Abstract
Through application of the exciton chirality method, absolute stereochemistry has been assigned to the (+)- and (−)-enantiomers of four of the five metabolically possible trans-dihydrodiols of the polycyclic hydrocarbon benzo[ a]anthracene (BA). The (+)- and (−)-enantiomers of each of these dihydrodiols can be separated as their diastereomeric bis-esters with (−)-α-methoxy-α-trifluoromethylphenylacetic acid by high pressure liquid chromatography (HPLC). BA 3,4-, 5,6-, 8,9- and 10,11-dihydrodiol are formed in 38%, 36%, 78% and 66% enantiomeric purity, respectively, by liver microsomes from phenobarbital-treated rats, whereas the liver microsomes from 3-methylcholanthrene(MC)-treated rats form BA 5,6-, 8,9- and 10,11-dihydrodiols with higher optical purity (62%, 96% and 96%, respectively). BA 3,4-dihydrodiol is formed from (±)-BA 3,4-oxide by microsomal epoxide hydrase in very high enantiometric purity (78%). The major enantiomer of the BA dihydrodiols formed by liver enzymes has R,R absolute stereochemistry in each case. In parallel with previous studies on the metabolism of benzo[ a]pyrene, the more tumorigenic (−)-enantiomer is the predominant isomer of BA 3,4-dihydrodiol formed by liver microsomes from BA.
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