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Determination of the regioselectivity during epoxide hydrolase oxirane ring opening: a new method from racemic epoxides

1998; Elsevier BV; Volume: 5; Issue: 1-4 Linguagem: Inglês

10.1016/s1381-1177(98)00037-x

1873-3158

Philippe Moussou, Alain Archelas, J. Baratti, Roland Furstoss,

Eicosanoids and Hypertension Pharmacology

We describe here a new method for the determination of the regioselectivity of the oxirane ring opening involved in the Epoxide Hydrolase (EH) catalysed hydrolysis of epoxides, simply by starting from the racemic epoxide as a substrate. This method also allows to simultaneously determine the E ratio according to Sih's equation, whose applicability in this context is discussed. This approach affords a complete characterization of the biocatalysed epoxide opening, where three different stereochemical behaviours may be distinguished.