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Synthesis of ss-glucan oligosaccharides and their biological evaluation

Research Project

Project/Area Number 20550149
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemistry related to living body
Research InstitutionTokyo Institute of Technology

Principal Investigator

TANAKA Hiroshi  Tokyo Institute of Technology, 大学院・理工学研究科, 准教授 (40334544)

Co-Investigator(Renkei-kenkyūsha) OHNO Naohito  東京薬科大学, 薬学部, 教授 (80152213)
Project Period (FY) 2008 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2008: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords自然免疫 / デクチン-1 / オリゴ糖 / グリコシル化反応 / 糖質 / グリコシル化 / デクチン1 / βグルカン / 多糖 / 免疫 / 固相合成
Research Abstract

In this report, we describe the synthesis and biological evaluation of β (1,3) oligosaccharides possessing an aminoalkyl group and their biological evaluation. A 2,3 diol glycoside with a 4,6 benziliden protecting group finctioned as an effective glycosyl acceptor for the synthesis ofβ ・1,3)linked glycosides. Using a combination of a linear tetrasaccharide and a branched pentasaccharide as glycosyl donors permitted β ・1,3)linear octa-to hexadecasaccharides and branched nona- to heptadecasaccharides to be prepared in good total yields. Measurements of the competitive effects of oligosaccharides on the binding of a soluble dectin-1 to a solid-supported Schizophyllan (SPG) revealed that the branched heptadecasacccharide and the linear hexadecasacccharides 2 also have binding activity for to dectine-1. In addition, the two oligosaccharides exhibited agonist activity in a luciferase-assisted NF-kB assay. This represents the first demonstration of a purely synthetic oligosaccahrides stimulating immunity mediated by dectin-1.

Report

(4 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • 2008 Annual Research Report
  • Research Products

    (17 results)

All 2010 2009 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (11 results) Book (3 results) Remarks (1 results)

  • [Journal Article] β(1,3)Branched Heptadeca-and Linear Hexadeca-saccharides Possessing an Aminoalkyl Group as a Strong Ligand to Dectin-12010

    • Author(s)
      田中浩士、河合徹也、安達禎之、大野尚仁、高橋孝志
    • Journal Title

      Cbem.Commun 42

      Pages: 5942-5944

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] β(1, 3) Branched Heptadeca-and Linear Hexadeca-saccharides Possessing an Aminoalkyl Group as a Strong Ligand to Dectin-12010

    • Author(s)
      H.Tanaka, et al
    • Journal Title

      Chemical Communications

      Volume: 42 Pages: 5942-5944

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] Synthesis of biologically important oligosaccharides and their applications to chemical biology research2010

    • Author(s)
      田中浩士
    • Organizer
      2nd ACGG Asian Communications of Glycobiology and Glycochemistry
    • Place of Presentation
      台北 台湾
    • Year and Date
      2010-10-29
    • Related Report
      2010 Annual Research Report
  • [Presentation] Efficient Synthesis of β(1,3) Oligosaccharides Exhibiting Dectin-1Agonist Activity.2010

    • Author(s)
      田中浩士、河合徹也、安達禎之、大野尚仁、高橋孝志
    • Organizer
      International Chemical Congress of Pacific Basin Society PACIFICHEM 2010
    • Place of Presentation
      Honolulu, Hawaii,USA
    • Related Report
      2010 Final Research Report
  • [Presentation] 自然免疫活性化作用を有するβグルカン誘導体の合成研究2010

    • Author(s)
      河合徹也、田中浩士、安達禎之、大野尚仁、高橋孝志
    • Organizer
      第98同有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2010 Final Research Report
  • [Presentation] 自然免疫活性化作用を有するβグルカン誘導体の合成研究2010

    • Author(s)
      河合徹也、田中浩士、安達禎之、大野尚仁、高橋孝志
    • Organizer
      第98回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis of biologically important oligosaccharides and their applications to chemical biology research2010

    • Author(s)
      田中浩士
    • Organizer
      2nd ACGG Asian Communications of Glycobiology and Glycochemistry
    • Place of Presentation
      Taipei(Invited lecuture)
    • Related Report
      2010 Final Research Report
  • [Presentation] 生物学上重要な糖鎖の効率的合成法の開発とケミカルバイオロジー研究への展開2010

    • Author(s)
      田中浩士
    • Organizer
      第59回高分子討論会
    • Place of Presentation
      北海道大学(依頼講演)
    • Related Report
      2010 Final Research Report
  • [Presentation] β(1,3)グルカン多糖類の合成法の開発2010

    • Author(s)
      河合徹也、田中浩士、武内良太、安達禎之、大野尚仁、高橋孝志
    • Organizer
      第29回日本糖質学会年会
    • Place of Presentation
      飛騨、岐阜
    • Related Report
      2010 Final Research Report
  • [Presentation] Synthesis ofβGlucan Oligosaccharide Derivatives Activating Innate Immunity2010

    • Author(s)
      河合徹也、田中浩士、安達禎之、大野尚仁、高橋孝志
    • Organizer
      第25回国際糖質学会
    • Place of Presentation
      幕張メッセ国際会議場,千葉
    • Related Report
      2010 Final Research Report
  • [Presentation] 自然免疫活性化作用を有するβグルカン誘導体の合成研究2010

    • Author(s)
      河合徹也、田中浩士、安達禎之、大野尚仁、高橋孝志
    • Organizer
      第90回日本化学会年会
    • Place of Presentation
      近畿大学、大阪
    • Related Report
      2010 Final Research Report
  • [Presentation] β(1,3)グルカン多糖類の合成法の開発2009

    • Author(s)
      河合徹也、田中浩士, 他4名
    • Organizer
      第29回日本糖質学会
    • Place of Presentation
      飛騨・世界生活文化センター
    • Year and Date
      2009-09-11
    • Related Report
      2009 Annual Research Report
  • [Presentation] グルカン多糖類の合成法の開発2009

    • Author(s)
      河合 徹也, ほか
    • Organizer
      日本化学会第89春季年会(2009)
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Book] βグルカンの基礎と応用-感染,抗がん,ならびに機能性食品へのβグルカンの関与-(精密有機合成技術とコンビナトリアル化学を基盤としたβグルカン関連糖鎖の合成)(大野尚人監修)2010

    • Author(s)
      田中浩士、高橋孝志
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Final Research Report
  • [Book] 複合糖質の化学と最新技術応用(ラボオートメーション技術を利用する効率的糖鎖合成法の開発研究)(正田晋一郎、稲津敏行監修)2010

    • Author(s)
      田中浩士、高橋孝志
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Final Research Report
  • [Book] βグルカンの基礎と応用 監修 大野尚人2010

    • Author(s)
      田中浩士, 高橋孝志
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.apc.titech.ac.jp/~ttakahas/index-j.html

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2008-04-01   Modified: 2016-04-21  

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