8-Oxopurines are biological molecules with interesting redox properties that play important roles in DNA oxidative damage, DNA-protein cross-linking and antioxidation defense. Among them, 8-oxoguanosine (OG) is considered as a biomarker of oxidative stress. One-electron oxidation of OG has been studied for years andspiroiminodihydantoin (Sp) or guanidinohydantoin (Gh) have been characterized as the major products depending on the oxidation conditions. Here, we describe the one-electron oxidation of uric acid nucleoside (RU), the deamination product of OG. Itwas found that replacement of the exocyclic amine group by the oxo group at C2of OG had a significant effect on the decomposition pathways of the 5-hydroxylated intermediate. Unlike the OG pathway, 5-OH-RU undergoes H2O addition at C4 leading to 3 products: HICA amide, caffolide and urea nucleosides, instead of the spirocyclic product. Some mechanistic explanations for these facts will be discussed.The facile oxidation of OG and RU suggest they could play a role in reversal of photochemical damage, such as thymine dimers in DNA. Results toward these goals will also be presented

Redoxchemistry of 8-oxopurine nucleosides and their potential role in mitigating photochemical damage in DNA

240th National Meeting (2010)

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