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Prediction of thymine dimer repair by electron transfer from photoexcited 8-aminoguanine or its deprotonated anion.

Electronic structure methods are used to estimate differences in reaction barriers for transfer of an electron from singlet ππ* excited 8-aminoguanine (A) or deprotonated 8-aminoguanine anion (A(-)) to a proximal thymine dimer site compared to barriers when ππ* excited 8-oxoguanine (O) or deprotonated 8-oxoguanine (O(-)) serve as the electron donor. It is predicted that the barrier for photoexcited A should be lower than for photoexcited O, and the barrier for photoexcited A(-) should be lower than for photoexcited O(-). Moreover, A, O(-), and A(-) are predicted to have ππ* excited states at energies near where O does, which allows them to be excited by photons low enough in energy to avoid exciting or ionizing any of DNA's bases. The origin of the differences in barriers is suggested to be the lower ionization potential of A compared to O and the lower electron detachment energy of A(-) compared to O(-). Because O and O(-) have been experimentally shown to produce thymine dimer repair, it is proposed that A and A(-) are promising repair agents deserving experimental study.