『徳島大学 教育・研究者情報データベース (EDB)』---[学外] /
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EID=291046EID:291046, Map:0, LastModified:2015年3月3日(火) 21:04:02, Operator:[山田 久嗣], Avail:TRUE, Censor:0, Owner:[山田 久嗣], Read:継承, Write:継承, Delete:継承.
種別 (必須): 学術論文 (審査論文) [継承]
言語 (必須): 英語 [継承]
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組織 (推奨):
著者 (必須): 1.山田 久嗣 ([徳島大学.大学院社会産業理工学研究部.生物資源産業学域.応用生命系.応用生物資源学分野]/[徳島大学.生物資源産業学部.生物資源産業学科.応用生命講座])
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2. (英) Kitauchi Yuya (日) (読)
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[継承]
3. (英) Tanabe Kazuhito (日) (読)
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[継承]
4. (英) Ito Takeo (日) (読)
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5. (英) Nishimoto Sei-Ichi (日) (読)
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題名 (必須): (英) Anthraquinone-sensitized photooxidation of 5-methylcytosine in DNA leading to piperidine-induced efficient strand cleavage.  (日)    [継承]
副題 (任意):
要約 (任意): (英) One-electron photooxidations of 5-methyl-2'-deoxycytidine (d(m)C) and 5-trideuteriomethyl-2'-deoxycytidine ([D(3)]d(m)C) by sensitization with anthraquinone (AQ) derivatives were investigated. Photoirradiation of an aerated aqueous solution containing d(m)C and anthraquinone 2-sulfonate (AQS) afforded 5-formyl-2'-deoxycytidine (d(f)C) and 5-hydroxymethyl-2'-deoxycytidine (d(hm)C) in good yield through an initial one-electron oxidation process. The deuterium isotope effect on the AQS-sensitized photooxidation of d(m)C suggests that the rate-determining step in the photosensitized oxidation of d(m)C involves internal transfer of the C5-hydrogen atom of a d(m)C-tetroxide intermediate to produce d(f)C and d(hm)C. In the case of a 5-methylcytosine ((m)C)-containing duplex DNA with an AQ chromophore that is incorporated into the backbone of the DNA strand so as to be immobilized at a specific position, (m)C underwent efficient direct one-electron oxidation by the photoexcited AQ, which resulted in an exclusive DNA strand cleavage at the target (m)C site upon hot piperidine treatment. In accordance with the suppression of the strand cleavage at 5-trideuterio-methylcytosine observed in a similar AQ photosensitization, it is suggested that deprotonation at the C5-methyl group of an intermediate (m)C radical cation may occur as a key elementary reaction in the photooxidative strand cleavage at the (m)C site. Incorporation of an AQ sensitizer into the interior of a strand of the duplex enhanced the one-electron photooxidation of (m)C, presumably because of an increased intersystem crossing efficiency that may lead to efficient piperidine-induced strand cleavage at an (m)C site in a DNA duplex.  (日)    [継承]
キーワード (推奨): 1. (英) Anthraquinones (日) (読) [継承]
2. (英) DNA (日) (読) [継承]
3. (英) DNA Cleavage (日) (読) [継承]
4. (英) DNA Methylation (日) (読) [継承]
5. (英) Deoxycytidine (日) (読) [継承]
6. (英) Electrons (日) (読) [継承]
7. (英) Molecular Structure (日) (読) [継承]
8. (英) Oxidation-Reduction (日) (読) [継承]
9. (英) Photochemistry (日) (読) [継承]
10. (英) Piperidines (日) (読) [継承]
11. (英) Solutions (日) (読) [継承]
12. (英) Water (日) (読) [継承]
発行所 (推奨):
誌名 (必須): Chemistry - A European Journal ([Wiley-VCH])
(pISSN: 0947-6539, eISSN: 1521-3765)

ISSN (任意): 1521-3765
ISSN: 0947-6539 (pISSN: 0947-6539, eISSN: 1521-3765)
Title: Chemistry (Weinheim an der Bergstrasse, Germany)
Title(ISO): Chemistry
Supplier: Chemistry Europe
Publisher: Wiley
 (NLM Catalog  (Wiley  (Scopus  (CrossRef (Scopus information is found. [need login])
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(必須): 17 [継承]
(必須): 7 [継承]
(必須): 2225 2235 [継承]
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年月日 (必須): 西暦 2011年 1月 14日 (平成 23年 1月 14日) [継承]
URL (任意):
DOI (任意): 10.1002/chem.201001884    (→Scopusで検索) [継承]
PMID (任意): 21294186    (→Scopusで検索) [継承]
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備考 (任意): 1.(英) PublicationType: Journal Article  (日)    [継承]
2.(英) PublicationType: Research Support, Non-U.S. Gov't  (日)    [継承]

標準的な表示

和文冊子 ● Hisatsugu Yamada, Yuya Kitauchi, Kazuhito Tanabe, Takeo Ito and Sei-Ichi Nishimoto : Anthraquinone-sensitized photooxidation of 5-methylcytosine in DNA leading to piperidine-induced efficient strand cleavage., Chemistry - A European Journal, Vol.17, No.7, 2225-2235, 2011.
欧文冊子 ● Hisatsugu Yamada, Yuya Kitauchi, Kazuhito Tanabe, Takeo Ito and Sei-Ichi Nishimoto : Anthraquinone-sensitized photooxidation of 5-methylcytosine in DNA leading to piperidine-induced efficient strand cleavage., Chemistry - A European Journal, Vol.17, No.7, 2225-2235, 2011.

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