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Novel methodology for the synthesis of unnatural amino acid-containing peptide based on asymmetric construction of indolyl glycine

Research Project

Project/Area Number 16K18845
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

INOKUMA Tsubasa  徳島大学, 大学院医歯薬学研究部(薬学系), 助教 (40541272)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywords非天然アミノ酸 / インドリルグリシン / 有機触媒 / 不斉反応 / ペプチド合成 / 不斉触媒 / Friedel-Crafts反応 / 中分子 / 酸化反応 / 非天然アミノ酸含有ペプチド / 疎水性アンカー
Outline of Final Research Achievements

Peptides have recently gained much interest for the development of novel pharmaceutics because they possess varieties of biological activities depending on their amino acid sequences. However, there is a problem arising from poor proteolytic stability in living systems. One of the solutions to overcome this difficulty is installation of unnatural amino acid units into peptides. The present methodology to prepare such peptides relies on asymmetric construction of unnatural amino acid units and installation into peptide elongation process. But this methodology requires multi-step reactions before its application to peptide synthesis. In this research, a novel concept for preparation of such peptides, an asymmetric construction of unnatural amino acid units directly in a growing peptide chain, was developed. By applying this new methodology, I succeeded in synthesis of indolyl glycine-containing peptide.

Report

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

    (6 results)

All 2018 2017 2016

All Journal Article (2 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 2 results,  Open Access: 1 results,  Acknowledgement Compliant: 1 results) Presentation (4 results) (of which Invited: 1 results)

  • [Journal Article] Direct enantioselective indolylation of peptidyl imine for the synthesis of indolyl glycine-containing peptides2018

    • Author(s)
      Tsubasa Inokuma, Kodai Nishida, Akira Shigenaga, Ken-ichi Yamada, Akira Otaka
    • Journal Title

      Heterocycles

      Volume: ‐

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A convenient method for preparation of alpha-imino carboxylic acid derivatives and application to the asymmetric synthesis of unnatural alpha-amino acid derivative2017

    • Author(s)
      Tsubasa Inokuma, Takahisa Jichu, Kodai Nishida, Akira Shigenaga, Akira Otaka
    • Journal Title

      Chemical and Pharmaceutical Bulletin

      Volume: 印刷中

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] ペプチドへの直接的不斉反応を基盤とする新規非天然アミノ酸含有ペプチド合成テクノロジーの開発2017

    • Author(s)
      猪熊 翼、西田 航大、重永 章、大高 章
    • Organizer
      日本薬学会第137年会(仙台)
    • Place of Presentation
      仙台国際センター「(宮城県・仙台市)」
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] MnO2を用いたα-イミノカルボン酸誘導体の効率的合成法の開発2017

    • Author(s)
      寺中 孝久、西田 航大、猪熊 翼、重永 章、大高 章
    • Organizer
      日本薬学会第137年会(仙台)
    • Place of Presentation
      東北大学「(宮城県・仙台市)」
    • Year and Date
      2017-03-25
    • Related Report
      2016 Research-status Report
  • [Presentation] ペプチドへの直接的不斉反応を基盤とした非天然アミノ酸含有ペプチドの新規効率的不斉合成法開発2017

    • Author(s)
      猪熊 翼
    • Organizer
      第56回日本薬学会・日本薬剤師会・日本病院薬剤師会中国四国支部学術大会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 非天然アミノ酸含有ペプチドの新規効率的合成法の開発2016

    • Author(s)
      西田 航大、猪熊 翼、重永 章、大高 章
    • Organizer
      第55回日本薬学会・日本薬剤師会・日本病院薬剤師会 中国四国支部学術大会
    • Place of Presentation
      就実大学「(岡山県)・(岡山市)」
    • Year and Date
      2016-11-05
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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