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Molecules 2014, 19(6), 8067-8079; doi:10.3390/molecules19068067

Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain

College of Biological and Environmental Engineering, Zhejiang University of Technology, Hangzhou 310014, China
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Received: 3 May 2014 / Revised: 6 June 2014 / Accepted: 11 June 2014 / Published: 16 June 2014
(This article belongs to the Section Natural Products)
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Abstract

A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol’s side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e.S > 95%). View Full-Text
Keywords: ethyl 3-phenylglycidate; Galactomyces geotrichum; epoxide hydrolase; synthesis; bioresolution ethyl 3-phenylglycidate; Galactomyces geotrichum; epoxide hydrolase; synthesis; bioresolution
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MDPI and ACS Style

Wei, C.; Ling, J.; Shen, H.; Zhu, Q. Bioresolution Production of (2R,3S)-Ethyl-3-phenylglycidate for Chemoenzymatic Synthesis of the Taxol C-13 Side Chain by Galactomyces geotrichum ZJUTZQ200, a New Epoxide-Hydrolase-Producing Strain. Molecules 2014, 19, 8067-8079.

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