High-performance liquid chromatographic separation of fluorescent esters of hepoxilin enantiomers on a chiral stationary phase.

Fluorescent anthryl (ADAM) derivatives of hepoxilins have been shown to possess good chromatographic properties affording good sensitivity for the high-performance liquid chromatographic analysis and detection of these compounds and related eicosanoids (12-hydroxyeicosatetraenoic acid) in biological samples. We report herein the separation of all possible stereoisomers of hepoxilins A3 and B3 as their methyl esters as well as their ADAM ester and acetate derivatives on a cellulose trisdimethyphenylcarbamate chiral stationary phase (Chiracel OD) in the normal-phase mode. This methodology is important to address the mechanistic route of biosynthesis of these products.