Direct enantiomeric resolution of cyclic alcohol derivatives of polycyclic aromatic hydrocarbons by chiral stationary phase high-performance liquid chromatography.

The enantiomers of some cyclic alcohol derivatives of phenanthrene, benz[a]anthracene, benzo[a]pyrene, cholanthrene, and 3-methylcholanthrene were resolved by high-performance liquid chromatography using a commercially available preparative column packed with an (R)-N-(3,5-dinitrobenzoyl)phenylglycine ionically bonded to gamma-aminopropylsilanized silica. Resolution of enantiomers was confirmed by ultraviolet-visible absorption, mass and circular dichroism spectral analyses. This method has been applied to the determination of optical purity of 1-hydroxycholanthrene and 1-hydroxy-3-methylcholanthrene formed in the metabolism of cholanthrene and 3-methylcholanthrene, respectively, by rat liver microsomes.