Resolution of optical isomers by high-pressure liquid chromatography: The separation of benzo[a]pyrene trans-diol derivatives

The optical isomers of (±)r-7,t-8-dihydroxy-7,8-dihydrobenzoa]pyrene and its synthetic precursor (±)r-7,t-8-dihydroxy-7,8,9,10-tetrahydrobenzoa]pyrene were resolved as their di-(−)menthoxyacetates using high-pressure liquid chromatography. Saponification of the resolved diesters yielded the corresponding enantiomers. The specific rotation, CD spectra, and ORD curves are reported. The resolution of these optical isomers permits detailed studies on the enzymatic intermediates and the mechanism of benzoa]pyrene activation to its carcinogenic form. The method is of general usefulness for the resolution of optical isomers.