User-friendly Synthesis and Photoirradiation of a Flavin-linked Oligomer

DOI Web Site 被引用文献9件 参考文献25件
  • Kino Katsuhito
    Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Miyazawa Hiroshi
    Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
  • Sugiyama Hiroshi
    Department of Chemistry, Graduate School of Science, Kyoto University SORST, Japan Science and Technology Agency

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Photosensitized oxidation of guanine provides various oxidation products, including 8-oxoguanine (8-oxoG) and imidazolone. Riboflavin (vitamin B2) is known as an effective photosensitizer for oxidation of guanine. Here, we show the user-friendly synthesis and photoreaction of a flavin-linked oligonucleotide; the practical synthesis of a hydroxyethyl-flavin (2) from commercially available riboflavin; and the preparation of a flavin-linked oligonucleotide using the phosphoramidite of 2. To demonstrate the usefulness of this method, the flavin-linked oligomer flavin-5′-d(T6CCT6)-3′ was synthesized. Flavin-5′-d(T6CCT6)-3′ and its complementary 5′-d(A6G8-oxoGA6)-3′ were irradiated under UV light (366 nm) at neutral pH. Enzymatic digestion of the irradiated mixture with P1 nuclease and alkaline phosphatase indicated that the 8-oxoG residue was oxidized to imidazolone. These results demonstrate that 8-oxoG is effectively oxidized to imidazolone by photosensitization of the terminal flavin via a hole-transfer mechanism, and imidazolone is formed by one-electron oxidation of 8-oxoG at neutral pH.<br>

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