• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to previous page

Highly Efficient Synthesis of ADP-Ribosylated Peptides by Protecting Group Free Segment Coupling Methods

Research Project

Project/Area Number 18K05461
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 38040:Bioorganic chemistry-related
Research InstitutionGifu University

Principal Investigator

Tanaka Hidenori  岐阜大学, 糖鎖生命コア研究所, 助教 (20725064)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2018: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
KeywordsADPリボース / 無保護合成 / ピロリン酸 / ADPリボシル化アミノ酸 / ADPリボシル化ペプチド / N-グリコシド化 / ADPリボシル化ペプチド / ADPリボース / ピロリン酸結合形成 / N-グリコシド / ADPリボシル化 / 化学合成 / 無保護 / N-グリコシド
Outline of Final Research Achievements

ADP ribosylation, one of post-translational modifications, is a reaction that transfers ADP ribose from nicotinamide adenine dinucleotide (NAD+) to proteins and plays an important role in a variety of cellular processes including DNA repair and transcriptional regulation. Its biological importance has widely been investigated but detailed functions of ADP ribosylation remain poorly understood. The main difficulty in the molecular level research is to obtain homogeneous ADP ribosylated molecules. In this study, we develop a highly efficient method for synthesis of ADP ribosyl molecules. We established protecting-free pyrophosphate formation by phosphate cross-coupling reaction and applied it to chemical synthesis of mono- and di-ADP riboses.

Academic Significance and Societal Importance of the Research Achievements

ADPリボシル化の分子レベル機能解明研究のボトルネックは、構造均一な分子の量的供給であった。本研究では、リン酸クロスカップリング反応でピロリン酸結合を効率的に形成できることを実証し、ADPリボシル化分子の高効率合成法の開発の糸口を見出した。合成基盤の確立は分子の量的供給が可能とするため、ADPリボシル化の機能だけでなく、生物学的意義の解明に今後大きく貢献することが期待できる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (9 results)

All 2021 2020 2019

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (4 results)

  • [Journal Article] Stereoselective Synthesis of Diglycosyl Diacylglycerols with Glycosyl Donors Bearing a β-Stereodirecting 2,3-Naphthalenedimethyl Protecting Group2020

    • Author(s)
      Yagami Nahoko、Vibhute Amol M.、Tanaka Hide-Nori、Komura Naoko、Imamura Akihiro、Ishida Hideharu、Ando Hiromune
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 24 Pages: 16166-16181

    • DOI

      10.1021/acs.joc.0c02121

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Systematic strategy utilizing 1,5-lactamization for the synthesis of the trisialylated galactose unit of c-series gangliosides2020

    • Author(s)
      Shirasaki Junya、Tanaka Hide-Nori、Konishi Miku、Hirose Yuya、Imamura Akihiro、Ishida Hideharu、Kiso Makoto、Ando Hiromune
    • Journal Title

      Tetrahedron Letters

      Volume: 61 Issue: 16 Pages: 151759-151759

    • DOI

      10.1016/j.tetlet.2020.151759

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Sialyl Inositol Phosphosphingolipids CJP-2, CJP-3, and CJP-4 Isolated from Feather Star Comanthus japonica2019

    • Author(s)
      Goto Kenta、Tamai Hideki、Takeda Yoh、Tanaka Hide-Nori、Mizuno Takashi、Imamura Akihiro、Ishida Hideharu、Kiso Makoto、Ando Hiromune
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 11 Pages: 4054-4057

    • DOI

      10.1021/acs.orglett.9b01229

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Constrained sialic acid donors enable selective synthesis of α-glycosides2019

    • Author(s)
      Komura Naoko、Kato Keiichi、Udagawa Taro、Asano Sachi、Tanaka Hide-Nori、Imamura Akihiro、Ishida Hideharu、Kiso Makoto、Ando Hiromune
    • Journal Title

      Science

      Volume: 364 Issue: 6441 Pages: 677-680

    • DOI

      10.1126/science.aaw4866

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] p-tert-Butyl Groups Improve the Utility of Aromatic Protecting Groups in Carbohydrate Synthesis2019

    • Author(s)
      Asano Sachi、Tanaka Hide-Nori、Imamura Akihiro、Ishida Hideharu、Ando Hiromune
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 11 Pages: 4197-4200

    • DOI

      10.1021/acs.orglett.9b01372

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Presentation] リン酸クロスカップリング反応を鍵としたADPリボースclickable分子の高効率合成2021

    • Author(s)
      萩野瑠衣、河村奈緒子、安藤弘宗、田中秀則
    • Organizer
      2021年度日本農芸化学会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ポリADPリボース分岐構造の合成研究2021

    • Author(s)
      茂崎恵太、萩野瑠衣、河村奈緒子、安藤弘宗、田中秀則
    • Organizer
      2021年度日本農芸化学会
    • Related Report
      2020 Annual Research Report
  • [Presentation] 2位N-イミドイル保護グルコース供与体を用いた高β選択的グリコシル化反応2021

    • Author(s)
      淺野剛志、宇田川太郎、河村奈緒子、安藤弘宗、田中秀則
    • Organizer
      2021年度日本農芸化学会
    • Related Report
      2020 Annual Research Report
  • [Presentation] ポリ ADPリボース合成に向けた実用的リボシルアデノシンユニット構築法の開発2020

    • Author(s)
      萩野瑠衣、茂崎恵太、石田秀治、安藤弘宗、 田中秀則
    • Organizer
      2020年度日本農芸化学会
    • Related Report
      2019 Research-status Report

URL: 

Published: 2018-04-23   Modified: 2022-01-27  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi