A novel method of preparing amine-modifying C-4' oxidized nucleotide

A novel method of preparing C-4' oxidized nucleotide, a monomeric model of an alkali labile lesion (1) has been studied. The C-4' selenated 4a and 4b were found to be effective in preparing 3, a monomeric model of 1, by the reaction with NBS (N-bromosuccinimide). The successive reaction of 3 with amine at room temperature afforded the α,β-unsaturated γ-methylene-γ-lactam (2) in good yield.