Enantioselective α-Hydroxylation of 2-Arylacetic Acid Derivatives and Buspirone Catalyzed by Engineered Cytochrome P450 BM-3

Landwehr, Marco and Hochrein, Lisa and Otey, Christopher R. and Kasrayan, Alex and Bäckvall, Jan-E. and Arnold, Frances H. (2006) Enantioselective α-Hydroxylation of 2-Arylacetic Acid Derivatives and Buspirone Catalyzed by Engineered Cytochrome P450 BM-3. Journal of the American Chemical Society, 128 (18). pp. 6058-6059. ISSN 0002-7863. PMCID PMC2551755. doi:10.1021/ja061261x. https://resolver.caltech.edu/CaltechAUTHORS:20170424-103335679

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Abstract

Here we report that an engineered microbial cytochrome P450 BM-3 (CYP102A subfamily) efficiently catalyzes the α-hydroxylation of phenylacetic acid esters. This P450 BM-3 variant also produces the authentic human metabolite of buspirone, R-6-hydroxybuspirone, with 99.5% ee.

Item Type:

Article

Related URLs:

URL	URL Type	Description
http://dx.doi.org/10.1021/ja061261x	DOI	Article
http://pubs.acs.org/doi/abs/10.1021/ja061261x	Publisher	Article
http://pubs.acs.org/doi/suppl/10.1021/ja061261x	Publisher	Supporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2551755	PubMed Central	Article

ORCID:

Author	ORCID
Arnold, Frances H.	0000-0002-4027-364X

Additional Information:

© 2006 American Chemical Society. Received February 22, 2006. Publication Date (Web): April 13, 2006. Financial support from the National Science Foundation (BES9981770), NIH Grant R01 GM068664-01, NSF Graduate Research Fellowship program (L.H.), and the Swedish Foundation for Strategic Research (A.K. and J.E.B.) is gratefully acknowledged. Special thanks to N. Dalleska and M. Chen for assistance with the GC, P. Meinhold for cloning the 9-10A-F87A variant, and R. Patel, S. Kiang, and J. Depue (Bristol-Myers Squibb) for assistance with the buspirone analytics.

Funders:

Funding Agency	Grant Number
NSF	BES-9981770
NIH	R01 GM068664-01
NSF Graduate Research Fellowship	UNSPECIFIED
Swedish Foundation for Strategic Research	UNSPECIFIED

Issue or Number:

PubMed Central ID:

PMC2551755

DOI:

10.1021/ja061261x

Record Number:

CaltechAUTHORS:20170424-103335679

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20170424-103335679

Official Citation:

Enantioselective α-Hydroxylation of 2-Arylacetic Acid Derivatives and Buspirone Catalyzed by Engineered Cytochrome P450 BM-3 Marco Landwehr, Lisa Hochrein, Christopher R. Otey, Alex Kasrayan, Jan-E. Bäckvall, and Frances H. Arnold Journal of the American Chemical Society 2006 128 (18), 6058-6059 DOI: 10.1021/ja061261x

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No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

76846

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

24 Apr 2017 20:38

Last Modified:

15 Nov 2021 17:03

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