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- Title
Enzymatic Synthesis of a Key Intermediate for Rosuvastatin by Nitrilase-Catalyzed Hydrolysis of Ethyl ( R)-4-Cyano-3-hydroxybutyate at High Substrate Concentration.
- Authors
Yao, Peiyuan; Li, Jianjiong; Yuan, Jing; Han, Chao; Liu, Xiangtao; Feng, Jinhui; Wu, Qiaqing; Zhu, Dunming
- Abstract
An enzymatic method for the synthesis of ethyl ( R)-3-hydroxyglutarate from ethyl ( R)-4-cyano-3-hydroxybutyate was developed by using free and immobilized recombinant Escherichia coli BL21(DE3)pLysS harboring a nitrilase gene from Arabidopsis thaliana (AtNIT2). The hydrolysis of ethyl ( R)-4-cyano-3-hydroxybutyate proceeded with the freely suspended cells of the biocatalyst under the optimized conditions of 1.5 mol L−1 (235.5 g L−1) substrate concentration and 6.0 wt % loading of wet cells at pH 8.0 and 25 °C, with 100 % conversion obtained in 4.5 h. Furthermore, immobilization of the whole cells enhanced their substrate tolerance, stability, and reusability. Under the optimized conditions (100 mmol L−1 tris(hydroxymethyl)aminomethane hydrochloride buffer, pH 8.0, 25 °C), the immobilized biocatalyst could be reused for up to 16 batches, with a biocatalyst productivity of 55.6 g gwet cells−1 and a space-time productivity of 625.5 g L−1 d−1. These results demonstrated that the immobilized whole cells might be used as a biocatalyst in the industrial production of ethyl ( R)-3-hydroxyglutarate, a key intermediate for the synthesis of rosuvastatin.
- Subjects
CATALYTIC hydrolysis; ROSUVASTATIN; INTERMEDIATES (Chemistry); ENCAPSULATION (Catalysis); NITRILASES; ORGANIC synthesis; BIOTRANSFORMATION (Metabolism)
- Publication
ChemCatChem, 2015, Vol 7, Issue 2, p271
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201402877