Acceleration of hydrolytic ring opening of N7-alkylguanine by the terminal carbamoyl group of glycidamide

Hydrolytic ring opening of guanine N7-adducts with compounds containing an oxacyclopropane ring, namely glycidamide, glycidol and 1,2-epoxybutane, was analyzed, and the reaction of the glycidamide adduct was the fastest. The differences in the reaction rates were confirmed by theoretical calculations. The hydrolytic ring opening of the N7 adduct of guanine in DNA was found to be affected by the terminal functional group. The reaction was analyzed by theoretical calculations.