徳島大学 教育・研究者情報データベース(EDB)

1. 徳島大学.薬学研究科(2004年4月1日〜)
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)
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〜)
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)

1. (英) Miyajima Rin / (日) 宮島 凜 / (読) みやじま りん

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2. (英) Tsuda Yusuke / (日) 津田 雄介 / (読) つだ ゆうすけ

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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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4. 重永 章

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5. (英) Imanishi Miki / (日) 今西 未来

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6. (英) Futaki Shiro / (日) 二木 史朗

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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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(英) Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis

(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.

1. (英) Article.ELocationID: 10.1002/bip.22757

2. (英) Article.PublicationTypeList.PublicationType: Journal Article

3. (英) KeywordList.Keyword: S-cyanylation

4. (英) KeywordList.Keyword: hydrazinolysis

5. (英) KeywordList.Keyword: native chemical ligation

6. (英) KeywordList.Keyword: thioester