title: Asymmetric Ketone Reduction by Imine Reductases.
abstract: The rapidly growing area of asymmetric imine reduction by imine reductases (IREDs) has provided alternative routes to chiral amines. Here we report the expansion of the reaction scope of IREDs by showing the stereoselective reduction of 2,2,2-trifluoroacetophenone. Assisted by an in silico analysis of energy barriers, we evaluated asymmetric hydrogenations of carbonyls and imines while considering the influence of substrate reactivity on the chemoselectivity of this novel class of reductases. We report the asymmetric reduction of C=N as well as C=O bonds catalysed by members of the IRED enzyme family.
authors.affiliation: Institute of Technical Biochemistry, Universitaet Stuttgart, Allmandring 31, 70569, Stuttgart, Germany.
authors.forename: Maike
authors.initials: M
authors.lastname: Lenz
authors.affiliation: Institute for Theoretical Chemistry, Universitaet Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany.
authors.forename: Jan
authors.initials: J
authors.lastname: Meisner
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia, 30322, USA.
authors.forename: Leann
authors.initials: L
authors.lastname: Quertinmont
authors.affiliation: Department of Chemistry, Emory University, 1515 Dickey Drive, Atlanta, Georgia, 30322, USA.
authors.forename: Stefan
authors.initials: S
authors.lastname: Lutz
authors.affiliation: Institute for Theoretical Chemistry, Universitaet Stuttgart, Pfaffenwaldring 55, 70569, Stuttgart, Germany.
authors.forename: Johannes
authors.initials: J
authors.lastname: Kästner
authors.affiliation: Institute of Technical Biochemistry, Universitaet Stuttgart, Allmandring 31, 70569, Stuttgart, Germany.
authors.forename: Bettina M
authors.initials: BM
authors.lastname: Nestl
mesh_terms: D001426:Bacterial Proteins / Q000737:chemistry / Q000378:metabolism*; D055162:Biocatalysis; D007097:Imines / Q000737:chemistry / Q000378:metabolism; D007659:Ketones / Q000737:chemistry / Q000378:metabolism*; D009249:NADP / Q000737:chemistry / Q000378:metabolism; D010088:Oxidoreductases / Q000737:chemistry / Q000378:metabolism*; D056507:Paenibacillus / Q000201:enzymology; D013302:Streptomyces / Q000201:enzymology; D013816:Thermodynamics
chemical_list: D001426:Bacterial Proteins; D007097:Imines; D007659:Ketones; D009249:NADP; D010088:Oxidoreductases
keywords: asymmetric catalysis; biocatalysis; carbonyl compounds; promiscuity; reduction