Flavin-sensitized photoreduction of thymidine glycol.

Takeo Ito, Akiko Kondo, Satoru Terada, Sei-ichi Nishimoto

Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto, Japan. takeoit@sci.kyoto-u.ac.jp

Bioorganic & medicinal chemistry letters 2007 Nov 15

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Photochemical reactivity of flavin adenine dinucleotide (FAD) and flavin mononucleotide (FMN) toward thymidine glycol (dTg) has been investigated. Fluorescence intensity of FAD was enhanced as increasing the concentration of dTg, suggesting that adenosine moiety of FAD interacts with dTg. However, photoreduction of dTg using reduced form of FAD gave repaired thymidine in almost the same yield as when reduced FMN was used alternatively, and thus such interaction seems to have no effect on the reduction. Oligodeoxynucleotides containing dTg were also photochemically repaired by reduced form of flavins in different yields depending on the sequence, which could be related to electron affinity of the nucleobases in DNA.

Citation

Takeo Ito, Akiko Kondo, Satoru Terada, Sei-ichi Nishimoto. Flavin-sensitized photoreduction of thymidine glycol. Bioorganic & medicinal chemistry letters. 2007 Nov 15;17(22):6129-33