American Chemical Society, Vol. 93, No. 12, 1971, p. 3028-3035.

Research output: Contribution to journalArticle

Hornemann, U, Hurley, L, Speedie, MK & Floss, HG 1971, 'The biosynthesis of indolmycin', Journal of the American Chemical Society, vol. 93, no. 12, pp. 3028-3035.
Hornemann U, Hurley L, Speedie MK, Floss HG. The biosynthesis of indolmycin. Journal of the American Chemical Society. 1971;93(12):3028-3035.
Hornemann, U. ; Hurley, Laurence ; Speedie, M. K. ; Floss, H. G. / The biosynthesis of indolmycin. In: Journal of the American Chemical Society. 1971 ; Vol. 93, No. 12. pp. 3028-3035.
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