Novel trifluoroethanol mediated synthesis of benzo[a]pyrene 7,8-diol 9,10-epoxide adducts at the N2-position of deoxyguanosine and the N6-position of deoxyadenosine

The exocyclic amino groups of deoxyadenosine and deoxyguanosine readily add to C-10 of the benzo[a]pyrene 7,8-diol 9,10-epoxides at room temperature overnight in trifluoroethanol. Whereas the dG adducts are obtained as a mixture of cis- and trans-opened diastereomers, the dA adducts arise exclusively by cis-opening.