Biocatalytic desymmetric hydrolysis of 3-(4-chlorophenyl)-glutaronitrile to the key precursor of optically pure baclofen / 生物工程学报
Chinese Journal of Biotechnology
; (12): 31-40, 2013.
Article
in Chinese
| WPRIM (Western Pacific)
| ID: wpr-233272
Responsible library:
WPRO
ABSTRACT
We produced (S)-4-cyano-3-(4-chlorophenyl)-butyrate by highly stereoselective biocatalyst in this study. A nitrilase-producing strain, named Gibberella intermedia WX12, was isolated by 3-(4-chlorophenyl)-glutaronitrile as substrate in the screening with phenol-sodium hypochlorite method. The fermentation conditions and catalytic properties of this strain were investigated. The preferred carbon and nitrogen sources for nitrilase production were lactose (30 g/L) and peptone (20 g/L). After being cultivated for 96 h, the cells were collected for use in biotransformation. The hydrolysis of 3-(4-chlorophenyl)-glutaronitrile was performed at 30 degrees C in phosphate buffer (pH 8.0, 50 mmol/L) for 24 h to give (S)-4-cyano-3-(4-chlorophenyl)-butyric acid with 90% yield and > 99% of ee, which can be used for the synthesis of (R)- and (S)-baclofen. The configuration of product was determined by chemically converting it to baclofen and comparison with the authentic sample by chiral HPLC analysis.
Full text:
Available
Database:
WPRIM (Western Pacific)
Main subject:
Baclofen
/
Prodrugs
/
Chemistry
/
Chlorophenols
/
Biocatalysis
/
Gibberella
/
Aminohydrolases
/
Hydrolysis
/
Metabolism
/
Nitriles
Language:
Chinese
Journal:
Chinese Journal of Biotechnology
Year:
2013
Document type:
Article