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

Development of a novel sugar linkage and its application to the synthesis of bloactive compounds.

Research Project

Project/Area Number 17590013
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionTeikyo University

Principal Investigator

TAKAHASHI Hideyo  Teikyo University, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (10266348)

Co-Investigator(Kenkyū-buntansha) NAMME Rie  Teikyo University, School of Pharmaceutical Sciences, Research assistant, 薬学部, 助手 (70349257)
Project Period (FY) 2005 – 2006
Project Status Completed (Fiscal Year 2006)
Budget Amount *help
¥3,500,000 (Direct Cost: ¥3,500,000)
Fiscal Year 2006: ¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 2005: ¥1,800,000 (Direct Cost: ¥1,800,000)
Keywordscoyolosa / ether-linked sugar / reductive etherification / hypoglycemic activity / oxirane / glycosidation / trehalose / 1C-methyl sugar / Coyolosa / エーテル結合 / アセタール / エーテル
Research Abstract

In 1997, coyolosa was isolated from the Acrocomia mexicana root. It is worth noting that coyolosa, which is a new carbohydrate connected by a ether-linkage, shows a significant effect on the decreasing blood glucose level. So far, no studies on the sugar linkage by ether-bonding have ever been reported. Thus, we examined a novel synthesis of ether-connected pyranoses. We adopted an acetalization-reduction procedure, which is a convenient method for the preparation of ethers under non-basic conditions. Since a two-step procedure is inconvenient, the one-pot reductive etherification was also investigated. Utilizing the method mentioned above, various ether-connected pyranoses were synthesized. Their SAR studies showed that the mannose-connected pyranose has the hypoglycemic activity as potent as coyolosa, suggesting that the correct structure of coyolosa would be the mannose-connected pyranose rather than the proposed allose-connected one. We next examined a new approach utilizing regioselective ring opening of oxirane to give the rare sugars connected by ether linkage.
A novel synthesis of trehalose analogues by the glycosidation of 1C-methyl sugars is also developed.

Report

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

    (22 results)

All 2007 2006 2005 Other

All Journal Article (22 results)

  • [Journal Article] Novel synthesis of carbamate-linked oligosaccharides based on modified Curtius rearrangement.2007

    • Author(s)
      Sawada, Daisuke
    • Journal Title

      European Journal of Organic Chemistry (in press)

    • 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] A facile synthesis of neo-saccharides : 2,6'- and 3,6'-ether-linked sugars.2006

    • Author(s)
      Takahashi, Hideyo
    • Journal Title

      Synthesis

      Pages: 1415-1418

    • 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] Divergent synthesis of L-sugars and L-iminosugars from D-sugars.2006

    • Author(s)
      Takahashi, Hideyo
    • Journal Title

      Chemistry : A European Journal 12

      Pages: 5868-5877

    • 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 1-deoxyhept-2-ulosyl-glycono-1,5-lactone utilizing a-selective O-glycosidation of 2,6-anhydro-1-deoxy-D-hept-1-enitols.2006

    • Author(s)
      Namme, Rie
    • Journal Title

      Tetrahedron 62

      Pages: 9183-9192

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A new and facile synthesis of carbamate- and urea-linked glycoconjugate using modified Curtius rearrangement.2006

    • Author(s)
      Sawada, Daisuke
    • Journal Title

      Tetrahedron Letters 47

      Pages: 7219-7223

    • 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] A facile synthesis of neosaccharides : 2,6'-and 3,6'-ether-linked sugars.2006

    • Author(s)
      Takahashi, Hideyo.
    • Journal Title

      Synthesis

      Pages: 1415-1418

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Divergent synthesis of L-sugars and L-iminosugars from D-sugars.2006

    • Author(s)
      Takahashi, Hideyo.
    • Journal Title

      Chemistry : A European Journal 12

      Pages: 5868-5877

    • 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 1-deoxyhept-2-ulosyl-glycono- 1,5-lactone utilizing α-selective O-glycosidation of 2,6- anhydro-1-deoxy-D-hept-1-enitols.2006

    • Author(s)
      Namme, Rie.
    • Journal Title

      Tetrahedron 62

      Pages: 9183-9192

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] A new and facile synthesis of carbamate-and urea-linked glycoconjugate using modified Curtius rearrangement.2006

    • Author(s)
      Sawada, Daisuke.
    • Journal Title

      Tetrahedron Letters 47

      Pages: 27219-7223

    • 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 1-deoxyhept-2-ulosyl-glycono-1,5-lact utilizing a-selective 0-glycosidation of 2,6-anhydro-1-deoxy-D-hept-1-enitols.2006

    • Author(s)
      Namme, Rie
    • Journal Title

      Tetrahedron 62

      Pages: 9183-9192

    • Related Report
      2006 Annual Research Report
  • [Journal Article] A Facile Synthesis of Neo-saccharides : 2,6'-and 3,6'-Ether-Linked Sugars2006

    • Author(s)
      Takahashi, Hideyo
    • Journal Title

      Synthesis (in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of N-protected azaoligosaccharides and their cyclic derivatives.2005

    • Author(s)
      Sawada, Daisuke
    • Journal Title

      Tetrahedron Letters 46

      Pages: 2399-2403

    • 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 PI-88 analogue using novel O-glycosidation of exo-methylenesugars.2005

    • Author(s)
      Namme, Rie
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3033-3036

    • 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 cyclophellitol utilizing a palladium chloride mediated-Ferrier-II rearrangement.2005

    • Author(s)
      Takahashi, Hideyo
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Short step synthesis of 5-thio-L-hexopyranoses from D-glyconothio-O-lactones.2005

    • Author(s)
      Sawada, Daisuke
    • Journal Title

      Molecules

      Pages: 901-911

    • 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 N-protected azaoligosacchaides and their cyclic derivatives.2005

    • Author(s)
      Sawada, Daisuke.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 2399-3036

    • 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 PI-88 analogue using novel O- glycosidation of exo-methylenesugars.2005

    • Author(s)
      Namme, Rie.
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3033-2403

    • 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 cyclophellitol utilizing a palladium chloride mediated-Ferrier-II rearrangement.2005

    • Author(s)
      Takahashi, Hideyo.
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary
  • [Journal Article] Short-step synthesis of 5-thio-L- hexopyranoses from D-glyconothlo-O-lactones.2005

    • Author(s)
      Sawada, Daisuke.
    • Journal Title

      Heterocycles 66

      Pages: 441-451

    • 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 cyclophellitol utilizing a palladium chloride mediated Ferrier-II rearrangement.2005

    • Author(s)
      Takahashi, Hideyo
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars2005

    • Author(s)
      Namme, Rie
    • Journal Title

      Tetrahedron Letters 46

      Pages: 3033-3036

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Novel synthesis of carbamate-linked ollgosaccharides based on modified Curtius rearrangement.

    • Author(s)
      Sawada, Daisuke.
    • Journal Title

      European Journal of Organic Chemistry (In press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2006 Final Research Report Summary

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi