Liquid Chromatographic Separation of FiveTrans-dihydrodiols of Benz[A] anthracene

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Abstract
Among the five possible trans-dihydrodiol derivatives of benz[a]anthracene (BA), trans-3,4- and trans-8,9-dihydrodiols could not be separated by either a normal-phase or a reversed-phase HPLC method unless they were first converted to diacetates. We describe in this report a complete separation of five BA trans-dihydrodiols using a Vydac C18 column and a column packed with a chiral stationary phase (R)-N-(3,5-dinitrobenzoyl) leucine covalently bonded to .gamma.-aminopropylsilanized silica. Enantiomeric compositions of BA 3,4-, 5,6-, 8,9-, and 10,11- trans-dihydrodiols formed in the metabolisms of Ba by liver microsomes from untreated, phenobarbital-treated, and 3-methylcholanthrene-treated rats were determined by chiral stationary phase HPLC or by comparing their circular dichroism spectral data with those of optically pure reference compounds.

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