Synthesis and structure determination of the adducts of dibenzo[a,f]pyrene diol epoxides and deoxyadenosine or deoxyguanosine

(±)-5yn-dibenzo[a, l]pyrene diol epoxide (DB[a,l]PDE) and (+)-anti-DB[a,[]?DE were reacted with deoxyadenosine (dA) or deoxyguanosine (dG) in dimethylformamide at 100 °C for 30 min. The crude products were purified by reverse phase HPLC under gradient and isocratic conditions. The structure of each adduct was assigned by 1D and 2D NMR spectra and by fast atom bombardment mass spectrometry. Five adducts were isolated from the reaction of (±)-s)w-DB[a,/]PDE and dA: yy/j-DBta^PDE-N^A-1,. syn-DB[fl,/]PDE-N6dA-2,. yy/z-DB[a,/]PDE-N6dA-3,. yjw-DBfoqPDE-NftiA^ and. yytf-DB[a,/]PDE-N7Ade. Four adducts were isolated from the reaction of (±)-anti-DB[a,{]PDE and dA: anri-DB[a,f]PDE-^6A~, anti-DB[a,/]PDE-N6d A-2, fl/7//-DB[tf,/]PDE-N6dA~3 and tfAW-DB[r/,/]PDE-N6dA-4. Two adducts were isolated from the reaction of (±)-.vy/?-DB[fl,/]PDE and dG: (±)-11,12, n-trihydroxy-tetrahydroDBtcG/JP-M-NfdG and (±)-11,12,13-trihydroxy-tetrahydroDB[a,/]P-14-N7Gua. Two adducts were isolated from the reaction of {±yanri-DB[a>l]PDE and dG: (±)-11,12,13-trihydroxy-tetra-hydroDB[a,/]P-14-N2dG and (±)-11, ^O-trihydroxy-tetrahydroDB^/lP-M-^Gua.