Stereoselective esterification of halogen-containing carboxylic acids by lipase in organic solvent: effects of alcohol chain length |
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| Authors: | Shi-Hao Pan Takuo Kawamoto Toshiaki Fukui Kenji Sonomoto Atsuo Tanaka |
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| Affiliation: | (1) Laboratory of Industrial Biochemistry, Department of Industrial Chemistry, Faculty of Engineering, Kyoto University, Yoshida, Sakyo-ku, 606 Kyoto, Japan;(2) Present address: Shanghai Center of Biotechnology, Chinese Academy of Science, 319 Yoyang Road, Shanghai, The People's Republic of China |
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| Abstract: | Summary Optical resolution of racemic carboxylic acids containing a halogen atom was attempted with stereoselective esterificatiob by Celite-adsorbed hydrolases in organic solvents. As lipase OF 360 from Candida cylindracea was found to stereoselectively esterify 2-(4-chlorophenoxy)propanoic acid, the (R)-enantiomer (d-isomer) of which is an important herbicide, the effects of alcohol chain length on stereoselectivity as well as reaction rate were investigated. The results revealed that the alcohol chain length markedly affected the stereoselective esterification of 2-(4-chlorophenoxy)propanoic acid: longer-chain alcohols, such as tetradecanol, served as excellent substrates for optical resolution of the acid, although the reaction rate was moderate.Offprint requests to: A. Tanaka |
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