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CONSTRUCTION OF NOBEL PLIERS-LIKES A CCHARIDE-RECEPTOR SENSORS USING THE RING FLIP OF XYLOSE

Research Project

Project/Area Number 17550151
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

YUASA Hideya  TOKYO INSTITUTE OF TECHNOLOGY, GRADUATE SCHOOL OF BIOSCIENCE AND BIOTECHNOLOGY, ASSOCIATE PROFESSOR, 大学院生命理工学研究科, 助教授 (90261156)

Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2006: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2005: ¥1,900,000 (Direct Cost: ¥1,900,000)
KeywordsMolecular Devices / Molecular Machines / Hinge Sugar / Functional Oligosaccharides / Biosensors / Fluorescent Sensors / Excimer Complex / Molecular Pliers / 超分子化学 / ナノバイオ / 合成化学 / オリゴ糖 / 生体分子 / 糖化学
Research Abstract

Some of bacteria infect human through the recognition of cell surface oligosaccharides. Thus the sensors detecting the oligosaccharide receptors are expected to be the diagnostic tools for the bacteria. We have succeeded in synthesizing a molecule that permit pliers-like motion and developed a metal ion sensor that gives excimer fluorescence on chelation to a metal ion through the closure of the molecular pliers. If we can attach two identical saccharides at the handles of the molecular pliers, this would permit chelation to two subsites of the recognition pocket of a saccharide receptor. This study aims at synthesizing a sensor for a relatively low-priced lectin to optimize the structural prerequisites to be a practical lectin sensor. We attached pyrenyl and naphthyl groups at 2,4-positons and two mannose residues at 1,3-positions of xylose through alkyl chain spacers. Although the naphthyl-based sensor did not work, the pyrene-based sensor worked and showed a fluorescence change upon addition of a lectin. As opposed to the expectation, the monomer fluorescence increased and the excimer fluorescence decreased as the lectin was added. This finding will be important to develop on-chip lectin sensors. We also succeeded in synthesizing a proton-selective sensor and a tether for a [2+2] photocycloaddition reaction using the pliers-like molecule.

Report

(3 results)
  • 2006 Annual Research Report   Final Research Report Summary
  • 2005 Annual Research Report
  • Research Products

    (23 results)

All 2006 2005

All Journal Article (21 results) Book (2 results)

  • [Journal Article] Synthesis of S-linked thiooligosaccharides analogues of Nod factors : chemoen zymatic synthesis of new thiotrisaccharide intermediates2006

    • Author(s)
      L.L.Morais, H.Yuasa, K.Bennis, I.Ripoche, F.-I.Auzanneau
    • Journal Title

      Can. J. Chem. 84

      Pages: 587-596

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Exploitation of sugar ring flipping for a hinge-type tether assisting a [2+2] cvcloaddition2006

    • Author(s)
      H.Yuasa, M.Nakatani, H.Hashimoto
    • Journal Title

      Org. Biomol. Chem. 4

      Pages: 3694-3702

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Ring flip of carbohydrates : Functions and applications2006

    • Author(s)
      H.Yuasa
    • Journal Title

      Trend. Glycosci. Glycotechnol. 18

      Pages: 353-370

    • NAID

      10018515985

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Journal Article] Synthesis of bisubstrate analogues targeting α-1,3-fucosyltransferase and their activities2006

    • Author(s)
      M.Izumi, S.Kaneko, H.Yuasa, H.Hashimoto
    • Journal Title

      Org. Biomol. Chem. 4

      Pages: 681-690

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of bisubstrate analogues targeting α-1,3-fucosyltransferase and their activities2006

    • Author(s)
      M.Izumi, S.Kaneko, H.Yuasa, H.Hashimoto
    • Journal Title

      Org.Biomol.Chem. 4

      Pages: 681-690

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of S-linked thiooligosaccharides analogues of Nod factors : chemoenzymatic synthesis of new thiotrisaccharide intermediates2006

    • Author(s)
      L.L.Morais, H.Yuasa, K.Bennis, I.Ripoche, F.-I.Auzanneau
    • Journal Title

      Can.J.Chem. 84

      Pages: 587-596

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Exploitation of sugar ring flipping for a hinge-type tether assisting a [2+2] cycloaddition2006

    • Author(s)
      H.Yuasa, M.Nakatani, H.Hashimoto
    • Journal Title

      Org.Biomol.Chem. 4

      Pages: 3694-3702

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Ring flip of carbohydrates : Functions and applications2006

    • Author(s)
      H.Yuasa
    • Journal Title

      Trend.Glycosci.Glycotechnol. 18

      Pages: 353-370

    • NAID

      10018515985

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Top-down and bottom-up nanotechnologies to make carbohydrates more flexible2006

    • Author(s)
      H.Yuasa
    • Journal Title

      Nanotechnology in Carbohydrate Chemistry (Ed. by H.Yuasa)(Transworld Research Network)(India)

      Pages: 127-148

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Tatou no seisei, kouzou, kinou ni manabu2006

    • Author(s)
      H.Yuasa
    • Journal Title

      "fiber" superbiomimetics-kin mirai no shin gijutu sousei(Ed. By T.Motomiya)(NTS)

      Pages: 136-140

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of S-linked thiooligosaccharides analogues of Nod factors : chemoenzymatic synthesis of new thiotrisaccharide intermediates2006

    • Author(s)
      L.L.Morais, H.Yuasa, K.Bennis, I.Ripoche, F.-I.Auzanneau
    • Journal Title

      Can. J. Chem. 84

      Pages: 587-596

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Exploitation of sugar ring flipping for a hinge-type tether assisting a [2+2] cyclozddition2006

    • Author(s)
      H.Yuasa, M.Nakatani, H.Hashimoto
    • Journal Title

      Org. Biomol. Chem. 4

      Pages: 3694-3702

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Synthesis of bisubstrate analogues targeting α-1, 3-fucosyltransferase and their activities2006

    • Author(s)
      M.Izumi, S.Kaneko, H.Yuasa, H.Hashimoto
    • Journal Title

      Org.Biomol.Chem. 4・4

      Pages: 681-690

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of bisubstrate and donor analogues of sialyltransferase and their inhibitory activities2005

    • Author(s)
      M.Izumi, K.Wada, H.Yuasa, H.Hashimoto
    • Journal Title

      J. Org. Chem. 70

      Pages: 8817-8824

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] An improvement in the bending ability of a hinged trisaccharide with the assistanceof a sugar-sugar interaction2005

    • Author(s)
      H.Yuasa, T.Izumi, N.Mitsuhashi, Y.Kajihara, H.Hashimoto
    • Journal Title

      Chem. Eur. J. 11

      Pages: 6478-6490

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and evaluation of 5-thio-L-fucose-containing oligosaccharide2005

    • Author(s)
      M.Izumi, O.Tsuruta, Y.Kajihara, S.Yazawa, H.Yuasa, H.Hashimoto
    • Journal Title

      Chem. Eur. J. 11

      Pages: 3032-30380

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis and evaluation of 5-thio-L-fucose-containing oligosaccharide2005

    • Author(s)
      M.Izumi, O.Tsuruta, Y.Kajihara, S.Yazawa, H.Yuasa, H.Hashimoto
    • Journal Title

      Chem.Eur.J. 11

      Pages: 3032-3038

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary 2005 Annual Research Report
  • [Journal Article] An Improvement in the Bending Ability of a Hinged Trisaccharide with the Assistance of a Sugar-sugar Interaction2005

    • Author(s)
      H.Yuasa, T.Izumi, N.Mitsuhashi, Y.Kajihara, H.Hashimoto
    • Journal Title

      Chem.Eur.J. 11

      Pages: 6478-6490

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Synthesis of Bisubstrate and Donor Analogues of Sialyltransferase and Their Inhibitory Activities2005

    • Author(s)
      M.Izumi, K.Wada, H.Yuasa, H.Hashimoto
    • Journal Title

      J.Org.Chem. 70

      Pages: 8817-8824

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] An improvement in the bending ability of a hinged trisaccharide with the assistance of a sugar-sugar interaction2005

    • Author(s)
      H.Yuasa, T.Izumi, N.Mitsuhashi, Y.Kajihara, H.Hashimoto
    • Journal Title

      Chem.Eur.J. 11

      Pages: 6478-6490

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of bisubstrate and donor analogues of sialyltransferase and their inhibitory activities2005

    • Author(s)
      M.Izumi, K.Wada, H.Yuasa, H.Hashimoto
    • Journal Title

      J.Org.Chem. 70

      Pages: 8817-8824

    • Related Report
      2005 Annual Research Report
  • [Book] Nanotechnology in Carbohydrate Chemistry2006

    • Author(s)
      H.Yuasa
    • Total Pages
      173
    • Publisher
      Transworld Research Network
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Annual Research Report 2006 Final Research Report Summary
  • [Book] "ファイバー"スーパーバイオミメティクス-近未来の新技術創製-2006

    • Author(s)
      湯浅英哉(分担執筆)
    • Total Pages
      1127
    • Publisher
      NTS
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary

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Published: 2005-04-01   Modified: 2016-04-21  

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