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


Schmartz, Patrick; Wölfel, Katharina; Zerbe, Katja; Gad, Emad; El Tamany, El Sayed; Ibrahim, Hassen K; Abou-Hadeed, Khaled; Robinson, John A (2012). Substituent effects on the phenol coupling reaction catalyzed by the vancomycin biosynthetic P450 enzyme OxyB. Angewandte Chemie Internationale Edition, 51:11468-11472.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:October 2012
Deposited On:10 Jan 2013 10:18
Last Modified:16 Jan 2017 08:22
Publisher:Wiley-VCH Verlag
ISSN:1433-7851
Funders:Swiss National Science Foundation
Publisher DOI:https://doi.org/10.1002/anie.201204458
PubMed ID:23073849

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