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Enantioselective Epoxidation of Terminal Alkenes to (R)- and (S)-Epoxides by Engineered Cytochromes P450 BM-3

Kubo, Takafumi and Peters, Matthew W. and Meinhold, Peter and Arnold, Frances H. (2006) Enantioselective Epoxidation of Terminal Alkenes to (R)- and (S)-Epoxides by Engineered Cytochromes P450 BM-3. Chemistry: a European Journal, 12 (4). pp. 1216-1220. ISSN 0947-6539. https://resolver.caltech.edu/CaltechAUTHORS:20180821-153046657

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Abstract

Cytochrome P450 BM‐3 from Bacillus megaterium was engineered for enantioselective epoxidation of simple terminal alkenes. Screening saturation mutagenesis libraries, in which mutations were introduced in the active site of an engineered P450, followed by recombination of beneficial mutations generated two P450 BM‐3 variants that convert a range of terminal alkenes to either (R)‐ or (S)‐epoxide (up to 83 % ee) with high catalytic turnovers (up to 1370) and high epoxidation selectivities (up to 95 %). A biocatalytic system using E. coli lysates containing P450 variants as the epoxidation catalysts and in vitro NADPH regeneration by the alcohol dehydrogenase from Thermoanaerobium brockii generates each of the epoxide enantiomers, without additional cofactor.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/chem.200500584DOIArticle
ORCID:
AuthorORCID
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2006 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Received: May 26, 2005; Published online: October 20, 2005. The authors thank Dr. Nathan Dalleska for assistance with gas chromatography. This work is supported by the National Science Foundation (BES-0313567), the Donors of the American Chemical Society Petroleum Research Fund (ACS PRF Alternative Energy Postdoctoral Fellowship for MWP) and the Nippon Shokubai Co., Ltd.
Funders:
Funding AgencyGrant Number
NSFBES-0313567
American Chemical Society Petroleum Research FundUNSPECIFIED
Nippon Shokubai Co., Ltd.UNSPECIFIED
Subject Keywords:alkenes; biocatalysis; cofactors; cytochrome p450; enantioselectivity; epoxidation
Issue or Number:4
Record Number:CaltechAUTHORS:20180821-153046657
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180821-153046657
Official Citation:Kubo, T. , Peters, M. W., Meinhold, P. and Arnold, F. H. (2006), Enantioselective Epoxidation of Terminal Alkenes to (R)‐ and (S)‐Epoxides by Engineered Cytochromes P450 BM‐3. Chemistry – A European Journal, 12: 1216-1220. doi:10.1002/chem.200500584
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:88995
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:21 Aug 2018 22:48
Last Modified:03 Oct 2019 20:12

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