Bioproduction of (2R,3R)-3-Phenylglycidiol: A Key Chiral Synthon for Drugs Bearing 3-Phenylpropane Using a Newly-Isolated Strain of Aspergillus fumigatus ZJUTZQ160
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We report a novel and effective biosynthesis of (2R,3R)-3-phenylglycidiol using Aspergillus fumigatus ZJUTZQ160. After optimization of the biotransformation conditions, (2R,3R)-PG was obtained with good enantioselectivity (e.e. s > 99.9 %, E > 58.6). Gram-scale preparation of (2R,3R)- 3-phenylglycidiol was successfully performed within 16 h (yield = 35.6 %, e.e.s > 99.9 %), indicating that A. fumigatus ZJUTZQ160 is a valuable biocatalyst for the efficient preparation of optically active epoxides. The conversion of (2R,3R)- 3-phenylglycidiol to optically pure (2S,3S)-3-azido-3-phenyl-propane-1,2-diol was also successfully achieved with excellent yield (92 %) and e.e. s (>94 %) after the nucleophilic substitution reaction with sodium azide.
KeywordsChiral epoxides Epoxide hydrolase Epoxy cinnamyl alcohol Aspergillus fumigates Enantioselectivity
This work was supported by National Science Foundation of China (No. 21272212) and Zhejiang Natural Science Fund (No. LY12B02018).
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