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Regio- and Enantioselective Alkane Hydroxylation with Engineered Cytochromes P450 BM-3

Peters, Matthew W. and Meinhold, Peter and Glieder, Anton and Arnold, Frances H. (2003) Regio- and Enantioselective Alkane Hydroxylation with Engineered Cytochromes P450 BM-3. Journal of the American Chemical Society, 125 (44). pp. 13442-13450. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170515-134122486

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Abstract

Cytochrome P450 ΒΜ-3 from Bacillus megaterium was engineered using a combination of directed evolution and site-directed mutagenesis to hydroxylate linear alkanes regio- and enantioselectively using atmospheric dioxygen as an oxidant. BM-3 variant 9-10A-A328V hydroxylates octane at the 2-position to form S-2-octanol (40% ee). Another variant, 1-12G, also hydroxylates alkanes larger than hexane primarily at the 2-position but forms R-2-alcohols (40−55% ee). These biocatalysts are highly active (rates up to 400 min-1) and support thousands of product turnovers. The regio- and enantioselectivities are retained in whole-cell biotransformations with Escherichia coli, where the engineered P450s can be expressed at high levels and the cofactor is supplied endogenously.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja0303790DOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja0303790UNSPECIFIEDArticle
ORCID:
AuthorORCID
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2003 American Chemical Society. Received 24 June 2003. Published online 11 October 2003. Published in print 1 November 2003. The authors thank Dr. Nathan Dalleska for his assistance with the gas chromatography. This work is supported by the National Science Foundation (BES-9981770).
Funders:
Funding AgencyGrant Number
NSFBES-9981770
Issue or Number:44
Record Number:CaltechAUTHORS:20170515-134122486
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170515-134122486
Official Citation:Regio- and Enantioselective Alkane Hydroxylation with Engineered Cytochromes P450 BM-3 Matthew W. Peters, Peter Meinhold, Anton Glieder, and Frances H. Arnold Journal of the American Chemical Society 2003 125 (44), 13442-13450 DOI: 10.1021/ja0303790
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:77460
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:16 May 2017 03:32
Last Modified:03 Oct 2019 17:57

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