Enantiopure epoxides and diols play an important role in pharmaceutical production. Mung bean epoxide hydrolase was found to be more active and enantioselective in catalyzing asymmetric hydrolysis of styrene oxide to (R)-1-phenyl-1,2ethanediol than other biocatalysts examined. Also, the faster enzymatic reaction effectively reduced the negative effect of the non-enzymatic hydrolysis of styrene oxide in aqueous phase, thus resulting in a remarkably enhanced yield and product e.e.. The optimal substrate concentration, buffer pH, reaction temperature and shaking rate for the reaction were 5 mM, 6.5, 35 oC and 220 r/min, respectively, under which the maximum yield and product e.e. reached 47.6% and 92.6%, being much higher than those using Solanum tuberosum epoxide hydrolase. Obviously, low substrate concentration and spontaneous hydrolysis of substrate in aqueous phase limits the application of the biocatalytic process. Our preliminary study demonstrates that ionic liquid-based systems might be good solution to this problem.

Asymmetric hydrolysis of racemic styrene oxide to (<i>R</i>)-1-phenyl-1,2-ethanediol catalyzed by Mung bean epoxide hydrolase

242nd National Meeting (2011)

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Asymmetric hydrolysis of racemic styrene oxide to (R)-1-phenyl-1,2-ethanediol catalyzed by Mung bean epoxide hydrolase