1.1.1.320 (S)-benzoin + NADP+ stereospecific asymmetric reduction of benzil to (S)-benzoin Bacillus cereus benzil + NADPH + H+ - r 417829 1.1.1.320 (S)-benzoin + NADP+ stereospecific asymmetric reduction of benzil to (S)-benzoin, recombinant Bacillus cereus benzil reductase produces optically pure (S)-benzoin with NADPH in vitro Bacillus cereus benzil + NADPH + H+ - r 417829 1.1.1.320 (S)-benzoin + NADP+ stereospecific asymmetric reduction of benzil to (S)-benzoin Bacillus cereus Tim-r01 benzil + NADPH + H+ - r 417829 1.1.1.320 1-(2-fluorophenyl)ethanone + NADPH + H+ 76% of the rate with 1-(4-nitrophenyl)ethanone, 97% yield, 94% enantiomeric excess Ogataea glucozyma (1S)-1-(2-fluorophenyl)ethanol + NADP+ - ? 438616 1.1.1.320 1-(2-nitrophenyl)ethanone + NADPH + H+ 53% of the rate with 1-(4-nitrophenyl)ethanone, 78% yield, 98% enantiomeric excess Ogataea glucozyma (1S)-1-(2-nitrophenyl)ethanol + NADP+ - ? 438617 1.1.1.320 1-(3-fluorophenyl)ethanone + NADPH + H+ 61% of the rate with 1-(4-nitrophenyl)ethanone, 85% yield, 98% enantiomeric excess Ogataea glucozyma (1S)-1-(3-fluorophenyl)ethanol + NADP+ - ? 438618 1.1.1.320 1-(4-fluoro-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+ - Bacillus cereus ? + NADP+ - ? 418196 1.1.1.320 1-(4-methyl-phenyl)-2-phenyl-ethane-1,2-dione + NADPH + H+ - Bacillus cereus ? + NADP+ - ? 418197 1.1.1.320 1-(4-nitrophenyl)ethanone + NADPH + H+ 100% yield, 98% enantiomeric excess Ogataea glucozyma (1S)-1-(4-nitrophenyl)ethanol + NADP+ - ? 438619 1.1.1.320 1-(furan-2-yl)ethanone + NADPH + H+ - Ogataea glucozyma (1S)-1-(furan-2-yl)ethanol + NADP+ 48% of the activity with benzil, 95% yield, 98% enantiomeric excess ? 438620 1.1.1.320 1-(pyridin-3-yl)ethanone + NADPH + H+ - Ogataea glucozyma (S)-(1-pyridin-3yl)ethanol + NADP+ 58% of the activity with benzil, 95% yield, 98% enantiomeric excess ? 438621 1.1.1.320 1-(pyridin-3-yl)propan-1-one + NADPH + H+ - Ogataea glucozyma (S)-1-(pyridin-3-yl)propanol + NADP+ 60% of the activity with benzil, 95% yield, 98% enantiomeric excess ? 438622 1.1.1.320 1-(thiophen-2-yl)ethanone + NADPH + H+ - Ogataea glucozyma (1S)-1-(thiophen-2-yl)ethanol + NADP+ 51% of the activity with benzil, 95% yield, 98% enantiomeric excess ? 438623 1.1.1.320 1-phenyl-1,2-propanedione + NADPH + H+ - Bacillus cereus ? + NADP+ - ? 418202 1.1.1.320 2-acetylbenzonitrile + NADPH + H+ 82% of the rate with 1-(4-nitrophenyl)ethanone, 98% yield, 98% enantiomeric excess Ogataea glucozyma 2-[(1S)-1-hydroxyethyl]benzonitrile + NADP+ - ? 438708 1.1.1.320 2-hydroxy-1-phenyl-1-propanone + NADP+ - Bacillus cereus 1-phenylpropane-1,2-dione + NADPH + H+ - ? 422403 1.1.1.320 3-oxo-3-phenylpropanenitrile + NADPH + H+ - Ogataea glucozyma (3S)-3-hydroxy-3-phenylpropanenitrile + NADP+ 55% of the activity with benzil, 95% yield, 95% enantiomeric excess ? 438807 1.1.1.320 4-acetylbenzonitrile + NADPH + H+ 68% of the rate with 1-(4-nitrophenyl)ethanone, 70% yield, 97% enantiomeric excess Ogataea glucozyma 4-[(1S)-1-hydroxyethyl]benzonitrile + NADP+ - ? 438824 1.1.1.320 benzil + NADPH + H+ - Ogataea glucozyma (S)-benzoin + NADP+ - r 439246 1.1.1.320 benzil + NADPH + H+ - Ogataea glucozyma (S)-benzoin + NADP+ 98% enantiomeric excess ? 439246 1.1.1.320 benzophenone + NADPH + H+ - Ogataea glucozyma diphenylmethanol + NADP+ 66% yield ? 439247 1.1.1.320 ethyl 2-oxo-2-phenylacetate + NADPH + H+ - Ogataea glucozyma ethyl (2S)-hydroxy(phenyl)acetate + NADP+ 115% yield, 40% enantiomeric excess ? 439520 1.1.1.320 additional information the enzyme is also active with 1,4-naphthoquinone, dichlone, and 4-phenylbenzaldehyde, substrate specificity, overview. 1-acenaphthenol is oxidized, although the kcat/Km ratio is low. No activity with progesterone, daunorubicin, and menaquinone. No or poor activity with benzyl phenyl ketone, benzophenone, dibenzoylmethane, chalcone, 1-phenyl-1,3-butanedione, diacetyl, 3,4-hexanedione, and acetophenone Bacillus cereus ? - ? 89 1.1.1.320 additional information for the enantioselective reduction of mono-substituted acetophenones, reaction rates of meta- and para-derivatives are consistent with the electronic effects described by delta-Hammett coefficients. Enantioselectivity is determined by an opposite orientation of the substrate in the binding pocket. Reduction of ortho-derivatives occurs only with substrates bearing substituents with low steric impact, and reactivity is controlled by stereoelectronic features Ogataea glucozyma ? - ? 89 1.1.1.320 additional information the enzyme prefers space-demanding substrates, which are often converted with high stereoselectivity Ogataea glucozyma ? - ? 89 1.1.1.320 additional information the enzyme is preferentiallly active on aromatic 1,2-diketones. It catalyzes the stereoselective monoreduction and desymmerization of bulky dicarbonyls. Mechanism and in silico prediction of substrates reactivity, overview Ogataea glucozyma ? - - 89 1.1.1.320 sec-phenethyl alcohol + NADP+ - Bacillus cereus 1-phenylethanone + NADPH + H+ - ? 419067