title: Stereoselective reduction of aromatic ketones by a new ketoreductase from Pichia glucozyma.
abstract: A new NADPH-dependent benzil reductase (KRED1-Pglu) was identified from the genome of the non-conventional yeast Pichia glucozyma CBS 5766 and overexpressed in E. coli. The new protein was characterised and reaction parameters were optimised for the enantioselective reduction of benzil to (S)-benzoin. A thorough study of the substrate range of KRED1-Pglu was conducted; in contrast to most other known ketoreductases, KRED1-Pglu prefers space-demanding substrates, which are often converted with high stereoselectivity. A molecular modelling study was carried out for understanding the structural determinants involved in the stereorecognition experimentally observed and unpredictable on the basis of steric properties of the substrates. As a result, a new useful catalyst was identified, enabling the enantioselective preparation of different aromatic alcohols and hydroxyketones.
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Martina Letizia
authors.initials: ML
authors.lastname: Contente
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Immacolata
authors.initials: I
authors.lastname: Serra
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Marta
authors.initials: M
authors.lastname: Brambilla
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Ivano
authors.initials: I
authors.lastname: Eberini
authors.affiliation: Department of Pharmacological and Biomolecular Sciences (DiSFeB), University of Milan, Via Balzaretti 9, 20133, Milano, Italy.
authors.forename: Elisabetta
authors.initials: E
authors.lastname: Gianazza
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Valerio
authors.initials: V
authors.lastname: De Vitis
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy.
authors.forename: Francesco
authors.initials: F
authors.lastname: Molinari
authors.affiliation: Department of Pharmacological and Biomolecular Sciences (DiSFeB), University of Milan, Via Balzaretti 9, 20133, Milano, Italy.
authors.forename: Paolo
authors.initials: P
authors.lastname: Zambelli
authors.affiliation: Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Mangiagalli 25, 20133, Milan, Italy. diego.romano@unimi.it.
authors.forename: Diego
authors.initials: D
authors.lastname: Romano
mesh_terms: D000429:Alcohol Oxidoreductases / Q000235:genetics* / Q000378:metabolism*; D003001:Cloning, Molecular; D003067:Coenzymes / Q000378:metabolism; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D015870:Gene Expression; D006841:Hydrocarbons, Aromatic / Q000378:metabolism*; D007659:Ketones / Q000378:metabolism*; D008958:Models, Molecular; D009249:NADP / Q000378:metabolism; D010843:Pichia / Q000201:enzymology* / Q000235:genetics*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D003067:Coenzymes; D006841:Hydrocarbons, Aromatic; D007659:Ketones; D009249:NADP; D000429:Alcohol Oxidoreductases; C446000:benzil reductase
keywords: Biocatalysis; Carbonyl reductase; Enantioselective reduction; Ketoreductase; Pichia glucozyma; Stereoselective