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Regioselectivity and Activity of Cytochrome P450 BM-3 and Mutant F87A in Reactions Driven by Hydrogen Peroxide

Cirino, Patrick C. and Arnold, Frances H. (2002) Regioselectivity and Activity of Cytochrome P450 BM-3 and Mutant F87A in Reactions Driven by Hydrogen Peroxide. Advanced Synthesis and Catalysis, 344 (9). pp. 932-937. ISSN 1615-4150. doi:10.1002/1615-4169(200210)344:9<932::AID-ADSC932>3.0.CO;2-M. https://resolver.caltech.edu/CaltechAUTHORS:20180823-093530127

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Abstract

Cytochrome P450 BM‐3 (EC 1.14.14.1) is a monooxygenase that utilizes NADPH and dioxygen to hydroxylate fatty acids at subterminal positions. The enzyme is also capable of functioning as a peroxygenase in the same reaction, by utilizing hydrogen peroxide in place of the reductase domain, cofactor and oxygen. As a starting point for developing a practically useful hydroxylation biocatalyst, we compare the activity and regioselectivity of wild‐type P450 BM‐3 and its F87A mutant on various fatty acids. Neither enzyme catalyzes terminal hydroxylation under any of the conditions studied. While significantly enhancing peroxygenase activity, the F87A mutation also shifts hydroxylation further away from the terminal position. The H_2O_2‐driven reactions with either the full‐length BM‐3 enzyme or the heme domain are slow, but yield product distributions very similar to those generated when using NADPH and O_2.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/1615-4169(200210)344:9<932::AID-ADSC932>3.0.CO;2-M DOIArticle
ORCID:
AuthorORCID
Cirino, Patrick C.0000-0002-7245-6205
Arnold, Frances H.0000-0002-4027-364X
Additional Information:© 2002 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim. Received: May 14, 2002; Accepted: July 18, 2002. Dedicated to Roger Sheldon on the occasion of his 60th birthday. We thank Dr. Ulrich Schwaneberg and Dr. Edgardo Farinas for helpful advice and assistance and Dr. Nathan Dalleska for assistance with the GC procedures. This work was supported by the Biotechnology Research and Development Corporation (Peoria, IL).
Funders:
Funding AgencyGrant Number
Biotechnology Research and Development CorporationUNSPECIFIED
Subject Keywords:cytochrome P450 BM‐3; enzyme catalysis; fatty acids; hydroxylation; peroxide shunt pathway; peroxygenase; regioselectivity
Issue or Number:9
DOI:10.1002/1615-4169(200210)344:9<932::AID-ADSC932>3.0.CO;2-M
Record Number:CaltechAUTHORS:20180823-093530127
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20180823-093530127
Official Citation:Cirino, P. and Arnold, F. (2002), Regioselectivity and Activity of Cytochrome P450 BM‐3 and Mutant F87A in Reactions Driven by Hydrogen Peroxide. Adv. Synth. Catal., 344: 932-937. doi:10.1002/1615-4169(200210)344:9<932::AID-ADSC932>3.0.CO;2-M
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:89083
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:23 Aug 2018 17:08
Last Modified:16 Nov 2021 00:32

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