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  • Title: Absolute configuration of trans-7,8-dihydroxy-7,8-dihydro-7-methylbenzo[a]pyrene enantiomer and the unusual quasidiequatorial conformation of the diacetate and dimenthoxyacetate derivatives.
    Author: Chiu PL, Fu PP, Weems HB, Yang SK.
    Journal: Chem Biol Interact; 1985 Jan; 52(3):265-77. PubMed ID: 3971469.
    Abstract:
    The enantiomers of trans-7,8-dihydroxy-7,8-dihydro-7-methylbenzo[a]pyrene (7-MBaP 7,8-dihydrodiol) and of trans-7,8-dihydroxy-7,8,9,10-tetrahydro-7-methylbenzo[a]pyrene (7-MBaP 7,8-tetrahydrodiol) were directly resolved by high-performance liquid chromatography (HPLC) using a commercially available column packed with an (R)-N-(3,5-dinitrobenzoyl)-phenylglycine derivative of gamma-aminopropylsilanized silica. The absolute configurations of the resolved enantiomers were determined by the exciton chirality method. Circular dichroism (CD) spectral analysis of the quasidiequatorial benzo[a]pyrene 7R,8R-dihydrodiol enantiomer and its diacetate and dimenthoxyacetate derivatives indicated conformational changes were induced upon derivatization. However, the characteristic CD Cotton effects of the quasidiequatorial 7-MBaP 7,8-dihydrodiol and its diacetate and dimenthoxyacetate derivatives were similar indicating that the conformation of 7-MBaP trans-7,8-dihydrodiol was not altered upon derivatization. Proton nuclear magnetic resonance (NMR) spectral analyses confirmed that 7-MBaP 7,8-dihydrodiol, its diacetate and dimenthoxyacetate derivatives all have quasidiequatorial conformations. The results indicate that the methyl substituent of 7-MBaP 7,8-dihydrodiol maintains a quasiaxial position regardless of the size of the acyl derivatives linked to the hydroxyl groups.
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