Production of S-(+)-2-phenylpropionic acid from (R,S)-2-phenylpropionitrile by the combination of nitrile hydratase and stereoselective amidase in Rhodococcus equi TG328.
A new soil isolate, tentatively identified as Rhodococcus equi TG328, was found to be effective in the production of S-(+)-2-phenylpropionic acid from (R,S)-2-phenylpropionitrile. The conversion is catalysed by two enzymes. First, a nitrile hydratase converts the (R,S)-nitrile to (R,S)-2-phenylpropionamide. Second, a stereoselective amidase converts the S-(+)-amide to S-(+)-2-phenylpropionic acid. Conditions for optimal enzyme production and accumulation of S-(+)-2-phenylpropionic acid by resting cells were studied. The reaction of resting cells for 30 h at 10 degrees C with (R,S)-2-phenylpropionitrile resulted in the production of 100 g of S-(+)-2-phenylpropionic acid per litre of reaction mixture. The enantiometric excess of the purified S-(+)-2-phenylpropionic acid was 99.4%. The amount of S-(+)-2-phenylpropionic acid accumulated was enhanced by lower reaction temperatures. In addition, unreacted R-(-)-2-phenylpropionamide with 99.0% enantiometric excess was isolated.
Gilligan
T
T
Department of Agricultural Chemistry, Kyoto University, Japan.
Yamada
H
H
Nagasawa
T
T
D000097:Acetonitriles / Q000378:metabolism*; D000581:Amidohydrolases / Q000378:metabolism*; D006836:Hydro-Lyases / Q000378:metabolism*; D010666:Phenylpropionates / Q000378:metabolism*; D016929:Rhodococcus equi / Q000737:chemistry / Q000201:enzymology* / Q000502:physiology; D013237:Stereoisomerism; D013379:Substrate Specificity; D013696:Temperature
D000097:Acetonitriles; D010666:Phenylpropionates; C083412:2-phenylpropionitrile; C013025:hydratropic acid; D000581:Amidohydrolases; C019665:amidase; D006836:Hydro-Lyases; C048831:nitrile hydratase