Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450BM3 from Bacillus megaterium

Ayhan Çelik; Davide Sperandio; Robert E. Speight; Nicholas J. Turner

doi:10.1039/B506155E

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Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450_BM3 from Bacillus megaterium†

Ayhan Çelik,^a Davide Sperandio,^a Robert E. Speight^a and Nicholas J. Turner*^a

Author affiliations

* Corresponding authors

^a School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh, UK
E-mail: n.j.turner@ed.ac.uk

Abstract

Cytochrome P450_BM3, from Bacillus megaterium, catalyses the epoxidation of linolenic acid 1 yielding 15,16-epoxyoctadeca-9,12-dienoic acid 2 with complete regio- and moderate enantio-selectivity (60% ee). The absolute configuration of the product is tentatively assigned as 15(R),16(S)-. The Michaelis–Menten parameters k_cat and K_m for the reaction were determined to be 3126 ± 226 min⁻¹ and 24 ± 6 μM respectively.

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Supplementary files

Detailed descriptions of experimental procedures, analysis and characterization for compound 2 PDF (133K)

Article information

DOI: https://doi.org/10.1039/B506155E
Article type: Communication
Submitted: 03 May 2005
Accepted: 23 May 2005
First published: 16 Jun 2005

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Org. Biomol. Chem., 2005,3, 2688-2690

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Enantioselective epoxidation of linolenic acid catalysed by cytochrome P450_BM3 from Bacillus megaterium

A. Çelik, D. Sperandio, R. E. Speight and N. J. Turner, Org. Biomol. Chem., 2005, 3, 2688 DOI: 10.1039/B506155E

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Organic & Biomolecular Chemistry