Efficient Incorporation of a Copper Hydroxypyridone Base Pair in DNA
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- Kentaro Tanaka
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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- Atsushi Tengeiji
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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- Tatsuhisa Kato
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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- Namiki Toyama
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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- Motoo Shiro
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
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- Mitsuhiko Shionoya
- Contribution from the Department of Chemistry, Graduate School of Science, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan, Institute for Molecular Science, Myodaiji, Okazaki 444-8585, Japan, and Rigaku Corporation, 3-9-12 Matsubaracho, Akishima, Tokyo 196-8666, Japan
書誌事項
- 公開日
- 2002-09-25
- DOI
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- 10.1021/ja027175o
- 公開者
- American Chemical Society (ACS)
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説明
Recently, we reported the first artificial nucleoside for alternative DNA base pairing through metal complexation (J. Org. Chem. 1999, 64, 5002-5003). In this regard, we report here the synthesis of a hydroxypyridone-bearing nucleoside and the incorporation of a neutral Cu(2+)-mediated base pair of hydroxypyridone nucleobases (H-Cu-H) in a DNA duplex. When the hydroxypyridone bases are incorporated into the middle of a 15 nucleotide duplex, the duplex displays high thermal stabilization in the presence of equimolar Cu(2+) ions in comparison with a duplex containing an A-T pair in place of the H-H pair. Monitoring temperature dependence of UV-absorption changes verified that a Cu(2+)-mediated base pair is stoichiometrically formed inside the duplex and dissociates upon thermal denaturation at elevated temperature. In addition, EPR and CD studies suggested that the radical site of a Cu(2+) center is formed within the right-handed double-strand structure of the oligonucleotide. The present strategy could be developed for controlled and periodic spacing of neutral metallobase pairs along the helix axis of DNA.
収録刊行物
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- Journal of the American Chemical Society
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Journal of the American Chemical Society 124 (42), 12494-12498, 2002-09-25
American Chemical Society (ACS)

