Biosynthesis of blasticidin S from L-.alpha.-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction

A series of labeled alpha -arginines have been fed to fermentations of Streptomyces griseochromogenes in order to examine the mechanism of L- beta -arginine formation in the biosynthesis of the antibiotic blasticidin S. (3- super(13)C,2- super(15)N)Arginine was synthesized and fed; analysis of the d...

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Veröffentlicht in:Journal of the American Chemical Society 1988-08, Vol.110 (17), p.5785-5791
Hauptverfasser: Prabhakaran, P. C, Woo, Nam Tae, Yorgey, Peter S, Gould, Steven J
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container_end_page 5791
container_issue 17
container_start_page 5785
container_title Journal of the American Chemical Society
container_volume 110
creator Prabhakaran, P. C
Woo, Nam Tae
Yorgey, Peter S
Gould, Steven J
description A series of labeled alpha -arginines have been fed to fermentations of Streptomyces griseochromogenes in order to examine the mechanism of L- beta -arginine formation in the biosynthesis of the antibiotic blasticidin S. (3- super(13)C,2- super(15)N)Arginine was synthesized and fed; analysis of the derived antibiotic by super(13)C NMR spectroscopy revealed the retention of the original alpha -nitrogen and its intramolecular migration to the beta -position, revealing the presence of an arginine-2,3-aminomutase.
doi_str_mv 10.1021/ja00225a033
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subjects Antibiotics (antibacterial agents, antifungal agents)
Antibiotics, microbial producers, chemotherapic agents, antiseptics, disinfecting agents
Applied microbiology
Biological and medical sciences
Biology of microorganisms of confirmed or potential industrial interest
Biotechnology
Fundamental and applied biological sciences. Psychology
Microbiology
Mission oriented research
Physiology and metabolism
Streptomyces griseochromogenes
title Biosynthesis of blasticidin S from L-.alpha.-arginine. Stereochemistry in the arginine-2,3-aminomutase reaction
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