Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.

[structure: see text]. trans-4-hydroxynonenal (4-HNE) is a unique product from the peroxidation of omega-6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The stereospecific syntheses of these four adducts has been achieved at the nucleoside level. The synthetic approach is amenable to the synthesis of structurally defined oligonucleotides containing these endogenous genotoxins.