Photochemical & Photobiological Sciences 2015-09-26

Pyrimidinone: versatile Trojan horse in DNA photodamage?

Mathias Micheel, Christian Torres Ziegenbein, Peter Gilch, Gerald Ryseck

Index: Photochem. Photobiol. Sci. 14 , 1598-606, (2015)

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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 ∼10(4) 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.

Related Compounds

  • Methanol
  • thf
  • Zebularine

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