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( R )- p -chlorophenyl-1,2-ethanediol ( p CPED) is an important intermediate for the synthesis of ( R )-eliprodil that is widely applied in the treatment of ischemic stroke. To prepare ( R )- p CPED with high enantiomeric excess ( ee  p ) and yield via the enantioconvergent hydrolysis of racemic styrene oxide ( rac-p CSO) at high concentration, the bi-enzymatic catalysis was designed and investigated by a pair of epoxide hydrolases, a mutant ( Pv EH1 Z4X4-59 ) of  Phaseolus vulgaris  EH1 and a mutant ( Rp EH F361V ) of  Rhodotorula paludigena Rp EH .  Firstly, the maximum allowable concentration of  rac - p CSO was confirmed. Subsequently, the addition mode and the weight ratio of two  Escherichia coli  cells were optimized. Finally, under the optimized reaction conditions—the cell weight ratio 20:1 of  E. coli / pveh 1 z4x4-59  to  E. coli/rpeh  F361V , a simultaneous addition mode, and reaction temperature at 25°C—300 mM  rac-p CSO in the 100 ml 4% (v/v) Tween-20/phosphate buffer system (100 mM, pH 7.0) was completely hydrolyzed within 5 h, affording ( R )- p CPED with 87.8%  ee  p , 93.4% yield, and 8.63 g/L/h space–time yield (STY). This work would be an efficient technical strategy for the preparation of chiral vicinal diols at industrial scale.

Gram-Scale Synthesis of (R)-P-Chlorophenyl-1,2-Ethanediol at High Concentration by a Pair of Epoxide Hydrolases