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Development of high atom economy synthesis of cyclic peptides based on sequential amidation-cyclization

Research Project

Project/Area Number 15K17852
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Fuse Shinichiro  東京工業大学, 科学技術創成研究院, 准教授 (00505844)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords環状ペプチド / マイクロフロー合成 / 光反応 / NCA / マイクロフロー / 瞬間混合 / ペプチド / アミド化
Outline of Final Research Achievements

Aim of this research was development of peptide chain elongation using alpha-amino acid-N-carboxy anhydride and photochemical cyclization of peptides for efficient cyclic peptide synthesis. We successfully developend and reported photochemical cyclization of peptides in an academic journal. On the other hand, peptide chain elongation using alpha-aminoacid-N-carboxy anhydride was rather difficult. In the couse of our research, however, we developed new synthetic approach for alpha-aminoacid-N-carboxy anhydrides. It alllowed us to synthesize alpha-aminoacid-N-carboxy anhydride that could not be synthesized by previously reported synthetic approaches.

Report

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

    (36 results)

All 2018 2017 2016 2015 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Open Access: 2 results,  Acknowledgement Compliant: 2 results) Presentation (26 results) (of which Int'l Joint Research: 8 results,  Invited: 14 results) Book (3 results) Remarks (3 results)

  • [Journal Article] Recent Advances in the Integrated Micro-flow Synthesis Containing Photochemical Reactions2018

    • Author(s)
      Y. Otake, H. Nakamura, S. Fuse
    • Journal Title

      Tetrahedron Lett.

      Volume: 59 Issue: 18 Pages: 1691-1697

    • DOI

      10.1016/j.tetlet.2018.03.019

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Integrated Micro-flow Synthesis Based on Photochemical Wolff Rearrangement2018

    • Author(s)
      S. Fuse, Y. Otake, H. Nakamura
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2018 Issue: 44 Pages: 6466-6473

    • DOI

      10.1002/ejoc.201700789

    • NAID

      120006582622

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] A Rapid and Clean Synthetic Approach for Cyclic Peptides via Micro-flow Peptide Chain Elongation and Photochemical Cyclization: Synthesis of Cyclic RGD Peptide2016

    • Author(s)
      Yuto Mifune, Hiroyuki Nakamura, Shinichiro Fuse
    • Journal Title

      Organic and Biomolecular Chemistry

      Volume: 14 Issue: 47 Pages: 11244-11249

    • DOI

      10.1039/c6ob02391f

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation2016

    • Author(s)
      Shinichiro Fuse, Yuto Mifune, Hiroyuki Nakamura, Hiroshi Tanaka
    • Journal Title

      Nature Communications

      Volume: 7 Issue: 1 Pages: 1-7

    • DOI

      10.1038/ncomms13491

    • NAID

      120006582554

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] マイクロフローアミド結合形成法を駆動力とするペプチド合成の革新2018

    • Author(s)
      布施新一郎
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] マイクロフローリアクター内での瞬間pH転換に基づくN-カルボキシ無水物の高効率合成2018

    • Author(s)
      小竹佑磨、中村浩之、布施新一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor2018

    • Author(s)
      小竹佑磨、中村浩之、布施新一郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acid Flash Switching in a Micro-flow Reactor2018

    • Author(s)
      Y. Otake, H. Nakamura, S. Fuse
    • Organizer
      International CLS Forum 2018
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly Efficient Amide Bond Formation using Micro-flow Technology2018

    • Author(s)
      S. Fuse
    • Organizer
      Tokyo Tech-KAIST Joint Workshop
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor2018

    • Author(s)
      Y. Otake, H. Nakamura, S. Fuse
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis (ICAMS-1)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Highly Efficient Amide Bond Formation Using Micro‐flow Technology2018

    • Author(s)
      S. Fuse
    • Organizer
      The First International Conference on Automated Flow and Microreactor Synthesis (ICAMS-1)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] マイクロフロー法を駆使するペプチドの高効率合成2017

    • Author(s)
      布施新一郎
    • Organizer
      人・環境と物質をつなぐイノベーション創出ダイナミックアライアンス 2017年度生命機能 物質・デバイス・システムプロジェクトグループ(G3)分科会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Highly Efficient Amide Bond Formation Using Micro‐flow Technology2017

    • Author(s)
      S. Fuse
    • Organizer
      The 12th International Conference on Cutting-Edge Organic Chemistry in Asia / The 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 迅速かつ強力なカルボン酸の活性化を基盤とするマイクロフローペプチド合成法の開発2017

    • Author(s)
      布施新一郎、御舩悠人、小竹佑磨、高橋孝志、田中浩士、中村浩之
    • Organizer
      35回メディシナルケミストリーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] マイクロフローアミド化法を駆使するペプチドの高効率合成2017

    • Author(s)
      布施新一郎
    • Organizer
      化学とマイクロ・ナノシステム学会第36回研究会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 迅速かつ強力なカルボン酸の活性化を基盤とするマイクロフローペプチド合成法の開発2017

    • Author(s)
      布施新一郎
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ペプチドの低コスト生産を志向したマイクロフローアミド結合形成法の開発2017

    • Author(s)
      布施新一郎
    • Organizer
      第5回バイオ関連化学シンポジウム若手フォーラム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 微小流路中での高速アミド化反応(秒単位)を駆使するペプチド合成2017

    • Author(s)
      布施新一郎
    • Organizer
      第49回若手ペプチド夏の勉強会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] マイクロフロー法を駆使するペプチドの高効率合成2017

    • Author(s)
      布施新一郎
    • Organizer
      平成28年度附置研アライアンス成果報告会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Highly Efficient Amide Bond Formation Using Micro‐flow Technology2017

    • Author(s)
      S. Fuse
    • Organizer
      International Symposium on Pure & Applied Chemistry (ISPAC) 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] マイクロフロー法を駆使するN-メチル化ペプチドの効率的合成2017

    • Author(s)
      小竹佑磨、中村浩之、布施新一郎
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] マイクロフローペプチド合成法の開発-奥深いアミド化の世界-2017

    • Author(s)
      布施新一郎
    • Organizer
      東工大応用化学系次世代を担う若手シンポジウム
    • Place of Presentation
      東京工業大学
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] An efficient amide bond formation through rapid and strong activation of carboxylic acids in a micro-flow reactor2017

    • Author(s)
      Shinichiro Fuse
    • Organizer
      7th CCS-CSJ Young Chemists Forum 2017 -Frontier in Organic Synthesis toward Middle Molecular Strategy-
    • Place of Presentation
      Keio University
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] マイクロフローアミド化・光環化反応を駆使する高効率環状ペプチドの合成法の開発2017

    • Author(s)
      布施 新一郎、御舩 悠人、中村 浩之
    • Organizer
      日本化学会第97回年会
    • Place of Presentation
      慶應義塾大学
    • Related Report
      2016 Research-status Report
  • [Presentation] マイクロフローアミド結合形成法の開発 -単純なようで奥深いアミド化の世界-2016

    • Author(s)
      布施新一郎
    • Organizer
      第11回プロセス化学ラウンジ
    • Place of Presentation
      和光純薬工業株式会社湯河原研修所
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 強力かつ迅速なカルボン酸の活性化を基盤とするマイクロフローペプチド合成法の開発2016

    • Author(s)
      布施新一郎
    • Organizer
      2016年度第7回日本化学会反応工学部会マイクロ化学プロセス分科会主催講演会
    • Place of Presentation
      淀川製作所テクノロジー・イノベーションセンター
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] わずか5秒以内でアミノ酸を連結する超高速マイクロフローペプチド合成法の開発2016

    • Author(s)
      布施新一郎
    • Organizer
      第6回CSJ化学フェスタ2016
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] フロー反応でしか実現できない高効率合成法開発を目指して2016

    • Author(s)
      布施新一郎
    • Organizer
      電磁波励起反応場第188委員会 平成28年度 第1回化学材料分科会「マイクロ波化学・材料合成装置を学ぶ」
    • Place of Presentation
      東京工業大学
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] Utilization of microflow technology for the site-selective modification of multifunctionalized molecules2015

    • Author(s)
      Shinichiro Fuse , Yuto Mifune , Nobutake Tanabe , Hiroyuki Nakamura , Takashi Takahashi
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 生物活性天然物のマイクロフロー合成:「マイクロフロー法ならでは」の手法論開発を目指して2015

    • Author(s)
      布施新一郎
    • Organizer
      マイクロ化学生産研究コンソーシアム講演会および成果報告会
    • Place of Presentation
      京都大学 桂キャンパス
    • Year and Date
      2015-12-10
    • Related Report
      2015 Research-status Report
    • Invited
  • [Book] 中分子創薬に資するペプチド・核酸・糖鎖の合成技術2018

    • Author(s)
      布施新一郎
    • Total Pages
      10
    • Publisher
      シーエムシー出版
    • ISBN
      9784781313207
    • Related Report
      2017 Annual Research Report
  • [Book] DOJIN ACADEMIC SERIES現代光化学2018

    • Author(s)
      布施新一郎
    • Total Pages
      10
    • Publisher
      化学同人
    • Related Report
      2017 Annual Research Report
  • [Book] ペプチド医薬品開発のためのスクリーニング・安定化・製剤化技術2018

    • Author(s)
      布施新一郎
    • Total Pages
      6
    • Publisher
      技術情報協会
    • Related Report
      2017 Annual Research Report
  • [Remarks] 中村・布施研究室 研究紹介

    • URL

      http://syn.res.titech.ac.jp/research/

    • Related Report
      2017 Annual Research Report
  • [Remarks] 副反応を起こしやすいアミノ酸を迅速かつクリーンに連結―抗HIV抗菌ペプチドの大量生産に道―

    • URL

      http://www.titech.ac.jp/news/2016/036841.html

    • Related Report
      2016 Research-status Report
  • [Remarks] 布施新一郎准教授、御舩悠人大学院生、中村浩之教授らの研究成果に関する記事が『日経産業新聞』に掲載

    • URL

      http://www.iir.titech.ac.jp/2016/12/08/mediacoverage-21/

    • Related Report
      2016 Research-status Report

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

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