CHARACTERIZATION OF THE PRODUCTS FORMED IN THE REACTION BETWEEN 1,3-BUTADIENEMONOXIDE AND 2'-DEOXYADENOSINE BY LIQUID-CHROMATOGRAPHY CONTINUOUS-FLOW FAST-ATOM-BOMBARDMENT MASS-SPECTROMETRY

1,3-Butadiene, a widely produced industrial chemical, has recently bee n identified as a strong rodent carcinogen. Butadiene is metabolized t o reactive 3,4-epoxy-1-butene (BM), which may bind to DNA. The reactio n between 3,4-epoxy-1-butene and 2'-deoxyadenosine (dAdo) was studied. The reaction was carried out in trifluoroethanol-triethylamine and th e reaction mixture was analysed by liquid chromatography-continuous-fl ow fast atom bombardment mass spectrometry. The recorded total-ion chr omatogram showed four peaks. The spectra of the peaks exhibited a prot onated molecule of BM adducts of dAdo (m/z 322), indicating formation of different isomers of the adducts. One alkylation site was shown to be at the exocyclic amino group of the 2'-deoxyadenosine.