Abstract
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°C. 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°C. 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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Liu, JY., Zheng, GW., Imanaka, T. et al. 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. Biotechnol Bioproc E 19, 442–448 (2014). https://doi.org/10.1007/s12257-013-0559-y
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DOI: https://doi.org/10.1007/s12257-013-0559-y