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Conversion of (2 S )‐Arginine to (2 S ,3 R )‐Capreomycidine by VioC and VioD from the Viomycin Biosynthetic Pathway of Streptomyces sp. Strain ATCC11861
Author(s) -
Ju Jianhua,
Ozanick Sarah G.,
Shen Ben,
Thomas Michael G.
Publication year - 2004
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200400136
Subject(s) - viomycin , stereochemistry , arginine , enzyme , amino acid , biochemistry , biosynthesis , intramolecular force , chemistry , polyketide , strain (injury) , biology , antibiotics , streptomycin , anatomy
The nonproteinogenic amino acid (2 S ,3 R )‐capreomycidine is an essential component of the tuberactinomycin family of antibiotics and is derived from the unusual intramolecular cyclization of the side chain of (2 S )‐arginine. The work presented here shows how two enzymes from the viomycin biosynthetic pathway, VioC and VioD, catalyze the stepwise conversion of (2 S )‐arginine to (3 S )‐hydroxy‐(2 S )‐arginine to (2 S ,3 R )‐capreomycidine. This work establishes the enzymatic steps for the formation of this novel nonproteinogenic amino acid.