U. Mocek, Zhaopie Zeng, D. O'Hagan
Sep 1, 1993
Citations
3
Influential Citations
97
Citations
Quality indicators
Journal
Journal of the American Chemical Society
Abstract
The biosynthesis of the thiopeptide antibiotic thiostrepton (1) has been investigated by administration of isotopically labeled precursors to cultures of Streptomyces azureus and Streptomyces laurentii. The amino acid origin of all the components of the antibiotic was demonstrated. Experiments with (S)-[1,2- 13 C 2 ]- and (S)-[2,3- 13 C 2 ]serine showed intact incorporation of serine into the thiazoline and thiazole rings as well as the dehydroalanine, alanine, and tetrahydropyridine moieties. (S)-[3- 13 C, 2 H 2 ]Serine and (2S,3S)-[3- 13 C, 2 H 1 ]serine were used to elucidate the stereochemistry of the various transformations of serine