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Mammalian metabolism of polycyclic aromatic hydrocarbons results in the formation of vicinal diol epoxides (existing as enantiomeric pairs of two diastereomers) considered as important ultimate carcinogens if the oxirane ring is located in a bay or fjord region of the parent hydrocarbon. In the present study, individual stereoisomers of the bay region diol epoxides of chrysene, dibenz[a,h]-anthracene and benzo[a]pyrene, as well as of the fjord region diol epoxides of benzo[c]phenanthrene, benzo[g] chrysene and have beenzo[g] incubated with glutathione (GSH) in the presence or absence of human glutathione S-transferase isoenzyme GST A1-1, a class Alpha enzyme. The formation of GSH conjugates was determined and quantified by HPLC. The results demonstrate that the GST A1-1 isoenzyme catalyzes the formation of GSH conjugates of all diol epoxides tested, although a marked variation in catalytic efficiency (&gt;20-fold) was observed. With both bay and fjord regionanti-diol epoxides a significant preference for conjugation of the enantiomer with theRconfiguration at the benzylic position of the oxirane ring was noted. Among thesyndiastereomers of

carcinogenesis

CARCINOGENESIS: Glutathione S-transferase A1–1-catalysed conjugation of bay and fjord region diol epoxides of polycyclic aromatic hydrocarbons with glutathione