Enantioselective lipase-catalyzed kinetic resolution of N-(2-ethyl-6-methylphenyl)alanine |
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Authors: | Liangyu Zheng Suoqin Zhang Yan Feng Shugui Cao Jisheng Ma Lifang Zhao Gui Gao |
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Affiliation: | aKey Laboratory for Molecular Enzymology and Engineering of Ministry of Education bCollege of Chemistry, Jilin University, Changchun 130023, PR China |
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Abstract: | The enzyme (BSL2), a highly active lipase expressed from newly constructed strain of Bacillus subtilis BSL2, is used in the kinetic resolution of N-(2-ethyl-6-methylphenyl)alanine from the corresponding racemic methyl ester. Reaction conditions are optimized to enhance the enantioselectivity. The effects of various racemic alkyl esters, substrate concentration, operating temperature, pH of the aqueous medium and organic solvents on activity and enantioselectivity of BSL2 for kinetic resolution are also studied. A high enantiomeric ratio (E = 60.7) is reached in diisopropyl ether/water (10%, v/v) and the enantioselectivity is about 22-fold higher than that in pure buffered aqueous solution. The results show that the reaction medium greatly influences BSL2 reaction and its enantioselectivity in the hydrolysis of racemic methyl ester. |
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Keywords: | Bacillus subtilis BSL2 Kinetic resolution Hydrolysis (S)-(–)-N-(2-ethyl-6-methylphenyl)alanine |
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