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Literature summary for 3.5.5.1 extracted from

  • Ankati, H.; Zhu, D.; Yang, Y.; Biehl, E.R.; Hua, L.
    Asymmetric synthesis of both antipodes of beta-hydroxy nitriles and beta-hydroxy carboxylic acids via enzymatic reduction or sequential reduction/hydrolysis (2009), J. Org. Chem., 74, 1658-1662.
    View publication on PubMed
Search for more literature for 3.5.5.1

Application

Application Comment Organism
synthesis synthesis of beta-hydroxy carboxylic acids with high yield and optical purity by reudction of aromatic beta-ketonitriles with recombinant carbonyl reductase and nitrilase-catalyzed hydrolysis Bradyrhizobium japonicum

Organism

Organism UniProt Comment Textmining
Bradyrhizobium japonicum
-
 strain USDA110
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Bradyrhizobium japonicum USDA 110
-
 strain USDA110
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
(3S)-3-(2,4-difluorophenyl)-3-hydroxypropanenitrile + H2O 91% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(2,4-difluorophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(2,4-difluorophenyl)-3-hydroxypropanenitrile + H2O 91% yield, 99% enantiomeric excess Bradyrhizobium japonicum USDA 110 (3S)-3-(2,4-difluorophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(3-methoxyphenyl)-3-hydroxypropanenitrile + H2O 88% yield, 95% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(3-methoxyphenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(3-methoxyphenyl)-3-hydroxypropanenitrile + H2O 88% yield, 95% enantiomeric excess Bradyrhizobium japonicum USDA 110 (3S)-3-(3-methoxyphenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(3-nitrophenyl)-3-hydroxypropanenitrile + H2O 88% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(3-nitrophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(3-nitrophenyl)-3-hydroxypropanenitrile + H2O 88% yield, 99% enantiomeric excess Bradyrhizobium japonicum USDA 110 (3S)-3-(3-nitrophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-bromophenyl)-3-hydroxypropanenitrile + H2O 89% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-bromophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-bromophenyl)-3-hydroxypropanenitrile + H2O 89% yield, 99% enantiomeric excess Bradyrhizobium japonicum USDA 110 (3S)-3-(4-bromophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-chlorophenyl)-3-hydroxypropanenitrile + H2O 92% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-chlorophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-chlorophenyl)-3-hydroxypropanenitrile + H2O 92% yield, 99% enantiomeric excess Bradyrhizobium japonicum USDA 110 (3S)-3-(4-chlorophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-cyanophenyl)-3-hydroxypropanenitrile + H2O 92% yield, 95% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-cyanophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-fluorophenyl)-3-hydroxypropanenitrile + H2O 93% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-fluorophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-methoxyphenyl)-3-hydroxypropanenitrile + H2O 91% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-methoxyphenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-methylphenyl)-3-hydroxypropanenitrile + H2O 91% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-methylphenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-(4-nitrophenyl)-3-hydroxypropanenitrile + H2O 87% yield, 97% enantiomeric excess Bradyrhizobium japonicum (3S)-3-(4-nitrophenyl)-3-hydroxypropanoic acid + NH3
-
 ?
(3S)-3-hydroxy-3-phenylpropanenitrile + H2O 90% yield, 99% enantiomeric excess Bradyrhizobium japonicum (3S)-3-hydroxy-3-phenylpropanoic acid + NH3
-
 ?