SYNTHESIS OF 3-NITROBENZO[A]PYRENE BAY-REGION TRANS-7,8-DIOL ANTI-9,10-EPOXIDE AND THE CORRESPONDING N(2)-DEOXYGUANOSINE ADDUCT

3-Nitrobenzo[a]pyrene (3-nitro-BaP) is a potent mutagenic environmenta l contaminant, and its biological activities have been intensively stu died. It is significant to prepare its reactive metabolites and the co rresponding modified DNA adducts for biological studies. The synthesis of its oxidized proximate metabolite ns-7,8-dihydroxy-7,8-dihydro-3-n itrobenzo[a]pyrene (3-nitro-BaP-trans-7,8-dihydrodiol, 1), its oxidize d ultimate metabolite 10-epoxy-7,8,9,10-tetrahydro-3-nitrobenzo[a]pyre ne (3-nitro-BaP-DE, 2), and the corresponding DNA adduct ihydroxy-7,8, 9,10-tetrahydro-3-nitrobenzo[a]pyrene is described.