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KMID : 1094720120170050952
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Biotechnology and Bioprocess Engineering
2012 Volume.17 No. 5 p.952 ~ p.958
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Improved enantioselective hydrolysis of racemic ethyl-2,2-dimethylcyclopropanecarboxylate catalyzed by modified Novozyme 435
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Liang Fa-Yong
Huang Jin
He Jun-Yao
Wang Pu
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Abstract
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S-(+)-2,2-dimethylcyclopropanecarboxylic acid (S-(+)-DMCPA) is a key chiral intermediate for the synthesis of Cilastatin. The enzymatic preparation of S-(+)-DMCPA has attracted much attention. In order to improve the activity and stability of Novozyme 435 for enzymatic preparation of S-(+)-DMCPA from 2,2-dimethylcyclopropane carboxylate (DMCPE), the glutaraldehyde modification for Novozyme 435 was investigated and the glutaraldehydemodified Novozyme 435 was used as biocatalyst for the synthesis of S-(+)-DMCPA. The results showed that the modified Novozyme 435 had a better reusing merit than unmodified enzyme. The maximum specific activity was obtained by modification Novozyme 435 with 1.5% glutaraldehyde solution under the conditions of shaking at 200 rpm and 30°C for 45 min. The optimal enzymatic hydrolysis conditions for glutaraldehyde-modified Novozyme 435 were also confirmed. The optimized hydrolytic reaction mixture contained 10 mL potassium phosphate buffer (1.0 mol/L, pH 7.6), 90 mg of DMCPE and 160 mg of glutaraldehyde-modified enzyme, and the reaction was performed at 30oC and 200 rpm for 52 h. The reusing efficiency of modified Novozyme 435 was further evaluated. Under the optimal conditions, the modified enzyme remained 76.0% of its original yield after 10 times reuse, but the optical purity of the product kept intact; whereas the yield of unmodified enzyme reduced to 20.8% of its initial value and the ee value of product decreased a lot to 90.7% after 7 times recycle. These results showed that the modified Novozyme 435 was more cost-effective for the preparation of S-(+)-DMCPA in industrial application.
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KEYWORD
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ethyl-2,2-dimethylcyclopropanecarboxylate, glutaraldehyde, Novozyme 435, S-(+)-2,2-dimethylcyclopropanecarboxylic acid, modification
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