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CONSTRUCTION OF FUNCTIONAL MOLECULES USING FLEXIBILITY AND ALLOSTERY OF HINGE SUGAR

Research Project

Project/Area Number 13680668
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioorganic chemistry
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) 2001 – 2004
Project Status Completed (Fiscal Year 2004)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2004: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 2003: ¥600,000 (Direct Cost: ¥600,000)
Fiscal Year 2002: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2001: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsMolecular Devices / Molecular Machines / Hinge Sugar / Functional Oligosaccharides / Biosensors / Fluorescent Sensors / Excimer Complex / Molecular Pliers / オリゴマンノシド / コンカナバリンA / 金属錯体 / リングフリップ
Research Abstract

Hinge motions play crucial roles in the functions of motor proteins, signal transducers, and allosteric enzymes. Thus, mimicking the hinge regions of these natural molecular machines with small molecules is the basis for the construction of smaller molecular machines and devices. We brought β-xylopyranosides into focus as potential hinge molecules, because these molecules are prone to undergo a ring-flip, which accompanies the conversion of the all equatorial substituents into axial orientations in a pliers-like manner. The same ring-flip is more difficult with the corresponding substituted-cyclohexanes because of the lack of anomeric effect and the existence of an additional axial hydrogen atom. In our continuing efforts to create molecular devices from xylopyranosides, we invented "hinge sugars," 2,4-diamino-2,4-dideoxy-β-xylopyranosides, which shifts the conformation from C1 to 1C in response to a metal ion. In this stucy, we were able to fix this hinge sugar in 1C conformation by forming a Pt^<2+> complex or by N,N'-carbonylation. With this hinge sugar in hand, we were also able to build a metal ion sensor, 1,3-dipyrenylmethyl-hmge sugar. Chelation of the diamino group to the metal ion causes the ring flip of hinge sugar, leading the diequatorial pyrenyl groups into the diaxial orientations. The parallel pyrene groups afford an excimer fluorescence. These findings are important for the construction of molecular machines and molecular devices in the future.

Report

(5 results)
  • 2004 Annual Research Report   Final Research Report Summary
  • 2003 Annual Research Report
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (15 results)

All 2004 2003 Other

All Journal Article (6 results) Patent(Industrial Property Rights) (1 results) Publications (8 results)

  • [Journal Article] Switching extended 1,3-diequatorial and bent 1,3-diaxial satates of a disubstituted hinge sugar by ligand exchange reactions on Pt(II)2004

    • Author(s)
      T.Izumi, H.Hashimoto, H.Yuasa
    • Journal Title

      Chem.Commun. 1

      Pages: 94-95

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Hinge Sugar as a Movable Component of an Ecimer Fluorescence Sensor2004

    • Author(s)
      H.Yuasa, N.Miyagawa, T.Izumi, M.Nakatani, M.Izumi, H.Hashimoto
    • Journal Title

      Org.Lett. 6・9

      Pages: 1489-1492

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] A tongs-like fluorescence sensor for metal ions : perfect conformational switch of hinge sugar by a pyrene stacking2004

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

      Org.Biomol.Chem. 2・24

      Pages: 3548-3556

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Annual Research Report 2004 Final Research Report Summary
  • [Journal Article] Switching extended 1,3-diequatorial and bent 1,3-diaxial satates of a disubstituted hinge sugar by ligand exchange reactions on Pt(II)2004

    • Author(s)
      T.Izumi, H.Hashimoto, H.Yuasa
    • Journal Title

      Chem.Commun.

      Pages: 94-95

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] Hinge Sugar as a Movable Component of an Ecimer Fluorescence Sensor2004

    • Author(s)
      H.Yuasa, N.Miyagawa, T.Izumi, M.Nakatani, M.Izumi, H.Hashimoto
    • Journal Title

      Org.Lett. 6

      Pages: 1489-1492

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Journal Article] A tongs-like fluorescence sensor for metal ions : perfect conformational switch of hinge sugar by a pyrene stacking2004

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

      Org.Biomol.Chem. 2

      Pages: 3548-3556

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Patent(Industrial Property Rights)] いす形6員環単糖化合物2003

    • Inventor(s)
      湯浅 英哉, 深江 一博
    • Industrial Property Rights Holder
      大塚化学株式会社
    • Industrial Property Number
      2003-186712
    • Filing Date
      2003-06-30
    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2004 Final Research Report Summary
  • [Publications] M.Izumi, S.Okumura, H.Yuasa, H.Hashimoto: "Mannose-BSA conjugates : comparison between commercially available linkers in reactivity and bioactivity"J.Carbohydr.Chem.. 22・5. 317-329 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] O.Tsuruta, H.Yuasa, H.Hashimoto, K.Sujino, A.Otter, H.Li, M.M.Palcic: "Synthesis of GDP-5-thiosugars and their use as glycosyl donor substrates for glycosyltransferases"J.Org.Chem.. 68・16. 6400-6406 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] T.Izumi, H.Hashimoto, H.Yuasa: "Switching extended 1,3-diequatorial and bent 1,3-diaxial states of a disubstituted hinge sugar by ligand exchange reactions on Pt(II)"Chem.Commun.. 1. 94-95 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Yuasa, M.Izumi, H.Hashimoto: "Thiasugars as potential glycosidase inhibitor"J.Synthetic Org.Chem.. 60・8. 774-782 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Yuasa, C.Saotome, O.Kanie: "Design sythese of inhibitors of glycoenzymes"Trend.Glycosci.Glycotechnol.. 14. 231-251 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Izumi, S.Okumura, H.Yuasa, H.Hashimoto: "Mannose-BSA conjugates : comparison between commercially available linkers in reactivity and bioactivity"J.Carbohydr.Chem.. (発表予定).

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Yuasa, J.Takada, H.Hashimoto: "Glycosidase inhibition by cyclic salfonium compounds"Bioorg. Med. Chem. Lett.. 11・9. 1137-1139 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Agawa, A.Maruyama, T.Odagiri, H.Yuasa, H.Hashimoto: "Pseudosagars, 42, Synthesis and biological evaluation of α-L-fucosidase inhibitors :5a-carba-α-L-fucopyranosylamine and related compounds"Eur. J. Org. Chem.. 5. 967-974 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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