User-friendly Synthesis and Photoirradiation of a Flavin-linked Oligomer
نویسندگان
چکیده
Photosensitized oxidation of guanine provides various oxidation products, including 8-oxoguanine (8-oxoG) and imidazolone. Ribo‰avin (vitamin B2) is known as an eŠective photosensitizer for oxidation of guanine. Here, we show the user-friendly synthesis and photoreaction of a ‰avin-linked oligonucleotide; the practical synthesis of a hydroxyethyl-‰avin (2) from commercially available ribo‰avin; and the preparation of a ‰avin-linked oligonucleotide using the phosphoramidite of 2. To demonstrate the usefulness of this method, the ‰avin-linked oligomer ‰avin-5?-d(T6CCT6)-3? was synthesized. Flavin5?-d(T6CCT6)-3? and its complementary 5?-d(A6G8oxoGA6)-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 eŠectively oxidized to imidazolone by photosensitization of the terminal ‰avin via a hole-transfer mechanism, and imidazolone is formed by one-electron oxidation of 8-oxoG at neutral pH.
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