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Synthesis of chemical probes containing di/oligosialialic acids and their biological evaluation related to innate immunity

Research Project

Project/Area Number 26282209
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Biomolecular chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Tanaka Hiroshi  東京工業大学, 物質理工学院, 准教授 (40334544)

Co-Investigator(Kenkyū-buntansha) 佐藤 ちひろ  名古屋大学, 学内共同利用施設等, 准教授 (10343211)
Co-Investigator(Renkei-kenkyūsha) YAMAGUCHI Yoshiki  国立研究開発法人理化学研究所, 糖鎖構造生物学研究チーム, チームリーダー (90323451)
Project Period (FY) 2014-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥16,770,000 (Direct Cost: ¥12,900,000、Indirect Cost: ¥3,870,000)
Fiscal Year 2016: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2014: ¥6,110,000 (Direct Cost: ¥4,700,000、Indirect Cost: ¥1,410,000)
Keywords糖鎖 / シアル酸 / 免疫 / グリコシル化 / 高分子 / リビング重合 / ケミカルバイオロジー / 有機合成 / 自然免疫 / オリゴ糖 / ケミカルバイオロロジー / 免疫調整剤 / Siglecs / 重合反応 / Siglec-7
Outline of Final Research Achievements

In this report, we first investigated that partially unprotected sialyl donors underwent a-selective glycosidation without use of an acetonitrile effect. To demonstrate the utility of the method, a straight forward synthesis of α(2,9) disialosides containing N-acetyl and/or N-glycolyl groups was achieved by using the two N-acetyl and N-glycolyl sialyl donors. Next we successfully prepared Glycopolymers possessing disialic acids with a narrow with narrow polydisparities from glycosylated monomers via π-allyl nickel catalyzed coordinating polymerization. A biological evaluation of the glycopolymers and revealed that the synthetic fluoroecent-labelled glycopolymers cause the Siglec-7-GD3 interaction to dissociate in the micromolar concentration range. Finally we prepared the synthesis of dextran derivative possessing disialic acids via polymer reactions. The glycopolymer was able to release Siglec7 from Siglec7-GD3 complex possibly.

Report

(4 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • Research Products

    (19 results)

All 2017 2016 2015 2014 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (13 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results) Book (1 results) Remarks (2 results)

  • [Journal Article] Chemical synthesis and evaluation of a disialic acid-containing dextran polymer as an inhibitor of sialic acid binding immunoglobulin-like lectin, Siglec 72017

    • Author(s)
      Sho Yamaguchi, Atsushi Yoshimura, Yu Yasuda, Airi Mori, Hiroshi Tanaka, Takashi Takahashi, Ken Kitajima and Chihiro Sato
    • Journal Title

      ChemBioChem

      Volume: - Issue: 13 Pages: 1194-1203

    • DOI

      10.1002/cbic.201600694

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of end-functionalized glycopolymers containing α(2,8) disialic acids via π-allyl nickel catalyzed coordinating polymerization and their interaction with Siglec-72017

    • Author(s)
      Ohira, S.; Yasuda, Y.; Tomita, I.; Kitajima, K.; Takahashi, T.; Sato, C.; *Tanaka, H.
    • Journal Title

      Chem. Commun.

      Volume: 53 Issue: 3 Pages: 553-556

    • DOI

      10.1039/c6cc07115e

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Journal Article] The α-Glycosidation of Partially Unprotected N-Acetyl and N-Glycolyl Sialyl Donors in the Absence of a Nitrile Solvent Effect2016

    • Author(s)
      Taku Aoyagi, Shuichi Ohira, Shinichiro Fuse, Jun Uzawa, Yoshiki Yamaguchi, Hiroshi Tanaka
    • Journal Title

      Chemistry A Europian Jounal

      Volume: 22 Issue: 20 Pages: 6968-6973

    • DOI

      10.1002/chem.201601031

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 環状カーボネート保護基を有するシアル酸糖供与体を用いるα(2,8)オリゴシアル酸の合成研究2016

    • Author(s)
      鯉沼僚輔、青柳拓、田中浩士
    • Organizer
      第35回 日本糖質学会年会
    • Place of Presentation
      高知
    • Year and Date
      2016-09-01
    • Related Report
      2016 Annual Research Report
  • [Presentation] N-アセチル/グリコリル型シアル酸供与体を用いたα(2,9)ジシアル酸の合成と機能評価2016

    • Author(s)
      青柳 拓・五島 亜実・鵜澤 洵・大平 脩一・山口 芳樹・北島 健・佐藤 ちひろ・田中 浩士
    • Organizer
      日本化学会第96春季年会(2016)
    • Place of Presentation
      同志社大学 京田辺キャンパス
    • Year and Date
      2016-04-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Effects of N- and O-protecting groups of thiosialoside on their reactivity and stereo selectivity towards glycosidation2016

    • Author(s)
      Hiroshi Tanaka
    • Organizer
      Glycoretreat 2016
    • Place of Presentation
      台湾
    • Year and Date
      2016-04-11
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Effects of N- and O-protecting groups of thiosialoside on their reactivity and stereo selectivity towards glycosidation2016

    • Author(s)
      Hiroshi Tanaka
    • Organizer
      2016 Glycoretreat
    • Place of Presentation
      New Taipei City Taiwan
    • Year and Date
      2016-04-11
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Partially Unprotected N-Acetyl Sialyl Donors Undergoing α-Sialylation without the Nitrile Effect,2015

    • Author(s)
      Taku Aoyagi, Syuichi Ohira, Shinichiro Fuse, Hiroshi Tanaka.
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (Pacifichem 2015)
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 免疫細胞におけるSiglec-7の新規リガンド結合部位による免疫応答制御2015

    • Author(s)
      五島 亜実、山川 奈緒、安田 優、田中 浩士、宮田 真路、北島 健、佐藤 ちひろ
    • Organizer
      第38回分子生物学会年会、第88回日本生化学学会
    • Place of Presentation
      神戸ポートアイランド
    • Year and Date
      2015-12-01
    • Related Report
      2015 Annual Research Report
  • [Presentation] Development of new methodology for a-sialyaltion and Synthesis of glycopolymers from sialylated allene monomers.2015

    • Author(s)
      Hiroshi Tanaka
    • Organizer
      The 7th ACGG conference
    • Place of Presentation
      Matsushima, Miyagi, Japan
    • Year and Date
      2015-11-12
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 遊離水酸基を有するN-アセチルシアル酸供与体を用いたα選択的シアリル化反応2015

    • Author(s)
      青栁拓、大平脩一、鵜澤 洵、山口芳樹、田中浩士
    • Organizer
      GlycoTokyo2015
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Year and Date
      2015-10-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] 遊離水酸基を有する N - アセチルシアル酸供与体を用いる α 選択的シアリル化反応2015

    • Author(s)
      青柳拓, 大平脩一, 田中浩士
    • Organizer
      第34回日本糖質学会年会
    • Place of Presentation
      東京
    • Year and Date
      2015-07-31
    • Related Report
      2015 Annual Research Report
  • [Presentation] 遊離水酸基を有するN-アセチルシアル酸供与体を用いたα選択 的シアリル化反応2015

    • Author(s)
      青栁拓, 大平脩一, 布施新一 郎, 田中浩士
    • Organizer
      日本化学会第95回春季年会
    • Place of Presentation
      日本大学理工学部(千葉県・船橋市)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] α-Selective glycosidation of using N-acetyl sialyl donors possessing a free hydroxyl group at the C4 position2014

    • Author(s)
      Taku Aoyagi, Shuichi Ohira, Hiroshi Tanaka
    • Organizer
      Society for Glycobiology (SFG) & Japanese Society of Carbohydrate Research (JSCR) 2014 Joint Annual Meeting
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2014-11-16 – 2014-11-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] The Synthesis of Sialo-containing Glycopolymers by π-Allyl Nickel Catalyzed Coordination Polymerization.2014

    • Author(s)
      Shuichi Ohira, Yu Yasuda, Chihiro Sato, Ken KItajima, Ikuyoshi Tomita, Takashi Takahashi, Hiroshi Tanaka
    • Organizer
      Society for Glycobiology (SFG) & Japanese Society of Carbohydrate Research (JSCR) 2014 Joint Annual Meeting
    • Place of Presentation
      Hawaii, USA
    • Year and Date
      2014-11-16 – 2014-11-18
    • Related Report
      2014 Annual Research Report
  • [Presentation] 4 位遊離水酸基を有する N - アセチルシアル酸供与体を用いる α 選択的シアリル化反応2014

    • Author(s)
      青柳拓, 大平脩一, 布施新一郎, 田中浩士.
    • Organizer
      第33回日本糖質学会年会
    • Place of Presentation
      名古屋大学豊田講堂(愛知県・名古屋市)
    • Year and Date
      2014-08-10 – 2014-08-12
    • Related Report
      2014 Annual Research Report
  • [Book] Glycoscience: Biology and Medicine2014

    • Author(s)
      Hiroshi Tanaka
    • Total Pages
      6
    • Publisher
      Springer
    • Related Report
      2014 Annual Research Report
  • [Remarks] 田中(浩)研究室 東京工業大学

    • URL

      http://www.apc.titech.ac.jp/~htanaka/

    • Related Report
      2016 Annual Research Report
  • [Remarks]

    • URL

      http://www.apc.titech.ac.jp/~htanaka/index.html

    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-04-04   Modified: 2018-03-22  

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