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Development of a stimulus-responsive amino acid that enables functional control of peptides and proteins

Research Project

Project/Area Number 15K07858
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionThe University of Tokushima

Principal Investigator

SHIGENAGA Akira  徳島大学, 大学院医歯薬学研究部(薬学域), 講師 (10423394)

Co-Investigator(Renkei-kenkyūsha) OTAKA Akira  徳島大学, 大学院医歯薬学研究部(薬学域), 教授 (20201973)
INOKUMA Tsubasa  徳島大学, 大学院医歯薬学研究部(薬学域), 助教 (40541272)
Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywordsトリメチルロック / 機能制御 / ペプチド / タンパク質 / 刺激応答 / ラクトン化 / アミド結合切断 / ペプチド結合切断 / 活性制御 / 刺激応答型アミノ酸
Outline of Final Research Achievements

A stimulus-responsive amino acid, which induces stimulus-triggered amide/peptide bond cleavage, enables functional control of peptides and proteins. In this project, we challenged to accelerate the amide bond cleavage of the stimulus-responsive unit that should be the bases for practical stimulus-responsive amino acids. We first established a fluorescence-based system to easily monitor the amide bond cleavage. Then, several new stimulus-responsive units were synthesized and their kinetics of the amide bond cleavage was evaluated based on the fluorescence monitoring. Finally, we successfully found out a new stimulus-responsive unit, its amide bond cleavage is significantly accelerated under acid conditions.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (32 results)

All 2018 2017 2016 2015 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Open Access: 11 results,  Acknowledgement Compliant: 7 results) Presentation (16 results) (of which Int'l Joint Research: 2 results,  Invited: 5 results) Remarks (3 results)

  • [Journal Article] ProteoFind: A script for finding proteins that are suitable for chemical synthesis2018

    • Author(s)
      Shigenaga, A.; Naruse, N.; Otaka, A.
    • Journal Title

      Tetrahedron

      Volume: 74 Issue: 19 Pages: 2291-2297

    • DOI

      10.1016/j.tet.2018.03.030

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Elucidation of inhibitor-binding pocket of D-amino acid oxidase using docking simulation and N-sulfanylethylanilide-based labeling technology2017

    • Author(s)
      Taiki Kohiki, Yusuke Kato, Yusuke Nishikawa, Kazuko Yorita, Ikuko Sagawa, Masaya Denda, Tsubasa Inokuma, Akira Shigenaga*, Kiyoshi Fukui*, Akira Otaka*
    • Journal Title

      Org. Biomol. Chem. (Inside Front Cover)

      Volume: 15 Issue: 25 Pages: 5289-5297

    • DOI

      10.1039/c7ob90109g

    • NAID

      120006493365

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Chemical Synthetic Platform for Chlorpromazine Oligomers That Were Reported as Photo-degradation Products of Chlorpromazine2017

    • Author(s)
      Kohiki Taiki、Nishikawa Yusuke、Inokuma Tsubasa、Shigenaga Akira、Otaka Akira
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 65 Issue: 12 Pages: 1161-1166

    • DOI

      10.1248/cpb.c17-00692

    • NAID

      130006235035

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Invention of stimulus-responsive peptide-bond-cleaving residue (Spr) and its application to chemical biology tools2017

    • Author(s)
      Akira Shigenaga*, Jun Yamamoto, Taiki Kohiki, Tsubasa Inokuma, Akira Otaka*
    • Journal Title

      J. Pept. Sci. (Akabori Special Issue, Review)

      Volume: 23 Issue: 7-8 Pages: 505-513

    • DOI

      10.1002/psc.2961

    • NAID

      120006493367

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Development of an anilide type scaffold for the thioester precursor N-sulfanylethylcoumarynyl amide.2016

    • Author(s)
      Eto, M.; Naruse, N.; Morimoto, K.; Yamaoka, K.; Sato, K.; Tsuji, K.; Inokuma, T.; Shigenaga, A.; Otaka, A.
    • Journal Title

      Org. Lett.

      Volume: 18 Issue: 17 Pages: 4416-4419

    • DOI

      10.1021/acs.orglett.6b02207

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Labelling of endogenous target protein via N-S acyl transfer-mediated activation of N-sulfanylethylanilide2016

    • Author(s)
      Denda, M.; Morisaki, T.; Kohiki, T.; Yamamoto, J.; Sato, K.; Sagawa, I.; Inokuma, T.; Sato, Y.; Yamauchi, A.; Shigenaga, A.*; Otaka, A.*
    • Journal Title

      Org. Biomol. Chem.

      Volume: 14 Issue: 26 Pages: 6244-6251

    • DOI

      10.1039/c6ob01014h

    • NAID

      120006489009

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] An N-Sulfanylethylanilide-based traceable linker for enrichment and selective labelling of target proteins2016

    • Author(s)
      Takuya Morisaki, Masaya Denda, Jun Yamamoto, Daisuke Tsuji, Kohji Itoh, Tsubasa Inokuma, Akira Shigenaga and Akira Otaka
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 42 Pages: 6911-6913

    • DOI

      10.1039/c6cc01229a

    • NAID

      120006493363

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access
  • [Journal Article] Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis2016

    • Author(s)
      Rin Miyajima, Yusuke Tsuda, Tsubasa Inokuma, Akira Shigenaga, Miki Imanishi, Shiro Futaki and Akira Otaka
    • Journal Title

      Biopolymers

      Volume: - Issue: 4 Pages: 531-546

    • DOI

      10.1002/bip.22757

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] One-pot/sequential native chemical ligation using photo-caged crypto-thioester2016

    • Author(s)
      Keisuke Aihara, Kosuke Yamaoka, Naoto Naruse, Tsubasa Inokuma, Akira Shigenaga and Akira Otaka
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 3 Pages: 596-599

    • DOI

      10.1021/acs.orglett.5b03661

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile Preparation of Peptides with C-Terminal <i>N</i>-Alkylamide <i>via</i> Radical-Initiated Dethiocarboxylation2016

    • Author(s)
      Shimizu, T.; Miyajima, R.; Naruse, N.; Yamaoka, K.; Aihara, K.; Shigenaga, A.*; Otaka, A.*
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 64 Issue: 4 Pages: 375-378

    • DOI

      10.1248/cpb.c15-01025

    • NAID

      130005141024

    • ISSN
      0009-2363, 1347-5223
    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile synthesis of C-terminal peptide thioacids under mild conditions from N-sulfanylethylanilide peptides2016

    • Author(s)
      Shimizu, T.; Miyajima, R.; Sato, K.; Sakamoto, K.; Naruse, N.; Kita, M.; Shigenaga, A.*; Otaka, A.*
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 7 Pages: 992-998

    • DOI

      10.1016/j.tet.2015.12.070

    • NAID

      120006493362

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Development of an intein-inspired amide cleavage chemical device2016

    • Author(s)
      Komiya, C.; Aihara, K.; Morishita, K.; Ding, H.; Inokuma, T.; Shigenaga, A.; Otaka, A.*
    • Journal Title

      J. Org. Chem.

      Volume: 81 Issue: 2 Pages: 699-707

    • DOI

      10.1021/acs.joc.5b02399

    • NAID

      120006493349

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Design and synthesis of a hydrogen peroxide-responsive amino acid that induces peptide bond cleavage after exposure to hydrogen peroxide2015

    • Author(s)
      Kita, M.; Yamamoto, J.; Morisaki, T.; Komiya, C.; Inokuma, T.; Miyamoto, L.; Tsuchiya, K.; Shigenaga, A.*; Otaka, A.*
    • Journal Title

      Tetrahedron Lett.

      Volume: 56 Issue: 28 Pages: 4228-4231

    • DOI

      10.1016/j.tetlet.2015.05.060

    • NAID

      120006493359

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] アシル基転移反応を基盤とする標的タンパク質精製・機能解明ツールの開発2018

    • Author(s)
      重永 章、大高 章
    • Organizer
      日本薬学会第138年会(シンポジウム 中分子創薬研究のフロンティア)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] N-Sulfanylethylanilideを用いた細胞内標的タンパク質ラベル化法の開発2017

    • Author(s)
      古曳泰規、傳田将也、藤川昴樹、猪熊 翼、重永 章、小暮健太朗、大高 章
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      東北大学(宮城県仙台市)
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] アミド結合切断反応を基盤とした生命科学指向型ツールの開発2017

    • Author(s)
      重永 章
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] タンパク質位置選択的修飾を指向したチオエステル調製法の開発2016

    • Author(s)
      津田雄介、重永 章、辻 耕平、傳田将也、佐藤浩平、北風圭介、中村太寛、猪熊 翼、伊藤孝司、大高 章
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば国際会議場(茨城県つくば市)
    • Year and Date
      2016-11-30
    • Related Report
      2016 Research-status Report
  • [Presentation] SEAlideを基盤とした標的タンパク質精製ツールの開発研究2016

    • Author(s)
      森崎巧也、傳田将也、辻 大輔、山本 純、猪熊 翼、伊藤孝司、重永 章、大高 章
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば国際会議場(茨城県つくば市)
    • Year and Date
      2016-11-30
    • Related Report
      2016 Research-status Report
  • [Presentation] Development of N-sulfanyltehylanilide (SEAlide)-based traceable linker for enrichment and selective labeling of target proteins2016

    • Author(s)
      森崎巧也、傳田将也、山本 純、辻 大輔、猪熊 翼、伊藤孝司、重永 章、大高 章
    • Organizer
      第53回ペプチド討論会
    • Place of Presentation
      京都テルサ(京都府京都市)
    • Year and Date
      2016-10-26
    • Related Report
      2016 Research-status Report
  • [Presentation] One-pot sequential native chemical ligations using photocaged crypto-thioester2016

    • Author(s)
      山岡浩輔、粟飯原圭佑、成瀬公人、猪熊 翼、重永 章、大高 章
    • Organizer
      第53回ペプチド討論会
    • Place of Presentation
      京都テルサ(京都府京都市)
    • Year and Date
      2016-10-26
    • Related Report
      2016 Research-status Report
  • [Presentation] One-Pot/Sequential Native Chemical Ligation Using Photo-responsive Crypto-thioester2016

    • Author(s)
      粟飯原圭佑、山岡浩輔、成瀬公人、猪熊 翼、重永 章、大高 章
    • Organizer
      34th European Peptide Symposium 2016 & 8th International Peptide Symposium
    • Place of Presentation
      Leipzig (German)
    • Year and Date
      2016-09-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Intein-inspired Amide Bond Processing Device2016

    • Author(s)
      小宮千明、粟飯原圭佑、猪熊 翼、重永 章、大高 章
    • Organizer
      34th European Peptide Symposium 2016 & 8th International Peptide Symposium
    • Place of Presentation
      Leipzig (German)
    • Year and Date
      2016-09-04
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] 光応答型チオエステル等価体を用いた多成分One-pot NCL法の開発研究2016

    • Author(s)
      山岡浩輔、粟飯原圭佑、成瀬公人、猪熊 翼、重永 章、大高 章
    • Organizer
      創薬懇話会2016 in 蓼科
    • Place of Presentation
      エクシブ蓼科(長野県茅野市)
    • Year and Date
      2016-06-30
    • Related Report
      2016 Research-status Report
  • [Presentation] 標的タンパク質精製ツール“SEAlide-based traceable linker”の開発2016

    • Author(s)
      森崎巧也、傳田将也、辻 大輔、山本 純、猪熊 翼、伊藤孝司、重永 章、大高 章
    • Organizer
      日本ケミカルバイオロジー学会第11回年会
    • Place of Presentation
      京都テルサ(京都府京都市)
    • Year and Date
      2016-06-15
    • Related Report
      2016 Research-status Report
  • [Presentation] “SEAL-tag”を基盤とした細胞内での標的タンパク質ラベル化法の開発2016

    • Author(s)
      古曳泰規、傳田将也、森崎巧也、辻 大輔、猪熊 翼、伊藤孝司、重永 章、大高 章
    • Organizer
      日本ケミカルバイオロジー学会第11回年会
    • Place of Presentation
      京都テルサ(京都府京都市)
    • Year and Date
      2016-06-15
    • Related Report
      2016 Research-status Report
  • [Presentation] ペプチド化学を基盤としたケミカルバイオロジー研究のための基盤技術の開拓2016

    • Author(s)
      重永 章、大高 章
    • Organizer
      日本薬学会第136年会(シンポジウム「疾患代謝」から解明される生命現象と創薬研究への応用)
    • Place of Presentation
      パシフィコ横浜(神奈川県横浜市)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] N-Sアシル基転移反応を基盤としたタンパク質完全化学合成法の開拓2016

    • Author(s)
      重永 章
    • Organizer
      有機合成化学協会中国四国支部主催第74回パネル討論会『次世代を切り拓く全合成研究の若い力』
    • Place of Presentation
      徳島大学(徳島県徳島市)
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ペプチド化学を基盤としたケミカルバイオロジー研究のための基盤技術の開拓2015

    • Author(s)
      重永 章
    • Organizer
      名古屋大学大学院生命農学研究科食品機能化学特別セミナー
    • Place of Presentation
      名古屋大学(愛知県名古屋市)
    • Year and Date
      2015-10-16
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] タンパク質自己編集システムを範としたアミド結合切断反応の開発2015

    • Author(s)
      小宮千明、粟飯原圭佑、猪熊 翼、重永 章、大高 章
    • Organizer
      第三十一回若手化学者のための化学道場
    • Place of Presentation
      淡路夢舞台国際会議場(兵庫県淡路市)
    • Year and Date
      2015-08-27
    • Related Report
      2015 Research-status Report
  • [Remarks] 徳島大学大学院医歯薬学研究部(薬学域)機能分子合成薬学分野

    • URL

      http://www.tokushima-u.ac.jp/ph/faculty/labo/otaka/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 徳島大学教育研究者総覧

    • URL

      http://pub2.db.tokushima-u.ac.jp/ERD/person/147108/profile-ja.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 研究室ウェブサイト

    • URL

      http://www.tokushima-u.ac.jp/ph/faculty/labo/otaka/

    • Related Report
      2016 Research-status Report 2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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