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
en Zh
| WPRIM
| ID: wpr-233272
Biblioteca responsable:
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.
Texto completo:
1
Base de datos:
WPRIM
Asunto principal:
Baclofeno
/
Profármacos
/
Química
/
Clorofenoles
/
Biocatálisis
/
Gibberella
/
Aminohidrolasas
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Hidrólisis
/
Metabolismo
/
Nitrilos
Idioma:
Zh
Revista:
Chinese Journal of Biotechnology
Año:
2013
Tipo del documento:
Article