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
Format:	Artikel
Sprache:	eng
Schlagworte:	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
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Zusammenfassung:	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.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja00225a033