Abstract
(6-4) Photolesions between adjacent pyrimidine DNA bases are prone to secondary photochemistry. It has been shown that singlet excited (6-4) moieties form Dewar valence isomers as well as triplet excitations. We here report on the triplet state of a minimal model for the (6-4) photolesion, 1-methyl-2(1H)-pyrimidinone. Emphasis is laid on its ability to abstract hydrogen atoms from alcohols and carbohydrates. Steady-state and time-resolved experiments consistently yield bimolecular rate constants of ∼104 M−1 s−1 for the hydrogen abstraction. The process also occurs intramolecularly as experiments on zebularine (1-(β-d-ribofuranosyl)-2(1H)-pyrimidinone) show.
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Micheel, M., Ziegenbein, C.T., Gilch, P. et al. Pyrimidinone: versatile Trojan horse in DNA photodamage?. Photochem Photobiol Sci 14, 1598–1606 (2015). https://doi.org/10.1039/c5pp00114e
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DOI: https://doi.org/10.1039/c5pp00114e