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Low-temperature rapid-scan detection of reactive intermediates in epoxidation reactions catalyzed by a new enzyme mimic of cytochrome p450

Hessenauer-Ilicheva, Natalya and Franke, Alicja and Meyer, Dominik and Woggon, Wolf-D. and van Eldik, Rudi. (2007) Low-temperature rapid-scan detection of reactive intermediates in epoxidation reactions catalyzed by a new enzyme mimic of cytochrome p450. The journal of the American Chemical Society, Vol. 129, H. 41. pp. 12473-12479.

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Official URL: http://edoc.unibas.ch/dok/A5260126

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Abstract

The use of synthetic iron(III) porphyrins as models for heme-type catalysts in biomimetic cytochrome P 450 research has provided valuable information on the nature and reactivity of intermediates produced in the "peroxide shunt" pathway.  This article reports spectroscopic detection of reactive intermediates formed in the epoxidn. reaction of cis-stilbene with m-chloroperoxybenzoic acid catalyzed by a new mimic of cytochrome P 450 with a substituted RSO3- group (1).  The application of low-temp. rapid-scan stopped-flow techniques enabled the detn. of equil. and rate consts. for the formation and decay of all intermediates in the catalytic cycle of 1, including the rate const. for the formation (1.bul.+)FeIV:O and for oxygen transfer to the substrate.  Noteworthy, the reaction of (1.bul.+)FeIV:O with cis-stilbene leads to an almost complete re-formation (95%) of the starting complex 1.  The results show that complex 1 is a valuable catalyst with promising properties for further applications in a biomimetic approach toward mimicking oxygenation reactions of cytochrome P 450.
Faculties and Departments:05 Faculty of Science
05 Faculty of Science > Departement Chemie > Chemie
UniBasel Contributors:Woggon, Wolf-Dietrich
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:American Chemical Society
ISSN:0002-7863
Note:Publication type according to Uni Basel Research Database: Journal article
Last Modified:22 Mar 2012 14:24
Deposited On:22 Mar 2012 13:42

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