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

Summary: Enantioselective r-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. Ba¨ckvall, and
Frances H. Arnold*,
DiVision of Chemistry and Chemical Engineering 210-41, California Institute of Technology, Pasadena, California
91125-4100, U.S.A., and Department of Organic Chemistry, Arrhenius Laboratory, Stockholm UniVersity, SE-106
91 Stockholm, Sweden.
Received February 22, 2006;; E-mail: frances@cheme.caltech.edu
Biocatalytic processes are becoming increasingly important in
organic synthesis1 due to their unique selectivity advantages over
conventional methods.2,3 Common biocatalytic transformations
include enantioselective transesterification,4 reduction of ketones,2
Baeyer-Villiger oxidation,5 and epoxide opening.6 Recently, bio-
catalytic hydroxylations have attracted considerable interest.7,8 Here,
we report a variant of cytochrome P450 BM-3 (BM-3; isolated from
Bacillus megaterium) capable of efficient and highly enantioselec-
tive hydroxylation at the alpha position of certain carboxylic and
peptide groups.
BM-3 is a well-studied, NADPH-dependent monooxygenase that
hydroxylates long-chain fatty acids at the -1, -2, and -3

  

Source: Arnold, Frances H. - Division of Chemistry and Chemical Engineering, California Institute of Technology

 

Collections: Chemistry; Biology and Medicine