Substituent effects on the phenol coupling reaction catalyzed by the vancomycin biosynthetic P450 enzyme OxyB

Abstract

Oxidative phenol coupling reactions are required to establish the cross-linked heptapeptide backbone of vancomycin. The first cross-linking reaction, catalyzed by the P450 enzyme OxyB, is dramatically slower when a chlorine substituent is present in the hexapeptide-S-PCP substrate and is abolished when chlorine is introduced into a potential heptapeptide-S-PCP substrate