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Redesign of the Petasis reaction aiming facile polymeric amino acid synthesis

Research Project

Project/Area Number 19K05578
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 35010:Polymer chemistry-related
Research InstitutionGunma University

Principal Investigator

Kakuchi Ryohei  群馬大学, 大学院理工学府, 助教 (00743816)

Project Period (FY) 2019-04-01 – 2022-03-31
Project Status Completed (Fiscal Year 2021)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2021: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2020: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2019: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords多成分連結反応 / 高分子反応 / アミノ酸 / 高分子合成 / Petasis反応
Outline of Research at the Start

双性α-アミノ酸自身を繰り返し単位とする高分子は、その特徴的な化学構造に由来する材料特性が期待される。しかしながら、その化学合成は困難を極めている。本研究では、芳香族ボロン酸、グリオキシル酸、アミン間のPetasis三成分連結反応(Petasis-3CR)が有用な解決手段となりうると着目した。以上を考慮し、本研究では1) 高分子合成を指向したPetasis-3CRの再設計ならびに2) 改良Petasis-3CRによる新規高分子合成の開拓を行う。

Outline of Final Research Achievements

In the research, we aimed at optimizing and re-designing the Petasis three-component reaction (Petasis-3CR). The original Petasis-3CR refers to the reaction between aromatic boronic acids, amines, and glyoxylic acids. This research focused on the feasible optimization of the Petasis-3CR so that its integration with polymer synthesis will be enabled. For this, we have employed protected boronic acids to bypass the synthetic limitations arising from the polymers bearing boronic acids. Building on the modification we achieved in this work, the Petasis-3CR is allowed to be integrated with polymer synthesis, thereby providing poly (α-amino acids).

Academic Significance and Societal Importance of the Research Achievements

本研究では、従来合成が困難であったポリ(α-アミノ酸)を多様性志向的に合成することを可能とした。ポリ(α-アミノ酸)はその化学構造から、例えばアンチファウリング材料や有機触媒といった様々な材料分野への展開が期待される。

Report

(4 results)
  • 2021 Annual Research Report   Final Research Report ( PDF )
  • 2020 Research-status Report
  • 2019 Research-status Report
  • Research Products

    (35 results)

All 2021 2020 2019 Other

All Int'l Joint Research (1 results) Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Open Access: 1 results) Presentation (26 results) (of which Int'l Joint Research: 7 results,  Invited: 8 results)

  • [Int'l Joint Research] Chung Yuan Christian大学(CYCU)/R&D center for Membrane Technology(台湾)

    • Related Report
      2019 Research-status Report
  • [Journal Article] Streamlined access to end-functionalized thermoresponsive polymers via a combination of bulk RAFT polymerization and quasi solvent-free Passerini three-component reaction2021

    • Author(s)
      Hirama Arisa、Chou Li-Chieh、Kakuchi Ryohei
    • Journal Title

      Polymer Journal

      Volume: 53 Issue: 11 Pages: 1175-1185

    • DOI

      10.1038/s41428-021-00504-z

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Polymers of lignin-sourced components as a facile chemical integrant for the Passerini three-component reaction2021

    • Author(s)
      Kakuchi Ryohei、Tsuji Ryota、Fukasawa Kota、Yamashita Shuhei、Omichi Masaaki、Seko Noriaki
    • Journal Title

      Polymer Journal

      Volume: 53 Issue: 4 Pages: 523-531

    • DOI

      10.1038/s41428-020-00448-w

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rational Optimization of the Petasis Three‐Component Reaction as a Feasible Elementary Reaction in Polymer Chemistry2020

    • Author(s)
      Takahashi Ryo、Kakuchi Ryohei
    • Journal Title

      Macromolecular Chemistry and Physics

      Volume: 222 Issue: 2 Pages: 2000347-2000347

    • DOI

      10.1002/macp.202000347

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Computer-Aided Design of Postpolymerization Modification Reaction Based on Aminolysis of α,α-Difluoroacetate Esters2020

    • Author(s)
      Kakuchi Ryohei、Fukasawa Kota、Kikuchi Moriya、Narumi Atsushi、Kawaguchi Seigou、Li Yao、Kim Hyung、Amii Hideki
    • Journal Title

      Macromolecules

      Volume: 54 Issue: 1 Pages: 364-372

    • DOI

      10.1021/acs.macromol.0c02078

    • Related Report
      2020 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] The Passerini three-component reaction of aldehyde end-functionalized polymers via RAFT polymerization using chain transfer agents featuring aldehyde2020

    • Author(s)
      Kakuchi Ryohei、Okura Yamato
    • Journal Title

      Polymer Journal

      Volume: 52 Issue: 9 Pages: 1057-1066

    • DOI

      10.1038/s41428-020-0368-z

    • NAID

      40022335668

    • Related Report
      2020 Research-status Report
    • Peer Reviewed
  • [Journal Article] Multicomponent-Reaction-Ready Biomass-Sourced Organic Hybrids Fabricated via the Surface Immobilization of Polymers with Lignin-Based Compounds2019

    • Author(s)
      Hamada Takashi、Yamashita Shuhei、Omichi Masaaki、Yoshimura Kimio、Ueki Yuji、Seko Noriaki、Kakuchi Ryohei
    • Journal Title

      ACS Sustainable Chemistry & Engineering

      Volume: 7 Issue: 8 Pages: 7795-7803

    • DOI

      10.1021/acssuschemeng.8b06812

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] The dawn of polymer chemistry based on multicomponent reactions2019

    • Author(s)
      Kakuchi Ryohei
    • Journal Title

      Polymer Journal

      Volume: 51 Issue: 10 Pages: 945-953

    • DOI

      10.1038/s41428-019-0209-0

    • NAID

      40022176626

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Surface Engineering of Fluoropolymer Films via the Attachment of Crown Ether Derivatives Based on the Combination of Radiation-Induced Graft Polymerization and the Kabachnik?Fields Reaction2019

    • Author(s)
      Omichi Masaaki、Yamashita Shuhei、Okura Yamato、Ikutomo Ryuta、Ueki Yuji、Seko Noriaki、Kakuchi Ryohei
    • Journal Title

      Polymers

      Volume: 11 Issue: 8 Pages: 1337-1337

    • DOI

      10.3390/polym11081337

    • Related Report
      2019 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] An engineered Petasis three-component reaction for the synthesis of poly(α-amino acid)2021

    • Author(s)
      Li Chieh Chou, Ryo Takahashi, and Ryohei Kakuchi
    • Organizer
      第70回高分子年次学会
    • Related Report
      2021 Annual Research Report
  • [Presentation] Petasis3成分連結反応の高分子合成を指向した改良2021

    • Author(s)
      周立杰、覚知亮平
    • Organizer
      第70回高分子討論会
    • Related Report
      2021 Annual Research Report
  • [Presentation] コンピューター化学による有機素反応の解析を通じた高分子合成反応の合理的設計2021

    • Author(s)
      覚知亮平, 深澤宏太, 網井秀樹
    • Organizer
      計算科学研究センター・ナノテクノロジープラットフォーム事業合同ワークショップ, オンライン
    • Related Report
      2020 Research-status Report
  • [Presentation] 高分子合成を指向した有機変換反応の選択ならびに最適化2021

    • Author(s)
      覚知亮平
    • Organizer
      第 3 回産学官連携交流会 (第 1 1 5 回複合材料懇話会), オンライン
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] Synthetic application of the Passerini three component reaction for the chain end modification of polymers end-functionalized with aldehyde groups2021

    • Author(s)
      Li-Chieh Chou, Arisa Hirama, and Ryohei Kakuchi
    • Organizer
      高分子学会北関東地区講演会, オンライン
    • Related Report
      2020 Research-status Report
  • [Presentation] Optimization of the Multi-Component Reaction for Application to Polymer Synthesis2020

    • Author(s)
      Ryo Takahashi,Ryohei Kakuchi
    • Organizer
      3rd G’L’owing Polymer Symposium in KANTO (GPS-K2020), Online
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [Presentation] Polymers containing Lignin derived unit for the efficient Passerini Three-Component Reaction2020

    • Author(s)
      Ryota Tsuji, Kota Fukasawa, Masaaki Omichi, and Noriaki Seko, and Ryohei Kakuchi
    • Organizer
      3rd G’L’owing Polymer Symposium in Kanto (GPS-K2020), 2020, Online
    • Related Report
      2020 Research-status Report
    • Int'l Joint Research
  • [Presentation] Friedel-Crafts重縮合によるジフルオロ酢酸エステル基含有ポリマーの合成ならびに反応性の評価2020

    • Author(s)
      深澤宏太, 網井秀樹,覚知亮平
    • Organizer
      第43回フッ素化学討論会
    • Related Report
      2020 Research-status Report
  • [Presentation] 多成分連結反応による高分子合成の新展開2020

    • Author(s)
      覚知亮平
    • Organizer
      第69回高分子学会年次大会
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] 高分子合成を指向した有機変換反応の選択・最適化2020

    • Author(s)
      覚知亮平, 深澤宏太, 網井秀樹
    • Organizer
      第69回高分子学会討論会, オンライン
    • Related Report
      2020 Research-status Report
  • [Presentation] 多成分連結反応による高分子反応を活用したアミノリン酸含有ポリマーの合成2020

    • Author(s)
      高橋良, 辻亮太, 覚知亮平
    • Organizer
      第69回高分子学会討論会, オンライン
    • Related Report
      2020 Research-status Report
  • [Presentation] 高分子合成における素反応の深化と天然由来物質を活用した材料創成2020

    • Author(s)
      覚知亮平
    • Organizer
      20-1 エコマテリアル研究会, オンライン
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] 多成分連結反応を素反応とする高分子合成ならびに繊維修飾への展開2020

    • Author(s)
      覚知亮平
    • Organizer
      繊維学会秋季研究発表会, オンライン
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] 新規高分子反応系の構築と芳香族系ポリマーの重合後修飾への展開2020

    • Author(s)
      覚知亮平
    • Organizer
      日本ポリイミド・芳香族系高分子会議
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] 高分子合成における新しい素反応の選択ならびに最適化2020

    • Author(s)
      覚知亮平
    • Organizer
      高分子学会東北支部講演会, オンライン
    • Related Report
      2020 Research-status Report
    • Invited
  • [Presentation] Multicomponent Reactions in Polymer Chemistry: From Synthetic Chemistry to Material Applications2019

    • Author(s)
      Ryohei Kakuchi
    • Organizer
      International Symposium on Polymer Synthesis and Materials
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Multiple Reactivity in Polymer Synthesis ~ From Fundamental Chemistry to Material Applications2019

    • Author(s)
      Ryohei Kakuchi
    • Organizer
      S-Membrane International Conference 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Synthesis and reactivity of difluoroacetate containing polymers2019

    • Author(s)
      Kota Fukasawa, Shuhei Yamashita, Hideki Amii, Ryohei Kakuchi
    • Organizer
      S-Membrane International Conference 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Highly Reactive Fabrics From Biomass Resources2019

    • Author(s)
      Shuhei Yamashita, Takashi Hamada, Masaaki Omichi, Kimio Yoshimura, Yuji Ueki, Noriaki Seko and Ryohei Kakuchi
    • Organizer
      S-Membrane International Conference 2019
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Multi-Component Reactions in Synthetic Polymer Chemistry; From Fundamental Chemistry to Material Applications2019

    • Author(s)
      Ryohei Kakuchi
    • Organizer
      FAPS 2019 Polymer Congress
    • Related Report
      2019 Research-status Report
    • Int'l Joint Research
  • [Presentation] Multicomponent post-polymerization modification reactions on biomass-sourced organic hybrids2019

    • Author(s)
      Ryohei Kakuchi, Shuhei Yamashita, Yamato Okura, Takashi Hamada, Masaaki Omichi, Yuji Ueki, and Noriaki Seko
    • Organizer
      第68回高分子年次大会
    • Related Report
      2019 Research-status Report
  • [Presentation] α,α-ジフルオロ酢酸エステル基含有ポリマーの合成及び反応性2019

    • Author(s)
      深澤宏太、山下修平、網井秀樹、覚知亮平
    • Organizer
      第68回高分子年次大会
    • Related Report
      2019 Research-status Report
  • [Presentation] Friedel-Crafts 重合による高分子への活性化エステル基の精密導入2019

    • Author(s)
      覚知亮平、深澤宏太、山下修平、網井秀樹
    • Organizer
      第68回高分子年次大会
    • Related Report
      2019 Research-status Report
  • [Presentation] バイオマス由来材料のみを出発原料とした放射線グラフト重合及び多成分連結反応による機能性ハイブリッド材料の合成2019

    • Author(s)
      山下 修平, 大道 正明, 植木 悠二, 瀬古 典明, 覚知 亮平
    • Organizer
      第68回高分子討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] ETFE膜表面へのクラウンエーテルの導入と色素吸着能の評価2019

    • Author(s)
      山下修平、大道正明、大倉大和、生友隆太、植木悠二、網井秀樹、瀬古典明、覚知亮平
    • Organizer
      第9回フッ素化学若手の会
    • Related Report
      2019 Research-status Report
  • [Presentation] α,α-ジフルオロ酢酸エステル基含有ポリマーの合成ならびに反応性の評価2019

    • Author(s)
      深澤宏太、山下修平、網井秀樹、覚知亮平
    • Organizer
      第9回フッ素化学若手の会
    • Related Report
      2019 Research-status Report

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Published: 2019-04-18   Modified: 2023-01-30  

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