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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. http://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:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja061261xDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja061261xPublisherArticle
http://pubs.acs.org/doi/suppl/10.1021/ja061261xPublisherSupporting Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2551755PubMed CentralArticle
ORCID:
AuthorORCID
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 AgencyGrant Number
NSFBES-9981770
NIHR01 GM068664-01
NSF Graduate Research FellowshipUNSPECIFIED
Swedish Foundation for Strategic ResearchUNSPECIFIED
PubMed Central ID:PMC2551755
Record Number:CaltechAUTHORS:20170424-103335679
Persistent URL:http://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
Usage Policy: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:12 Sep 2017 19:50

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