Preparation of S-(+)-ketoprofen by coupling the enantioselective hydrolysis of ketoprofen methyl ester with the photo-oxidation of methanol

Author: Zhu Shengdong   Wu Yuanxin   Yu Ziniu   Wang Cunwen   Yu Faquan   Ding Yigang   Jin Shiwei  

Publisher: Informa Healthcare

ISSN: 1024-2422

Source: Biocatalysis and Biotransformation, Vol.24, Iss.4, 2006-07, pp. : 306-310

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Abstract

A novel method for preparation of S-(+)-ketoprofen is presented involving coupling enantioselective hydrolysis of ketoprofen methyl ester catalyzed by a surfactant-coated-lipase with the photo-oxidation of methanol in a water-saturated organic solvent. The effect of photocatalytic conversion of methanol into water and carbon dioxide on the hydrolysis of ketoprofen methyl ester and the stability of the enzyme was investigated. The photo-oxidation of methanol shifted the equilibrium of the hydrolysis toward the formation of ketoprofen, increasing the equilibrium conversion ratio and improving the enantioselectivity. Because the surfactant-coated lipase and ketoprofen methyl ester dissolved in the organic solvent and ketoprofen was absorbed on the TiO 2 photocatalyst particles, the separation procedures could be simplified and the stability of the enzyme was increased.

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