| Autor: |
Zhe-Ming Wu, Jian-Yong Zheng, Yu-Guo Zheng, Ren-Chao Zheng, Ai-Peng Li |
| Rok vydání: |
2012 |
| Předmět: |
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| Zdroj: |
Tetrahedron: Asymmetry. 23:1517-1521 |
| ISSN: |
0957-4166 |
| DOI: |
10.1016/j.tetasy.2012.10.011 |
| Popis: |
( S )-3-Cyano-5-methylhexanoic acid ethyl ester is a valuable synthetic intermediate for pregabalin. Immobilized lipase PS from Pseudomonas cepacia was screened and shown to be the best biocatalyst for the enantioselective hydrolysis of 3-cyano-5-methylhexanoic acid ethyl ester, a racemic mixture involving a β-stereocenter. The optimum temperature and pH for the biocatalytic process were 35 °C and 6.0, respectively. Lipase PS IM exhibited a strong tolerance toward high substrate concentrations of up to 2.0 M (366 g/l). In the scaled-up biotransformation, ( S )-3-cyano-5-methylhexanoic acid ethyl ester was produced in 0.89 M (162.9 g/l), 99.2% ee , and 44.5% yield. These results indicated that lipase PS IM catalyzed the preparation of ( S )-3-cyano-5-methylhexanoic acid ethyl ester and could be used as an efficient route for the large-scale production of pregabalin. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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