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Carbonium ion as ultimate carcinogen of polycyclic aromatic hydrocarbons

Abstract

RECENT results have indicated that the proximate metabolites of benzo(α)pyrene1 and benz(α)anthracene2,3, two typical carcinogenic aromatic hydrocarbons, contain the 1,2-epoxy-3, 4-dihydroxy-tetrahydronaphthalene moiety. This moiety arises from its parent hydrocarbon by formation of an arene oxide, enzymatic ring opening of this oxide to a diol, and then a second epoxidation. As the initially formed arene oxide is opened in a trans fashion4, only two geometrical isomers for the proximate metabolite are possible, and these are depicted as partial structures (I) and (II).

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HULBERT, P. Carbonium ion as ultimate carcinogen of polycyclic aromatic hydrocarbons. Nature 256, 146–148 (1975). https://doi.org/10.1038/256146a0

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