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

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概要

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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.

• 2007-02-20

著者

• MIYAZAWA HIROSHI

  Department of Biotechnology, Faculty of Technology, Tokyo University of Agriculture and Technology

• Kino Katsuhito

  Department Of Pharmaceutical Technology Faculty Of Pharmaceutical Sciences At Kagawa Campus Tokushim

• Sugiyama Hiroshi

  Department Of Chemistry Graduate School Of Science Kyoto University

• Miyazawa Hiroshi

  Department Of Pharmaceutical Technology Faculty Of Pharmaceutical Sciences At Kagawa Campus Tokushim

• Miyazawa Hiroshi

  Department Of Biotechnology Faculty Of Technology Tokyo University Of Agriculture And Technology

• Sugiyama Hiroshi

  Department Of Chemistry Graduate School Of Science Kyoto University:sorst:science And Technology Age

• Sugiyama Hiroshi

  Department Of Chemistry Faculty Of Science

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