Resolution of epoxyeicosatrienoate enantiomers by chiral phase chromatography.

A chromatographic method is described for the direct enantiomeric characterization of all four regioisomeric epoxyeicosatrienoic acid (EET) metabolites generated by the cytochrome P450 arachidonate epoxygenase pathway. Following esterification, the individual methyl or pentafluorobenzyl esters are resolved by chiral phase HPLC utilizing a Chiralcel OB or OD column. This methodology will find analytical and preparative applications for chiral epoxides since it is convenient and efficient and does not destroy the epoxide functionality.