Biosynthesis of streptothricin F. 5. Formation of .beta.-lysine by Streptomyces L-1689-23

Autor:	T. K. Thiruvengadam, Horng-Jau Lin, D. J. Aberhart, S. J. Gould
Rok vydání:	1983
Předmět:	chemistry.chemical_classification biology Stereochemistry Chemistry Lysine General Chemistry Carbon-13 NMR biology.organism_classification Biochemistry Streptomyces Catalysis Amino acid NMR spectra database chemistry.chemical_compound Colloid and Surface Chemistry Biosynthesis Proton NMR Moiety
Zdroj:	Journal of the American Chemical Society. 105:5470-5476
ISSN:	1520-5126 0002-7863
DOI:	10.1021/ja00354a047
Popis:	The formation of the ..beta..-lysine moiety of streptothricin F has been studied by feeding to Streptomyces L-1689-23 ..cap alpha..-(3-/sup 13/C,/sup 15/N)-, ..cap alpha..-((3RS)-/sup 2/H/sub 2/)-, ..cap alpha..-((3R)-/sup 2/H)-, and ..cap alpha..-((3S)-/sup 2/H)lysine and ..beta..-((2S)-/sup 2/H)lysine. From the analysis of either the /sup 13/C NMR or /sup 2/H NMR spectrum of the derived antibiotics, it has been determined that the ..cap alpha..-nitrogen migrates to C-3 with inversion of configuration by an intramolecular process, and the 3-pro-R hydrogen migrates to C-2 with inversion of configuration by a process that is substantially or completely intermolecular. The very high degree of incorporation of labeled ..beta..-lysine indicates it is probably an intermediate in the biosynthesis of streptothricin F.
Databáze:	OpenAIRE
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