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Asymmetric construction of arylglycine unit and application to the synthesis of unnatural amino acid-containing peptide

Research Project

Project/Area Number 18K14869
Research Category

Grant-in-Aid for Early-Career Scientists

Allocation TypeMulti-year Fund
Review Section Basic Section 47010:Pharmaceutical chemistry and drug development sciences-related
Research InstitutionThe University of Tokushima

Principal Investigator

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) 2018-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2019: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywordsペプチド合成 / アリールグリシン / 不斉触媒 / アリール化 / イミン / 異常アミノ酸 / ペプチド / 不斉合成 / 非天然アミノ酸
Outline of Final Research Achievements

We previously developed a methodology for synthesis of non-canonical amino acid-containing peptide via direct asymmetric reaction to peptidic substrate. In this study, we planned to develop an asymmetric arylation to imino peptide for synthesis of peptide containing aryalglycine which is one of the non-canonical amino acid. As a result, although the substrate scope is somewhat narrow, we succeeded in developing an asymmetric arylation to model substrates in good yields and stereoselectivities.

Academic Significance and Societal Importance of the Research Achievements

ペプチドはそのアミノ酸配列に応じて多様な機能を付与できることから近年新たな医薬品候補化合物として注目されており、その構成成分を異常アミノ酸まで拡張すれば構造多様性が大きく拡充され新規医薬品創出の可能性が飛躍的に向上する。代表者が考案したペプチドへの直接的不斉反応は、不斉反応時の求核剤を変更するのみで多様な側鎖構造の異常アミノ酸をペプチド鎖に迅速に導入できる。そのため、本合成プロセスの反応適用拡大は異常アミノ酸含有ペプチドを基盤とする創薬研究を推し進める大きな駆動力となる。

Report

(3 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Research-status Report
  • Research Products

    (14 results)

All 2020 2019 2018

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Open Access: 3 results) Presentation (9 results) (of which Int'l Joint Research: 1 results,  Invited: 2 results)

  • [Journal Article] Development of a 1,3a,6a-Triazapentalene Derivative as a Compact and Thiol-specific Fluorescent Labeling Reagent2020

    • Author(s)
      Atsushi Nakayama, Akira Otani, Tsubasa Inokuma, Daisuke Tsuji, Haruka Mukaiyama, Akira Nakayama, Kohji Itoh, Akira Otaka, Keiji Tanino, and Kosuke Namba
    • Journal Title

      Communications Chemistry

      Volume: 3 Issue: 1 Pages: 1-9

    • DOI

      10.1038/s42004-019-0250-0

    • NAID

      120006877882

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Asymmetric Synthesis of α-Amino Phosphonic Acids Using Stable Imino Phosphonate as a Universal Precursor.2019

    • Author(s)
      Inokuma, T.; Sakakibara, T.; Someno, T.; Masui, K.; Shigenaga, A.; Otaka, A.; Yamada, K.
    • Journal Title

      Chem. Eur. J.

      Volume: 25 Issue: 60 Pages: 13829-13832

    • DOI

      10.1002/chem.201903572

    • NAID

      120006886354

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Optical resolution via catalytic generation of chiral auxiliary2019

    • Author(s)
      Kiyama Hiroki、Inokuma Tsubasa、Kuroda Yusuke、Yamaoka Yousuke、Takasu Kiyosei、Yamada Ken-ichi
    • Journal Title

      Tetrahedron Letters

      Volume: 60 Issue: 2 Pages: 175-177

    • DOI

      10.1016/j.tetlet.2018.12.006

    • NAID

      120006937697

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Unnatural Amino Acid-containing Peptides <i>via</i> Direct Asymmetric Reaction of Peptidyl Compounds2018

    • Author(s)
      猪熊 翼
    • Journal Title

      YAKUGAKU ZASSHI

      Volume: 138 Issue: 11 Pages: 1371-1379

    • DOI

      10.1248/yakushi.18-00143

    • NAID

      130007502978

    • ISSN
      0031-6903, 1347-5231
    • Year and Date
      2018-11-01
    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Journal Article] A Recyclable Hydrophobic Anchor-Tagged Asymmetric Amino Thiourea Catalyst2018

    • Author(s)
      Jichu Takahisa、Inokuma Tsubasa、Aihara Keisuke、Kohiki Taiki、Nishida Kodai、Shigenaga Akira、Yamada Ken-ichi、Otaka Akira
    • Journal Title

      ChemCatChem

      Volume: 10 Issue: 16 Pages: 3402-3405

    • DOI

      10.1002/cctc.201800714

    • NAID

      120006652009

    • Related Report
      2018 Research-status Report
    • Peer Reviewed / Open Access
  • [Presentation] 創薬テンプレート構築を指向した異常アミノ酸およびそれを含有するペプチドの合成法開発2020

    • Author(s)
      猪熊 翼
    • Organizer
      日本薬学会第140年会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] ペプチドへの直接的不斉反応による異常アミノ酸含有ペプチド新規合成法の開発2019

    • Author(s)
      猪熊 翼、増井 香奈、西田 航大、重永 章、大髙 章、山田 健一
    • Organizer
      日本ケミカルバイオロジー学会第14回年会
    • Related Report
      2019 Annual Research Report
  • [Presentation] Development of the direct asymmetric indolylation of imino peptide for synthesis of indolyl-glycine containing peptide2019

    • Author(s)
      Tsubasa Inokuma, Kana Masui, Kodai Nishida, Akira Shigenaga, Akira Otaka, Ken-ichi Yamada
    • Organizer
      第56回ペプチド討論会
    • Related Report
      2019 Annual Research Report
  • [Presentation] アリールグリシン含有ペプチドの効率的合成を指向したイミンへの不斉アリール化の検討2019

    • Author(s)
      猪熊 翼、染野 貴俊、山田 健一
    • Organizer
      第45回反応と合成の進歩シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] Chiral phosphoric acid-catalyzed asymmetric Mannich-type reaction using imino peptide as substrate2019

    • Author(s)
      Tsubasa Inokuma, Kodai Nishida, Kana Masui, Akira Shigenaga, Akira Otaka, Ken-ichi Yamada
    • Organizer
      第12回有機触媒シンポジウム
    • Related Report
      2019 Annual Research Report
  • [Presentation] ペプチドへの直接的不斉反応による異常アミノ酸含有ペプチド合成法の開発2019

    • Author(s)
      猪熊 翼
    • Organizer
      大阪大学蛋白研究所セミナー「30代研究者が切り拓くタンパク質化学合成の新潮流」
    • Related Report
      2018 Research-status Report
    • Invited
  • [Presentation] ペプチドへの直接的不斉反応によるインドリルグリシン含有ペプチドの合成2019

    • Author(s)
      猪熊 翼、西田 航大、重永 章、大髙 章、山田 健一
    • Organizer
      日本薬学会第139年会(千葉)
    • Related Report
      2018 Research-status Report
  • [Presentation] ペプチドイミンへの不斉1,2-付加を基盤とした非天然アミノ酸含有ペプチドの不斉合成2018

    • Author(s)
      猪熊 翼、岡田 和貴、西田 航大、重永 章、大高 章、山田 健一
    • Organizer
      第44回反応と合成の進歩シンポジウム
    • Related Report
      2018 Research-status Report
  • [Presentation] Novel methodology for the synthesis of a-indolyl-glycine containing peptide via direct asymmetric Friedel-Crafts reaction to peptidyl imine2018

    • Author(s)
      Tsubasa Inokuma, Kodai Nishida, Akira Shigenaga, Ken-ichi Yamada, Akira Otaka
    • Organizer
      The 35th European Peptide Symposium
    • Related Report
      2018 Research-status Report
    • Int'l Joint Research

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Published: 2018-04-23   Modified: 2021-02-19  

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