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Selective Chemical Trasformation of Specific Sugars for Diversification of Glycan Mediating Membrane Dynamics

Planned Research

Project AreaRegulation of membrane dynamics by glycan chemical knock-in
Project/Area Number 21H05078
Research Category

Grant-in-Aid for Transformative Research Areas (B)

Allocation TypeSingle-year Grants
Review Section Transformative Research Areas, Section (II)
Research InstitutionNational Institute of Advanced Industrial Science and Technology (2022-2023)
Kyoto University (2021)

Principal Investigator

Ueda Yoshihiro  国立研究開発法人産業技術総合研究所, 材料・化学領域, 主任研究員 (90751959)

Project Period (FY) 2021-08-23 – 2024-03-31
Project Status Completed (Fiscal Year 2023)
Budget Amount *help
¥18,590,000 (Direct Cost: ¥14,300,000、Indirect Cost: ¥4,290,000)
Fiscal Year 2023: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Fiscal Year 2022: ¥7,280,000 (Direct Cost: ¥5,600,000、Indirect Cost: ¥1,680,000)
Fiscal Year 2021: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Keywords糖 / 化学変換 / 位置選択性 / 機能制御 / アシル化 / シリル化 / ケージング / 臭素化 / ロタキサン / ライブラリ / 多様化 / ケージド糖
Outline of Research at the Start

糖類は細胞間コミュニケーション等において分子認識に関与し、多様な生命現象に関わっている。本研究では、申請者がこれまで独自に開発した触媒的位置選択的反応の知見を基盤に、様々な糖共存下で特定の糖選択的化学変換法を開発する。これによって酵素でも実現不可能な人工糖修飾法を提示し、領域目標である糖タンパクの膜動態の解析や人為制御に向けた糖鎖ケミカルノックイン研究を推進する。

Outline of Final Research Achievements

Precise synthesis of well-defined sugar derivatives is necessary to understand and control biological phenomena involving carbohydrates. In this study, we worked on the development of a method for selective chemical modification of a particular site on sugars. During the course of the study, a method for catalytic selective acylation of glucose derivatives was developed. In addition to acylation, we have discovered site-selective silylation of glucose derivatives and substrate-selective silylation of amino alcohols. By applying the developed selective functional group transformation method to the caging of bioactive sugars, we were able to develop a method to control sugar functions on the cell surface through collaborative research.

Academic Significance and Societal Importance of the Research Achievements

糖はアミノ酸と並び生体高分子の主要な構成成分であり、広範な生体内反応に関わっている。糖が関与する生命現象を理解し制御するためには、化学的に純粋な糖関連物質の精密合成が必要となるが、糖は分子内に複数の水酸基を有するため、合成や修飾には煩雑な保護/脱保護工程が必要であった。本研究では保護基を利用しない方法論の発展を目指し数種の新規選択的反応開発を行うことができた。独自の選択的反応をツールとして活用することで新しい生命科学研究にも展開することができ、合成化学から生命科学に波及効果をもたらす成果を挙げることができた。

Report

(4 results)
  • 2023 Annual Research Report   Final Research Report ( PDF )
  • 2022 Annual Research Report
  • 2021 Annual Research Report
  • Research Products

    (20 results)

All 2023 2022 2021

All Journal Article (6 results) (of which Int'l Joint Research: 2 results,  Peer Reviewed: 6 results,  Open Access: 1 results) Presentation (14 results) (of which Int'l Joint Research: 4 results,  Invited: 2 results)

  • [Journal Article] Practical Antibody Recruiting by Metabolic Labeling with Caged Glycans2023

    • Author(s)
      Milawati Hersa、Manabe Yoshiyuki、Matsumoto Takuya、Tsutsui Masato、Ueda Yoshihiro、Miura Ayane、Kabayama Kazuya、Fukase Koichi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 25

    • DOI

      10.1002/anie.202303750

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Journal Article] Rotaxane Synthesis by an End‐Capping Strategy via Swelling Axle‐Phenols2023

    • Author(s)
      Fujimura Koki、Ueda Yoshihiro、Yamaoka Yousuke、Takasu Kiyosei、Kawabata Takeo
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 30

    • DOI

      10.1002/anie.202303078

    • Related Report
      2023 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Structural Determination and Chemical Synthesis of the <i>N</i> ‐Glycan from the Hyperthermophilic Archaeon <i>Thermococcus kodakarensis</i>2023

    • Author(s)
      Hirao Kohtaro、Speciale Immacolata、Notaro Anna、Manabe Yoshiyuki、Teramoto Yoshiaki、Sato Takaaki、Atomi Haruyuki、Molinaro Antonio、Ueda Yoshihiro、De Castro Cristina、Fukase Koichi
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 62 Issue: 13

    • DOI

      10.1002/anie.202218655

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Approach toward Reversal of Chemoselectivity in Catalytic Silylation of Pyranosides2022

    • Author(s)
      Hashimoto, H.; Ueda. Y.; Fujimura, K.; Takasu, K.; Kawabata, T.
    • Journal Title

      Eur. J. Org. Chem.

      Volume: - Issue: 37

    • DOI

      10.1002/ejoc.202200949

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Organocatalytic Regio- and Enantioselective Vinylogous aza-Morita-Baylis-Hillman Reaction2022

    • Author(s)
      Gondo N.; , Koki K.; Hyakutake R.; Ueda Y.; Kawabata T.
    • Journal Title

      Tetrahedron Lett.

      Volume: 115 Pages: 154306-154306

    • DOI

      10.1016/j.tetlet.2022.154306

    • Related Report
      2022 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Substrate‐Selective Silylation of Primary Alcohols via Remote Functional‐Group Discrimination2022

    • Author(s)
      Hashimoto Hisashi、Ueda Yoshihiro、Takasu Kiyosei、Kawabata Takeo
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 61 Issue: 18

    • DOI

      10.1002/anie.202114118

    • Related Report
      2021 Annual Research Report
    • Peer Reviewed
  • [Presentation] 軸成分フェノールの触媒的臭素化によるロタキサン合成2023

    • Author(s)
      藤村光揮, 上田善弘, 山岡庸介, 高須清誠, 川端猛夫
    • Organizer
      第20回ホスト-ゲスト・超分子化学シンポジウム
    • Related Report
      2023 Annual Research Report
  • [Presentation] 水酸基識別型分子変換2023

    • Author(s)
      上田善弘
    • Organizer
      第56回天然物化学談話会
    • Related Report
      2023 Annual Research Report
    • Invited
  • [Presentation] 軸成分の触媒的臭素化によるロタキサンエンドキャップ形成2023

    • Author(s)
      藤村 光揮, 上田 善弘, 山岡 庸介, 高須 清誠, 川端 猛夫
    • Organizer
      第52回複素環化学討論会
    • Related Report
      2023 Annual Research Report
  • [Presentation] Rotaxane Synthesis by Catalytic Bromination of Axle Phenols2023

    • Author(s)
      Koki Fujimura, Yoshihiro Ueda, Yusuke Yamaoka, Kiyoshi Takasu, Takeo Kawabata
    • Organizer
      The 15th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-15)
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Brominative Rotaxane Synthesis for Derivatizable and Degradable Rotaxane2023

    • Author(s)
      Yoshihiro Ueda, Koki Fujimura, Kiyoshi Takasu, Takeo Kawabata
    • Organizer
      MRM2023/IUMRS-ICA2023
    • Related Report
      2023 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Seven-Step Stereodivergent Total Syntheses of Punicafolin and Macaranganin2022

    • Author(s)
      Yoshihiro Ueda, Hiromitsu Shibayama, Takeo Kawabata
    • Organizer
      The 15th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Related Report
      2022 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 構造の類似した第一級アルコールの触媒的基質選択的シリル化2022

    • Author(s)
      上田 善弘, 橋本 悠, 高須 清誠, 川端 猛夫
    • Organizer
      第64回天然有機化合物討論会
    • Related Report
      2022 Annual Research Report
  • [Presentation] 軸成分ハロゲン化によるロタキサン合成法の開発2022

    • Author(s)
      藤村光揮, 上田善弘, 山岡庸介, 高須清誠, 川端猛夫
    • Organizer
      第48回反応と合成の進歩シンポジウム
    • Related Report
      2022 Annual Research Report
  • [Presentation] 擬ロタキサンの芳香族ハロゲン化によるロタキサン合成2022

    • Author(s)
      藤村光揮, 上田善弘, 山岡庸介, 高須清誠, 川端猛夫
    • Organizer
      第15回有機触媒シンポジウム
    • Related Report
      2022 Annual Research Report
  • [Presentation] 遠隔位官能基認識に基づく第一級アルコールの触媒的基質選択的シリル化2022

    • Author(s)
      上田善弘、橋本悠、高須清誠、川端猛夫
    • Organizer
      日本薬学会第142年会
    • Related Report
      2021 Annual Research Report
  • [Presentation] 糖鎖ライブラリ多様化に向けた特定の糖選択的化学変換2022

    • Author(s)
      上田善弘
    • Organizer
      超異分野学会 東京大会2022
    • Related Report
      2021 Annual Research Report
  • [Presentation] 位置選択的官能基化を基盤とした糖関連天然物の合成2022

    • Author(s)
      上田善弘
    • Organizer
      第24回ケムステVシンポ「次世代有機触媒」
    • Related Report
      2021 Annual Research Report
    • Invited
  • [Presentation] Catalytic Silylative Discrimination of Primary Alcohols via Remote Functional Group Recognition2021

    • Author(s)
      Yoshihiro Ueda, Hisashi Hashimoto, Takeo Kawabata
    • Organizer
      13th AFMC International Medicinal Chemistry Symposium (AIMECS 2021)
    • Related Report
      2021 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 官能基間距離識別シリル化による長鎖ジオールの触媒的遠隔位不斉非対称化2021

    • Author(s)
      橋本悠、吉田圭佑、今吉亜由美、森崎一宏、上田善弘、川端猛夫
    • Organizer
      第119回有機合成シンポジウム
    • Related Report
      2021 Annual Research Report

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Published: 2021-10-22   Modified: 2025-01-30  

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