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The Biosynthesis of Vancomycin‐Type Glycopeptide Antibiotics—A Model for Oxidative Side‐Chain Cross‐Linking by Oxygenases Coupled to the Action of Peptide Synthetases
Author(s) -
Bischoff Daniel,
Bister Bojan,
Bertazzo Marcelo,
Pfeifer Volker,
Stegmann Efthimia,
Nicholson Graeme J.,
Keller Simone,
Pelzer Stefan,
Wohlleben Wolfgang,
Süssmuth Roderich D.
Publication year - 2005
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.200400328
Subject(s) - nonribosomal peptide , glycopeptide , biosynthesis , peptide , biochemistry , mutant , chemistry , oxidative phosphorylation , monooxygenase , glycopeptide antibiotic , antibiotics , stereochemistry , biology , vancomycin , gene , enzyme , bacteria , cytochrome p450 , genetics , staphylococcus aureus
Model mutants . The biosynthesis of glycopeptide antibiotics must be understood before it can be reprogrammed to generate altered antibiotics. Based on a detailed HPLC‐ESI‐MS analysis of linear and cyclic peptide intermediates of balhimycin biosynthesis mutants, a new model for glycopeptide assembly is suggested (see figure). We propose that the three central oxidative cyclizations by P450‐dependant monooxygenases occur during peptide assembly before cleavage from the nonribosomal peptide synthetase complex.