New catalytic model systems of tyrosinase: fine tuning of the reactivity with pyrazole-based N-donor ligands

被引：60

作者：

Hamann, Jessica Nadine ^{[1
]}

Tuczek, Felix ^{[1
]}

机构：

[1] Univ Kiel, D-24118 Kiel, Germany

来源：

CHEMICAL COMMUNICATIONS | 2014年 / 50卷 / 18期

关键词：

CRYSTAL-STRUCTURE; HYDROXYLATION; MECHANISM; COMPLEXES; KINETICS;

D O I：

10.1039/c3cc47888b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two new Cu(I) complexes have been synthesized and investigated as model systems of the enzyme tyrosinase. The corresponding ligands are based on a combination of an imine function with two different pyrazole groups. The reactivity of the prepared systems with respect to the conversion of monophenols to the corresponding orthoquinones is investigated. The resulting data are compared to results obtained for other catalytic model systems of tyrosinase.

引用

收藏

页码：2298 / 2300

页数：3

相关论文

共 25 条

[1] MODEL MONOOXYGENASE REACTIVITY BY BINUCLEAR 2-COORDINATE COPPER(I) COMPLEXES EXTENDS TO NEW LIGAND SYSTEMS CONTAINING NITROGEN AND SULFUR DONORS [J].

CASELLA, L ;

GULLOTTI, M ;

BARTOSEK, M ;

PALLANZA, G ;

LAURENTI, E .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (18) :1235-1237

[2] Modeling tyrosinase activity. Effect of ligand topology on aromatic ring hydroxylation: An overview [J].

De, Anindita ;

Mandal, Sukanta ;

Mukherjee, Rabindranath .

JOURNAL OF INORGANIC BIOCHEMISTRY, 2008, 102 (5-6) :1170-1189

[3] The first crystal structure of tyrosinase: All questions answered? [J].

Decker, Heinz ;

Schweikardt, Thorsten ;

Tuczek, Felix .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (28) :4546-4550

[4]

Eicken C., 2001, HDB METALLOPROTEINS, V2, P1319

[5] UBER ULTRAVIOLETTSPEKTREN EINIGER BENZOCHINONE [J].

FLAIG, W ;

PLOETZ, T ;

KULLMER, A .

ZEITSCHRIFT FUR NATURFORSCHUNG PART B-CHEMIE BIOCHEMIE BIOPHYSIK BIOLOGIE UND VERWANDTEN GEBIETE, 1955, 10 (12) :668-676

[6] Catalytic Phenol Hydroxylation with Dioxygen: Extension of the Tyrosinase Mechanism beyond the Protein Matrix [J].

Hoffmann, Alexander ;

Citek, Cooper ;

Binder, Stephan ;

Goos, Arne ;

Ruebhausen, Michael ;

Troeppner, Oliver ;

Ivanovic-Burmazovic, Ivana ;

Wasinger, Erik C. ;

Stack, T. Daniel P. ;

Herres-Pawlis, Sonja .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) :5398-5401

[7] Crystal Structure of Agaricus bisporus Mushroom Tyrosinase: Identity of the Tetramer Subunits and Interaction with Tropolone [J].

Ismaya, Wangsa T. ;

Rozeboom, Henriette J. ;

Weijn, Amrah ;

Mes, Jurriaan J. ;

Fusetti, Fabrizia ;

Wichers, Harry J. ;

Dijkstra, Bauke W. .

BIOCHEMISTRY, 2011, 50 (24) :5477-5486

[8] Kinetics and thermodynamics of copper(I)/dioxygen interaction [J].

Karlin, KD ;

Kaderli, S ;

Zuberbuhler, AD .

ACCOUNTS OF CHEMICAL RESEARCH, 1997, 30 (03) :139-147

[9] COPPER-MEDIATED HYDROXYLATION OF AN ARENE - MODEL SYSTEM FOR THE ACTION OF COPPER MONOOXYGENASES - STRUCTURES OF A BINUCLEAR CU(I) COMPLEX AND ITS OXYGENATED PRODUCT [J].

KARLIN, KD ;

HAYES, JC ;

GULTNEH, Y ;

CRUSE, RW ;

MCKOWN, JW ;

HUTCHINSON, JP ;

ZUBIETA, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (07) :2121-2128

[10]

Kenji K., 2010, Jp. Pat, Patent No. [2010-215610, 2010215610]