NDLI: Spectroscopic and Mechanistic Studies on Oxidation Reactions Catalyzed by the Functional Model SR Complex for Cytochrome P450: Influence of Oxidant, Substrate, and Solvent

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Spectroscopic and Mechanistic Studies on Oxidation Reactions Catalyzed by the Functional Model SR Complex for Cytochrome P450: Influence of Oxidant, Substrate, and Solvent

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Hessenauer-ilicheva, Natalya Wolak, Maria Franke, Alicja Higuchi, Tsunehiko Van Eldik, Rudi
Description	Author Affiliation: Hessenauer-Ilicheva N ( Inorganic Chemistry, Department of Chemistry and Pharmacy, Egerlandstrasse 1, 91058 Erlangen, Germany.)
Abstract	Kinetic and mechanistic studies on the formation of an oxoiron(IV) porphyrin cation radical bearing a thiolate group as proximal ligand are reported. The SR complex, a functional enzyme mimic of P450, was oxidized in peroxo-shunt reactions under different experimental conditions with variation of solvent, temperature, and identity and excess of oxidant in the presence of different organic substrates. Through the application of a low-temperature rapid-scan stopped-flow technique, the reactive intermediates in the SR catalytic cycle, such as the initially formed SR acylperoxoiron(III) complex and the SR high-valent iron(IV) porphyrin cation radical complex $[(SR^{.+})Fe^{IV}O],$ were successfully identified and kinetically characterized. The oxidation of the SR complex under catalytic conditions provided direct spectroscopic information on the reactivity of $[(SR^{.+})Fe^{IV}O]$ towards the oxidation of selected organic substrates. Because the catalytically active species is a synthetic oxoiron(IV) porphyrin cation radical bearing a thiolate proximal group, the effect of the strong electron donor ligand on the formation and reactivity/stability of the SR high-valent iron species is addressed and discussed in the light of the reactivity pattern observed in substrate oxygenation reactions catalyzed by native P450 enzyme systems.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	45
Volume Number	15
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2009-11-16
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Cations Chemistry Cytochrome P-450 Enzyme System Metalloporphyrins Oxidants Catalysis Metabolism Kinetics Ligands Models, Chemical Oxidation-Reduction Solvents Spectrum Analysis, Raman Substrate Specificity Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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