Table 1.
Substrates converted by PEDH
| No | Substrate | Product | S [%] | R [%] | %ee |
|---|---|---|---|---|---|
| Aromatic ketones | |||||
| 1 | acetophenone | 1-phenylethanol | 100 | 0 | 100 |
| 2 | propiophenone | 1-phenylpropan-1-ol | 100 | 0 | 100 |
| 3 | 2-chloroacetophenone | 2-chloro-1-phenylethanol | 0 | 100 | 100 |
| 4 | 4′-ethylacetophenone | 1-(4-ethylphenyl)ethanol | 100 | 0 | 100 |
| 5 | 4′-acetyl acetophenone | 1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol | 100 | 0 | 100 |
| 6 | (S)-1-[4-(1-hydroxyethyl)phenyl]-methylketone | 1-(4-(1-hydroxy-ethyl)-phenyl)-ethanol | 100 | 0 | 100 |
| 7 | 4′-acetylbiphenyl | 1-(biphenyl-4-yl)ethanol | 100 | 0 | 100 |
| 8 | 4′-acetylphenyl methanesulfonate | 4-(1-hydroxyethyl)phenyl methanesulfonate | 100 | 0 | 100 |
| 9 | 4′-nitroacetophenone | 1-(4-nitrophenyl)ethanol | 100 | 0 | 100 |
| 10 | 4′-fluoroacetophenone | 1-(4-fluorophenyl)ethanol | 100 | 0 | 100 |
| 11 | 3′-hydroxyacetophenone | 3-[(1)-1-hydroxyethyl]phenol | 100 | 0 | 100 |
| 12 | 3′-methylacetophenone | 1-(3-methylphenyl)ethanol | 100 | 0 | 100 |
| 13 | 1-indanone | 1-indanol | 100 | 0 | 100 |
| 14 | 1-(furan-2-yl)methylketone | 1-(furan-2-yl)ethanol | 100 | 0 | 100 |
| 15 | 3-acetylpyridine | 1-(pyridin-3-yl)ethanol | 100 | 0 | 100 |
| 16 | 2-acetylthiophene | 1-(thiophen-2-yl)ethanol | 100 | 0 | 100 |
| 17 | 2-acetylpyridine | 1-(pyridin-2-yl)ethanol | 100 | 0 | 100 |
| 18 | 4-acetylpyridine | 1-(pyridin-4-yl)ethanol | 100 | 0 | 100 |
| 19 | 1-tetralone | 1,2,3,4-tetrahydronaphthalen-1-ol | 100 | 0 | 100 |
| 20 | 4′-methoxyacetophenone | 1-(4-methoxyphenyl)ethanol | 100 | 0 | 100 |
| 21 | 4′-aminoacetophenone | 1-(4-aminophenyl)ethanol | 50 | 50 | 0 |
| 22 | 4′-hydroxyacetophenone | 4-(1-hydroxyethyl)phenol | 95 | 5 | 90 |
| 23 | 2′-hydroxyacetophenone | 2-(1-hydroxyethyl)phenol | 100 | 0 | 100 |
| 24 | (S)-3-phenyl-1-indanone | (S)-3-phenyl-1-indanol | 100 | ||
| 25 | 6-hydroxy-1-indanone | 2,3-dihydro-1H-indene-1,6-diol | 100 | ||
| 26 | 2′-fluoroacetophenone | 1-(2-fluorophenyl)ethanol | 100 | ||
| 27 | 2,2-dichloroacetophenone | 2,2-dichloro-1-phenylethanol | 100 | ||
| 28 | 2,4′-dichloroacetophenone | 2-chloro-1-(4-chloro-phenyl)-ethanol | 100 | ||
| 29 | 2,2,2-trifluoroacetophenone | 1-phenyl-2,2,2-trifluoroethan-1-ol | 100 | ||
| 30 | 2,2-difluoroacetophenone | 1-phenyl-2,2-trifluoroethan-1-ol | 100 | ||
| 31 | 2-fluoroacetophenone | 2-fluoro-1-phenylethan-1-ol | 100 | ||
| 32 | 3′-aminoacetophenone | 1-(3-aminophenyl)ethanol | 100 | ||
| 33 | 4′-chloroacetophenone | 1-(4-chlorophenyl)ethanol | 100 | ||
| 34 | 4′-bromoacetophenone | 1-(4-bromophenyl)ethanol | 100 | ||
| 35 | 4-acetylbenzonitrile | 4-(1-hydroxyethyl)benzonitrile | 100 | ||
| 36 | 2-cyanoacetophenone | 3-hydroxy-3-phenylpropanenitrile | 100 | ||
| 37 | 3′-chloroacetophenone | 1-(3-chlorophenyl)ethanol | 100 | ||
| 38 | 3′-methoxyacetophenone | 1-(3-methoxyphenyl)ethanol | 100 | ||
| 39 | 3-coumaranone | 2,3-dihydro-1-benzofuran-3-ol | 100 | ||
| 40 | 3'-fluoroacetophenone | 1-(3-fluorophenyl)ethanol | 100 | ||
| 41 | 3'-bromoacetophenone | 1-(3-bromophenyl)ethanol | 100 | ||
| 42 | (R)-3-phenyl-1-indanol | (R)-3-phenyl-1-indanol | 100 | ||
| β-keto esters | |||||
| 43 | methyl 4-fluorobenzoylacetate | methyl 3-(4-fluorophenyl)-3-hydroxypropanoate | 100 | 0 | 100 |
| 44 | methyl (4-chlorobenzoyl)acetate | methyl 3-(4-chlorophenyl)-3-hydroxypropanoate | 100 | 0 | 100 |
| 45 | methyl 4-bromobenzoylacetate | methyl 3-(4-bromophenyl)-3-hydroxypropanoate | 100 | 0 | 100 |
| 46 | 3-(4-methoxy-phenyl)-3-oxo-propionic acid methyl ester | methyl 3-hydroxy-3-(4-methoxyphenyl)propanoate | 100 | 0 | 100 |
| 47 | 3-(3-bromo-phenyl)-3-oxo-propionic acid methyl ester | methyl 3-(3-bromophenyl)-3-hydroxypropanoate | 100 | ||
| 48 | 3-(3-methoxyphenyl)-3-oxo-propionic acid methylester | methyl 3-hydroxy-3-(3-methoxyphenyl)propanoate | 100 | ||
| 49 | 3-(3-chloro-phenyl)-3-oxo-propionic acid methyl ester | methyl 3-(3-chlorophenyl)-3-hydroxypropanoate | 100 | ||
| 50 | 3-(3-fluoro-phenyl)-3-oxo-propionic acid methyl ester | methyl 3-(3-fluorophenyl)-3-hydroxypropanoate | 100 | ||
| 51 | methyl 3-(4-methylphenyl)-3-oxopropanoate | methyl 3-hydroxy-3-(4-methylphenyl)propanoate | 100 | ||
| 52 | methyl 3-(4-ethylphenyl)-3-oxopropanoate | methyl 3-(4-ethylphenyl)-3-hydroxypropanoate | 100 | ||
| 53 | methyl 3-oxo-3-phenylpropanoate | methyl 3-hydroxy-3-phenylpropanoate | 100 | ||
S/R [%] amount of isomers identified based on chiral standards and absolute configurations, %ee enantiomeric excess identified based of racemic standards or Chiralcel OB-H applications: 1-(3-chlorophenyl)ethanol (Kodama et al. 2012), 1-(3-methoxyphenyl)ethanol (Itoh et al. 2002), 2-chloro-1-(4-chloro-phenyl)-ethanol (Itoh et al. 2002), 1-(4-chlorophenyl)ethanol (Szaleniec 2012), 1-(3-fluorophenyl)ethanol (Banoglu and Duffel 1997), 1-(pyridin-3-yl)ethanol, and 1-(pyridin-4-yl)ethanol (Machado et al. 2009). Tests conducted with benzophenone (diphenylmethanone) showed no enzymatic activity