Bioinorganic Chemistry and Applications 
Volume 2008 (2008), Article ID 762029, 9 pages
doi:10.1155/2008/762029
Research Article

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

Francesco G. Mutti, Roberta Pievo, Maila Sgobba, Michele Gullotti, and Laura Santagostini

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

Recommended by Marc Fontecave

Abstract

The biomimetic catalytic oxidations of the dinuclear and trinuclear copper(II) complexes versus two catechols, namely, D-(+)-catechin and L-()-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 D-(+)-catechin to respect the other catechol, because of the spatial disposition of this substrate.