KMID : 1094720140190030442
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Biotechnology and Bioprocess Engineering 2014 Volume.19 No. 3 p.442 ~ p.448
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Stepwise and combinatorial optimization of enantioselectivity for the asymmetric hydrolysis of 1-(3¡¯,4¡¯-methylenedioxyphenyl)ethyl acetate under use of a cold-adapted Bacillus amyloliquefaciens esterase
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Liu Jia-Yan
Zheng Gao-Wei Imanaka Tadayuki Xu Jian-He
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Abstract
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Optically pure 1-(3¡¯,4¡¯-methylenedioxyphenyl) ethanol is a key chiral intermediate for the synthesis of Steganacin and Salmeterol. A para-nitrobenzyl esterase cloned from Bacillus amyloliquefaciens (BAE) was employed to hydrolyze 1-(3¡¯,4¡¯-methylenedioxyphenyl) ethyl ester for the production of (R)-1-(3¡¯,4¡¯-methylenedioxyphenyl)ethanol. Initially, a moderate enantioselectivity (E = 35) only was obtained at 30¡ÆC. Some reaction conditions such as reaction temperature and additive approach were investigated in order to improve the enantioselectivity of the BAEcatalyzed reaction.. As a result, the enantioselectivity was improved significantly to 140 under addition of Tween-80 and a decreasing reaction temperature to 0¡ÆC. The result was confirmed in a decagram-scale preparative bioresolution also. The optimized enzymatic hydrolysis conditions provide a more effective process for the (R)-1-(3¡¯,4¡¯-methylenedioxyphenyl) ethanol bioproduction.
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KEYWORD
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1-(3¡¯,4¡¯-methylenedioxyphenyl)ethanol, Tween-80, low temperature, Bacillus amyloliquefaciens, paranitrobenzyl esterase
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