Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism beyond the Protein Matrix

被引：115

作者：

Hoffmann, Alexander ^{[1
,2
]}

Citek, Cooper ^{[3
]}

Binder, Stephan ^{[4
,5
]}

Goos, Arne ^{[4
,5
]}

Ruebhausen, Michael ^{[4
,5
]}

Troeppner, Oliver ^{[6
]}

Ivanovic-Burmazovic, Ivana ^{[6
]}

Wasinger, Erik C. ^{[7
]}

Stack, T. Daniel P. ^{[3
]}

Herres-Pawlis, Sonja ^{[1
,2
]}

机构：

[1] Univ Munich, Dept Chem, D-81377 Munich, Germany

[2] Tech Univ Dortmund, Fak Chem, D-44227 Dortmund, Germany

[3] Stanford Univ, Dept Chem, Stanford, CA 94305 USA

[4] Univ Hamburg, Inst Appl Phys, Hamburg, Germany

[5] Univ Hamburg, Ctr Free Electron Laser, Hamburg, Germany

[6] Univ Erlangen Nurnberg, Dept Chem & Pharm, Nurnberg, Germany

[7] Calif State Univ Chico, Dept Chem & Biochem, Chico, CA 95929 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 20期

基金：

美国国家卫生研究院;

关键词：

bioinorganic chemistry; copper; dioxygen; homogeneous catalysis; tyrosinase; MODEL SYSTEM; PEROXODICOPPER(II) COMPLEX; COPPER(I) COMPLEX; BINDING; OXYGENATION; REACTIVITY; CATECHOLS; LIGAND; SUBSTRATE; INSIGHT;

D O I：

10.1002/anie.201301249

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A new catalyst (see structure) hydroxylates phenols with O2 via a stable side-on peroxide complex, which is similar to the active site of tyrosinase in terms of the ligand environment and its spectroscopic properties. The catalytic oxidation of phenols to quinones proceeds at room temperature in the presence of NEt3 and even non-native substrates can be oxidized catalytically. The reaction mechanism is analogous to that of the enzyme-catalyzed reaction. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：5398 / 5401

页数：4

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