The Isolation and Characterisation of a Carbocyclic Epoxide-Degrading Corynebacterium sp

A two-phase aqueous/organic isolation system was developed for the isolation of epoxide-degrading bacteria. The potential of this system, for the isolation of cyclohexene oxide-degrading bacteria, was assessed by comparison to an analogous system lacking co-solvent. Using the biphasic isolation strategy, an epoxide-degrading Corynebacterium sp. designated C12, was isolated and was shown to grow on cyclohexene oxide as sole source of carbon and energy. Epoxide degradation appeared to proceed via a diol intermediate implicating the involvement of an epoxide hydrolase. The epoxide hydrolase of Corynebacterium sp. C12 was shown to have activity towards a range of terminal, sub-terminal and cyclic substrates. The enantioselectivity of the hydrolysis reaction was largely dependent on the nature of the substrate. In a series of biotransformations allowed to proceed to 50% substrate conversion, the remaining epoxide ranged from low (5% ee) to moderate (60% ee) optical purity.