Epoxide (EC 3.3.2.3) catalyzes the S_N²-hydrolysis of a variety of epoxides to trans-1,2-diols. An aspartic acid is essential in the active site, which usually functions as an intermediate nucleophile (see Reaction Scheme and Examples). They do not require cofactors and often show high regio- and enantioselectivity (see References).

Reaction Scheme and Examples:

Selected References:

1. van Loo, B.; Kingma, J.; Arand, M.; Wubbolts, M. G.; Janssen, D. B.   “Diversity and biocatalytic potential of  epoxide  hydrolases identified by genome analysis”,  Applied and Environmental Microbiology, 2006,  72,  2905-2917.

2. Smit, M. S.; Labuschagne, M.   “Diversity of  epoxide   hydrolase  biocatalysts”,    Current Organic Chemistry, 2006,  10,  1145-1161.

3. Xu, W.; Xu, J.-H.; Pan, J.; Gu, Q.; Wu, X.-Y.   “Enantioconvergent Hydrolysis of Styrene Epoxides by Newly Discovered Epoxide Hydrolases in Mung Bean”,   Organic Letters, 2006, 8, 1737-1740.