| ○種別 (必須): | □ | 学術論文 (審査論文)
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| ○言語 (必須): | □ | 英語
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| ○招待 (推奨): |
| ○審査 (推奨): | □ | Peer Review
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| ○カテゴリ (推奨): | □ | 研究
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| ○共著種別 (推奨): |
| ○学究種別 (推奨): | □ | 博士前期課程学生による研究報告
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| ○組織 (推奨): | 1. | 徳島大学.薬学研究科 (2004年4月1日〜)
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| 2. | 徳島大学.大学院ヘルスバイオサイエンス研究部.創薬資源科学部門.機能分子創製学講座.機能分子合成薬学 (2004年4月1日〜2015年3月31日)
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| 3. | 徳島大学.薬学部.創製薬科学科.創薬学講座.機能分子合成薬学 (2006年4月1日〜)
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| 4. | 徳島大学.大学院ヘルスバイオサイエンス研究部.薬学系・総合薬学センター.総合薬学研究推進室 (〜2015年3月31日)
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| ○著者 (必須): | 1. | (英) Miyajima Rin (日) 宮島 凜 (読) みやじま りん
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| ○学籍番号 (推奨): | □ | ****
| [ユーザ] |
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| 2. | (英) Tsuda Yusuke (日) 津田 雄介 (読) つだ ゆうすけ
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| ○貢献度 (任意): |
| ○学籍番号 (推奨): | □ | ****
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| 3. | 猪熊 翼 ([徳島大学.大学院医歯薬学研究部.薬学域.薬科学部門.創薬科学系.薬品製造化学])
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| ○貢献度 (任意): |
| ○学籍番号 (推奨): |
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| 4. | 重永 章
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| 5. | (英) Imanishi Miki (日) 今西 未来 (読)
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| ○貢献度 (任意): |
| ○学籍番号 (推奨): |
| [継承] |
| 6. | (英) Futaki Shiro (日) 二木 史朗 (読)
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| ○貢献度 (任意): |
| ○学籍番号 (推奨): |
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| 7. | 大髙 章 ([徳島大学.大学院医歯薬学研究部.薬学域.薬科学部門.創薬科学系.機能分子合成薬学])
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| ○貢献度 (任意): |
| ○学籍番号 (推奨): |
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| ○題名 (必須): | □ | (英) Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis (日)
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| ○副題 (任意): |
| ○要約 (任意): | □ | (英) The vital roles of peptide/protein thioesters in protein chemistry, including chemical or semi-synthesis of proteins, have encouraged studies on the development of methods for the preparation of such chemical units. Biochemical protocols using intein or sortase have proved to be useful in protein chemistry as methods suitable for naturally occurring sequences, including recombinant proteins. Although chemical protocols are potential options for thioester preparation, only a few are applicable to naturally occurring sequences, because standard chemical protocols require an artificial chemical device for producing thioesters. In this context, the chemical preparation of thioesters based on a reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis was investigated. Regioselective S-cyanylation, which is required for cysteine-containing thioesters, was achieved with the aid of a zinc-complex formation of a CCHH-type zinc-finger sequence. Free cysteine residues that are not involved in complex formation were selectively protected with a 6-nitroveratryl group followed by S-cyanylation of the zinc-binding cysteine. Hydrazinolysis of the resulting S-cyanopeptide and subsequent photo-removal of the 6-nitroveratryl group yielded the desired peptide hydrazide, which was then converted to the corresponding thioester. The generated thioester was successfully used in N-to-C-directed one-pot/sequential native chemical ligation using an N-sulfanylethylanilide peptide to give a 64-residue peptide toxin. © 2015 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 106: 531-546, 2016. (日)
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| ○キーワード (推奨): |
| ○発行所 (推奨): |
| ○誌名 (必須): | □ | Biopolymers (American Peptide Society)
(pISSN: 0006-3525, eISSN: 1097-0282)
| ○ISSN (任意): | □ | 1097-0282
ISSN: 0006-3525
(pISSN: 0006-3525, eISSN: 1097-0282) Title: BiopolymersTitle(ISO): BiopolymersPublisher: Wiley (NLM Catalog)
(Wiley)
(Scopus)
(CrossRef)
(Scopus information is found. [need login]) | [継承] |
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| ○巻 (必須): | □ | 106
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| ○号 (必須): | □ | 4
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| ○頁 (必須): | □ | 531 546
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| ○都市 (任意): |
| ○年月日 (必須): | □ | 西暦 2015年 10月 26日 (平成 27年 10月 26日)
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| ○URL (任意): |
| ○DOI (任意): | □ | 10.1002/bip.22757 (→Scopusで検索)
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| ○PMID (任意): | □ | 26501985 (→Scopusで検索)
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| ○CRID (任意): |
| ○WOS (任意): |
| ○Scopus (任意): |
| ○機関リポジトリ : | □ | 111898
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| ○評価値 (任意): |
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| ○指導教員 (推奨): |
| ○備考 (任意): | 1. | (英) Article.ELocationID: 10.1002/bip.22757 (日)
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| 2. | (英) Article.PublicationTypeList.PublicationType: Journal Article (日)
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| 3. | (英) KeywordList.Keyword: S-cyanylation (日)
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| 4. | (英) KeywordList.Keyword: hydrazinolysis (日)
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| 5. | (英) KeywordList.Keyword: native chemical ligation (日)
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| 6. | (英) KeywordList.Keyword: thioester (日)
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