User-friendly Synthesis and Photoirradiation of a Flavin-linked Oligomer
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- Kino Katsuhito
- Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
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- Miyazawa Hiroshi
- Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University
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- Sugiyama Hiroshi
- Department of Chemistry, Graduate School of Science, Kyoto University SORST, Japan Science and Technology Agency
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説明
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>
収録刊行物
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- Genes and Environment
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Genes and Environment 29 (1), 23-28, 2007
日本環境変異原学会
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詳細情報 詳細情報について
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- CRID
- 1390001205258004736
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- NII論文ID
- 130004481152
- 110006240240
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- NII書誌ID
- AA1212552X
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- ISSN
- 18807062
- 18807046
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- NDL書誌ID
- 8662205
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDLサーチ
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