Abasic sites are common in cellular and synthetic DNA. As a result, it is important to characterize the chemical fate of these lesions. Amine-catalyzed strand cleavage at abasic sites facilitates β-elimination of the 3′-phosphoryl group to generate trans-α,β-unsaturated aldehyde sugar remnant. Although a handful of studies have reported 3′-sugar remnants generated by amine-catalyzed strand cleavage, the formation and properties of these products are not well-understood. To address this knowledge gap, a nucleoside system was developed that enabled chemical characterization of the sugar remnants generated by amine-catalyzed β-elimination in the 2-deoxyribose system. The model reactions provide evidence that the products generated by amine-catalyzed strand cleavage at abasic sites in cellular DNA may be more complex that commonly thought, with trans-α,β-unsaturated iminium ion intermediates residing at the hub of interconverting product mixtures.

Products generated by amine-catalyzed strand cleavage at abasic site in duplex DNA

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