title: Stereoselective hydroxylation of an achiral cyclopentanecarboxylic acid derivative using engineered P450s BM-3.
abstract: Substrate engineered, achiral carboxylic acid derivative was biohydroxylated with various mutants of cytochrome P450 BM-3 to give two out of the four possible diastereoisomers in high de and ee. The BM-3 mutants exhibit up to 9200 total turnovers for hydroxylation of the engineered substrate, which without the protecting group is not transformed by this enzyme.
authors.affiliation: Institut für Organische Chemie der Technischen Universität Graz, Austria.
authors.forename: Dieter F
authors.initials: DF
authors.lastname: Münzer
authors.forename: Peter
authors.initials: P
authors.lastname: Meinhold
authors.forename: Matthew W
authors.initials: MW
authors.lastname: Peters
authors.forename: Sabine
authors.initials: S
authors.lastname: Feichtenhofer
authors.forename: Herfried
authors.initials: H
authors.lastname: Griengl
authors.forename: Frances H
authors.initials: FH
authors.lastname: Arnold
authors.forename: Anton
authors.initials: A
authors.lastname: Glieder
authors.forename: Anna
authors.initials: A
authors.lastname: de Raadt
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry*; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry*; D006900:Hydroxylation; D006899:Mixed Function Oxygenases / Q000737:chemistry*; D008968:Molecular Conformation; D009251:NADPH-Ferrihemoprotein Reductase; D015202:Protein Engineering / Q000379:methods*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001426:Bacterial Proteins; D002264:Carboxylic Acids; D003517:Cyclopentanes; D003577:Cytochrome P-450 Enzyme System; D006899:Mixed Function Oxygenases; D009251:NADPH-Ferrihemoprotein Reductase; C052423:flavocytochrome P450 BM3 monoxygenases