Biosynthesis of (R)-1,2-phenylethanediol and (R)-4-chloro-1,2-phenylethanediol by using two recombinant cells expressing enantiocomplementary epoxide hydrolases

Enantioconvergent biosynthesis of (R)-phenyl-1,2-ethanediol and (R)-4-chlorophenyl-1,2-ethanediol using two types of recombinant Escherichia coli cells expressing epoxide hydrolase of Caulobacter crescentus (CcEH) and a triple-point mutated EH of Mugil cephalus was investigated. The CcEH gene in pET28b(+) was expressed at 15 °C, and the reaction conditions such as biocatalyst ratio, reaction temperature and detergent addition were optimized to give best enantiopurity and yield. When two recombinant E. coli cells were used in sequential mode, (R)-phenyl-1,2-ethandiol with 90% enantiopurity and 95% yield was obtained in batch reaction. From 100 mM racemic 4-chlorostyrene oxide, (R)-4-chlorophenyl-1,2-ethanediol with 92% enantiopurity and 71% yield could be obtained.