6533b860fe1ef96bd12c2dd8

RESEARCH PRODUCT

Direct optical resolution of trans-dihydrodiol enantiomers of fjord-region polycyclic aromatic hydrocarbons by high-performance liquid chromatography on a modified cellulose phase

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Abstract Enantioselective separation of trans -dihydrodiol metabolites of a series of fjord-region polycyclic aromatic hydrocarbons (PAHs), such as benzo[ c ]phenanthrene and dibenzo[ a , l ]pyrene, was evaluated by HPLC using commercially available cellulose-based CSPs as chiral columns. A baseline separation ( R s ≥1.6) with sharp, well-defined peaks of individual enantiomers was attained using cellulose-tris-( N -3,5-dimethylphenylcarbamate) and n -heptane-ethanol (9:1, v/v) as mobile phase. These chromatographic conditions permit a direct, simple and rapid (mostly within 30 min) enantiomeric resolution of PAH dihydrodiols. CD spectra were obtained for all optically pure enantiomers and absolute structure assignment was made for the hitherto unknown (+)- and (−)-enantiomers of naphtho[1,2- a ]pyrene9,10- and naphtho[1,2- e ]pyrene-11,12-dihydrodiol. The method appears to have great potential to be applied (i) in metabolism studies of fjord-region PAHs and (ii) for optical resolution of trans -dihydrodiol metabolites on a preparative scale.