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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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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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Authors and Affiliations

  1. State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, 200-237, China

    Jia-Yan Liu, Gao-Wei Zheng, Tadayuki Imanaka & Jian-He Xu

  2. Department of Biotechnology, College of Life Sciences, Ritsumeikan University, Shiga, 525-8577, Japan

    Tadayuki Imanaka

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  1. Jia-Yan Liu
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  2. Gao-Wei Zheng
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  3. Tadayuki Imanaka
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  4. Jian-He Xu
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Correspondence to Gao-Wei Zheng or Jian-He Xu.

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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

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