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Bioinorganic Chemistry and Applications
Volume 2008, Article ID 762029, 9 pages
http://dx.doi.org/10.1155/2008/762029
Research Article

Biomimetic Modeling of Copper Complexes: A Study of Enantioselective Catalytic Oxidation on -(+)-Catechin and -()-Epicatechin with Copper Complexes

Dipartimento di Chimica Inorganica, Metallorganica e Analitica “Lamberto Malatesta”, Università di Milano, Istituto ISTM-CNR, Via Venezian 21, 20133 Milano, Italy

Received 21 March 2008; Revised 30 May 2008; Accepted 11 August 2008

Academic Editor: Marc Fontecave

Copyright © 2008 Francesco G. Mutti et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The biomimetic catalytic oxidations of the dinuclear and trinuclear copper(II) complexes versus two catechols, namely, -(+)-catechin and -()-epicatechin to give the corresponding quinones are reported. The unstable quinones were trapped by the nucleophilic reagent, 3-methyl-2-benzothiazolinone hydrazone (MBTH), and have been calculated the molar absorptivities of the different quinones. The catalytic efficiency is moderate, as inferred by kinetic constants, but the complexes exhibit significant enantio-differentiating ability towards the catechols, albeit for the dinuclear complexes, this enantio-differentiating ability is lower. In all cases, the preferred enantiomeric substrate is -(+)-catechin to respect the other catechol, because of the spatial disposition of this substrate.