Conversion of (2S)‐Arginine to (2S,3R)‐Capreomycidine by VioC and VioD from the Viomycin Biosynthetic Pathway of Streptomyces sp. Strain ATCC11861

The nonproteinogenic amino acid (2S,3R)-capreomycidine is an essential component of the tuberactinomycin family of antibiotics and is derived from the unusual intramolecular cyclization of the side chain of (2S)-arginine. The work presented here shows how two enzymes from the viomycin biosynthetic pathway, VioC and VioD, catalyze the stepwise conversion of (2S)-arginine to (3S)-hydroxy-(2S)-arginine to (2S,3R)-capreomycidine. This work establishes the enzymatic steps for the formation of this novel nonproteinogenic amino acid.