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Issue 9, 2015
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Pyrimidinone: versatile Trojan horse in DNA photodamage?

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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 ∼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.

Graphical abstract: Pyrimidinone: versatile Trojan horse in DNA photodamage?

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Article information


Submitted
23 Mar 2015
Accepted
22 Jun 2015
First published
08 Jul 2015

This article is Open Access

Photochem. Photobiol. Sci., 2015,14, 1598-1606
Article type
Paper
Author version available

Pyrimidinone: versatile Trojan horse in DNA photodamage?

M. Micheel, C. Torres Ziegenbein, P. Gilch and G. Ryseck, Photochem. Photobiol. Sci., 2015, 14, 1598
DOI: 10.1039/C5PP00114E

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