title: Biocatalytic route to chiral acyloins: P450-catalyzed regio- and enantioselective α-hydroxylation of ketones.
abstract: P450-BM3 and mutants of this monooxygenase generated by directed evolution are excellent catalysts for the oxidative α-hydroxylation of ketones with formation of chiral acyloins with high regioselectivity (up to 99%) and enantioselectivity (up to 99% ee). This constitutes a new route to a class of chiral compounds that are useful intermediates in the synthesis of many kinds of biologically active compounds.
authors.affiliation: Department of Chemistry, Philipps-Universität Marburg , Hans-Meerwein Strasse, 35032 Marburg, Germany.
authors.forename: Rubén
authors.initials: R
authors.lastname: Agudo
authors.forename: Gheorghe-Doru
authors.initials: GD
authors.lastname: Roiban
authors.forename: Richard
authors.initials: R
authors.lastname: Lonsdale
authors.forename: Adriana
authors.initials: A
authors.lastname: Ilie
authors.forename: Manfred T
authors.initials: MT
authors.lastname: Reetz
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry* / Q000378:metabolism; D055162:Biocatalysis; D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry* / Q000378:metabolism; D005233:Fatty Alcohols; D006900:Hydroxylation; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D009251:NADPH-Ferrihemoprotein Reductase / Q000737:chemistry* / Q000378:metabolism; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D001426:Bacterial Proteins; D001688:Biological Products; D005233:Fatty Alcohols; D007659:Ketones; C011159:acyloin; D003577:Cytochrome P-450 Enzyme System; D009251:NADPH-Ferrihemoprotein Reductase; C052423:flavocytochrome P450 BM3 monoxygenases