1.1.1.423 (-)-(1R,2S)-ephedrine + NAD+ - Arthrobacter sp. TS-15 (S)-2-methylamino-1-phenylpropan-1-one + NADH + H+ - ? 449073 1.1.1.423 (-)-(1R,2S)-ephedrine + NAD+ the enzyme acts on a broad range of different aryl-alkyl ketones, such as haloketones, ketoamines, diketones, and ketoesters. It accepts various types of aryl groups including phenyl-, pyridyl-, thienyl-, and furyl-rings, but the presence of an aromatic ring is essential for the activity. In addition, the presence of a functional group on the alkyl chain, such as an amine, a halogen, or a ketone, is also crucial. The enzyme exhibits a strict Prelog enantioselectivity. When acting on diketones, it catalyses the reduction of only the keto group closest to the ring, with no further reduction to the diol. (-)-(1R,2S)-ephedrine i.e. (1R,2S)-1-phenyl-1-hydroxy-2-methylaminopropane. (S)-2-methylamino-1-phenylpropan-1-one i.e. (S)-methcathinone Arthrobacter sp. TS-15 (S)-2-methylamino-1-phenylpropan-1-one + NADH + H+ - ? 449073 1.1.1.423 (-)-(1R,2S)-ephedrine + NAD+ the enzyme exhibits a strict enantioselectivity for the oxidation of (-)-(1R,2S)-ephedrine and (R,R)-(-)-pseudoephedrine Arthrobacter sp. TS-15 (S)-2-methylamino-1-phenylpropan-1-one + NADH + H+ - ? 449073 1.1.1.423 (4-chlorophenyl)-2-pyridinylmethanone + NAD+ specifc activity: 1.74 U/mg. Product: 70% (S) enantiomeric excess Arthrobacter sp. TS-15 (S)-(4-chlorophenyl)(pyridin-2-yl)methanol + NADH + H+ - ? 454745 1.1.1.423 (4-chlorophenyl)-2-pyridinylmethanone + NADH + H+ 2.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 70% enantiomeric excess Arthrobacter sp. TS-15 (R)-(4-chlorophenyl)(pyridin-2-yl)methanol + NAD+ - ? 449082 1.1.1.423 (R,R)-(-)-pseudoephedrine + NAD+ the enzyme exhibits a strict enantioselectivity for the oxidation of (-)-(1R,2S)-ephedrine and (R,R)-(-)-pseudoephedrine Arthrobacter sp. TS-15 ? + NADH + H+ - ? 454757 1.1.1.423 1,2-indandione + NAD+ specifc 50.05 U/mg Arthrobacter sp. TS-15 ? + NADH + H+ - ? 454776 1.1.1.423 1,2-indanedione + NADH + H+ 78.1% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 1-hydroxy-1,3-dihydro-2H-inden-2-one + NAD+ - ? 449133 1.1.1.423 1,2-naphthoquinone + NAD+ specifc activity: 13.89 U/mg Arthrobacter sp. TS-15 ? + NADH + H+ - ? 454777 1.1.1.423 1,2-naphthoquinone + NADH + H+ 21.7% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 1-hydroxynaphthalen-2(1H)-one + NAD+ - ? 449135 1.1.1.423 1-phenyl-1,2-propanedione + NAD+ specifc activity: 64.02 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (R)-phenylacetylcarbinol + NADH + H+ - ? 454805 1.1.1.423 1-phenyl-1,2-propanedione + NADH + H+ substrate with highest activity. Full conversion and enantiomeric excess of more than 99% Arthrobacter sp. TS-15 (R)-phenylacetylcarbinol + NAD+ - ? 449150 1.1.1.423 1-phenyl-1,3-butanedione + NAD+ specifc activity: 13.64 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 (4R)-4-hydroxy-4-phenylbutan-2-one + NADH + H+ - ? 454807 1.1.1.423 1-phenyl-1,3-butanedione + NADH + H+ 21.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 (4R)-4-hydroxy-4-phenylbutan-2-one + NAD+ - ? 449152 1.1.1.423 1-phenyl-1-propanone + NAD+ specifc activity: 1.55 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-1-phenylpropan-1-ol + NADH + H+ - ? 454808 1.1.1.423 1-phenyl-1-propanone + NADH + H+ 2.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-1-phenylpropan-1-ol + NAD+ - ? 449153 1.1.1.423 2,2'-dichlorobenzil + NAD+ specifc activity: 27.91 U/mg. Product: 94% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NADH + H+ - ? 454873 1.1.1.423 2,2'-dichlorobenzil + NADH + H+ 43.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 4% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(2-chlorophenyl)-2-hydroxyethan-1-one + NAD+ - ? 449191 1.1.1.423 2,2'-furil + NAD+ specifc activity: 19.95 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-di(furan-2-yl)-2-hydroxyethan + NADH + H+ - ? 454875 1.1.1.423 2,2'-furil + NADH + H+ 20% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-di(furan-2-yl)-2-hydroxyethan-1-one + NAD+ - ? 449193 1.1.1.423 2,2'-thenil + NAD+ specifc activity: 46.77 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NADH + H+ - ? 454877 1.1.1.423 2,2'-thenil + NADH + H+ 46.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-di(thiophen-2-yl)ethan-1-one + NAD+ - ? 449194 1.1.1.423 2-aminoacetophenone + NAD+ specifc activity: 25.79 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-amino-1-phenylethan-1-ol + NADH + H+ - ? 454896 1.1.1.423 2-aminoacetophenone + NADH + H+ 40.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-amino-1-phenylethan-1-ol + NAD+ - ? 449200 1.1.1.423 2-bromo-1-(3-chlorophenyl)-1-propanone + NAD+ specifc activity: 5.1 U/mg Arthrobacter sp. TS-15 (R,S)-2-bromo-1-(3-chlorophenyl)propan-1-ol + NADH + H+ - ? 454899 1.1.1.423 2-bromo-1-(3-chlorophenyl)-1-propanone + NADH + H+ 7.9% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 2-bromo-1-(3-chlorophenyl)propan-1-ol + NAD+ - ? 449252 1.1.1.423 2-bromoacetophenone + NAD+ specifc activity: 9.44 U/mg. Product: 85% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-bromo-1-phenylethan-1-ol + NADH + H+ - ? 454904 1.1.1.423 2-bromoacetophenone + NADH + H+ 14.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 85% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-bromo-1-phenylethan-1-ol + NAD+ - ? 449254 1.1.1.423 2-chloro-1-phenyl-1-propane + NAD+ specifc activity: 8.0 U/mg Arthrobacter sp. TS-15 (R,S)-2-chloro-1-phenylpropan-1-ol + NADH + H+ - ? 454907 1.1.1.423 2-chloro-1-phenyl-1-propanone + NADH + H+ 12.5% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 2-chloro-1-phenyl-1-propan-1-ol + NAD+ - ? 449255 1.1.1.423 2-chloroacetophenone + NAD+ specifc activity: 8.71 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-chloro-1-phenylethan-1-ol + NADH + H+ - ? 454910 1.1.1.423 2-chloroacetophenone + NADH + H+ 13.6% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 (1R)-2-chloro-1-phenylethan-1-ol + NAD+ - ? 449257 1.1.1.423 2-thenoylacetonitrile + NAD+ specifc activity: 6.87 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (3R)-3-hydroxy-3-(thiophen-2-yl)propanenitril + NADH + H+ - ? 454945 1.1.1.423 2-thenoylacetonitrile + NADH + H+ 6.87% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(thiophen-2-yl)acetonitrile + NAD+ - ? 449275 1.1.1.423 3-chloropropiophenone + NAD+ specifc activity: 4.45 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (1R)-3-chloro-1-phenylpropan-1-ol + NADH + H+ - ? 454998 1.1.1.423 3-chloropropiophenone + NADH + H+ 6.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (1R)-3-chloro-1-phenylpropan-1-ol + NAD+ - ? 449279 1.1.1.423 4,4'-difluorobenzil + NAD+ specifc activity: 48.2 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NADH + H+ - ? 455026 1.1.1.423 4,4'-difluorobenzil + NADH + H+ 75.3% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-fluorophenyl)-2-hydroxyethan-1-one + NAD+ - ? 449302 1.1.1.423 4,4'-dimethylbenzil + NAD+ specifc activity: 3.12 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-bis(4-methylphenyl)ethan-1-one + NADH + H+ - ? 455028 1.1.1.423 4,4'-dimethylbenzil + NADH + H+ 4.8% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-1,2-bis(4-methylphenyl)-2-hydroxyethan-1-one + NAD+ - ? 449303 1.1.1.423 4-chlorobenzil + NAD+ specifc activity: 6.5 U/mg. Product: 95% (R) enantiomeric excess Arthrobacter sp. TS-15 ? + NADH + H+ - ? 455033 1.1.1.423 4-chlorobenzil + NADH + H+ 10.2% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 58% enantiomeric excess Arthrobacter sp. TS-15 ? + NAD+ - ? 449316 1.1.1.423 benzil + NAD+ specifc activity: 47.06 U/mg. Product: 99% enantiomeric (R) excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-diphenylethan-1-one + NADH + H+ - ? 455378 1.1.1.423 benzil + NADH + H+ 73.5% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-2-hydroxy-1,2-diphenylethan-1-one + NAD+ ? ? 449634 1.1.1.423 ethyl 2-chlorobenzoylacetate + NAD+ specifc activity: 35.21 U/mg Arthrobacter sp. TS-15 ethyl (R,S)-2-chloro-3-hydroxy-3-phenylpropanoate + NADH + H+ - ? 455656 1.1.1.423 ethyl 2-chlorobenzoylacetate + NADH + H+ 54.9% of the activity as compared to 1-phenyl-1,2-propanedione Arthrobacter sp. TS-15 ethyl 2-chloro-3-hydroxy-3-phenylpropanoate + NAD+ - ? 449901 1.1.1.423 isatin + NAD+ specifc activity: 7.84 U/mg. Product: 52% (R) enantiomeric excess Arthrobacter sp. TS-15 ? + NADH + H+ - ? 455793 1.1.1.423 isatin + NADH + H+ 12.25% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 52% enantiomeric excess Arthrobacter sp. TS-15 (3R)-3-hydroxy-1,3-dihydro-2H-indol-2-one + NAD+ - ? 450086 1.1.1.423 methyl benzoylformate + NAD+ specifc activity: 46.56 U/mg. Product: 98% (R) enantiomeric excess Arthrobacter sp. TS-15 methyl (2R)-hydroxy(phenyl)acetate + NADH + H+ - ? 455999 1.1.1.423 methyl benzoylformate + NADH + H+ 72.7% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 98% enantiomeric excess Arthrobacter sp. TS-15 methyl (2S)-hydroxy(phenyl)acetate + NAD+ - ? 450284 1.1.1.423 additional information no activity on (S,N)-(+)-(pseudo)ephedrine or (R,N)-(-)-(pseudo)ephedrine Arthrobacter sp. TS-15 ? - - 89 1.1.1.423 phenyl-2-pyridinylmethanone + NAD+ specifc activity: 2.81 U/mg. Product: 24% (R) enantiomeric excess Arthrobacter sp. TS-15 (R)-phenyl(pyridin-2-yl)methanol + NADH + H+ - ? 456255 1.1.1.423 phenyl-2-pyridinylmethanone + NADH + H+ 4.4% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 24% enantiomeric excess Arthrobacter sp. TS-15 (R)-phenyl(pyridin-2-yl)methanol + NAD+ - ? 450458 1.1.1.423 phenylglyoxal + NAD+ specifc activity: 12.1 U/mg. Product: 99% (R) enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(phenyl)acetaldehyde + NADH + H+ - ? 456259 1.1.1.423 phenylglyoxal + NADH + H+ 18.9% of the activity as compared to 1-phenyl-1,2-propanedione. The (R)-enantiomer is formed with 99% enantiomeric excess Arthrobacter sp. TS-15 (2R)-hydroxy(phenyl)acetaldehyde + NAD+ - ? 450463