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Substituent Effects on the Phenol Coupling Reaction Catalyzed by the Vancomycin Biosynthetic P450 Enzyme OxyB
Author(s) -
Schmartz Patrick C.,
Wölfel Katharina,
Zerbe Katja,
Gad Emad,
El Tamany El Sayed,
Ibrahim Hassen K.,
AbouHadeed Khaled,
Robinson John A.
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201204458
Subject(s) - substituent , chemistry , substrate (aquarium) , phenol , enzyme , catalysis , oxidative phosphorylation , chlorine , coupling reaction , oxidative coupling of methane , stereochemistry , combinatorial chemistry , biochemistry , organic chemistry , biology , ecology
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.
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