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.
Biomimetic modeling of copper complexes : a study of enantioselective catalytic oxidation on D-(+)-catechin and L-(–)-epicatechin with copper complexes / F. G. Mutti, R. Pievo, M. Sgobba, M. Gullotti, L. Santagostini. - In: BIOINORGANIC CHEMISTRY AND APPLICATIONS. - ISSN 1565-3633. - 2008(2008), p. 762029.article n. 762029.
Biomimetic modeling of copper complexes : a study of enantioselective catalytic oxidation on D-(+)-catechin and L-(–)-epicatechin with copper complexes
F. G. MuttiPrimo
;R. PievoSecondo
;M. Sgobba;M. GullottiPenultimo
;L. SantagostiniUltimo
2008
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.Pubblicazioni consigliate
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