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Design and Synthesis of Highly Bioactive Sugar-Related Substances

Research Project

Project/Area Number 16590013
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

IKEGAMI Shiro  Teikyo University, School of Pharmaceutical Sciences, Professor, 薬学部, 教授 (10119555)

Co-Investigator(Kenkyū-buntansha) TAKAHASHI Hideyo  Teikyo University, School of Pharm.Sci., Associate Prof., 薬学部, 助教授 (10266348)
SAWADA Daisuke  Teikyo University, School of Pharm.Sci., Res.Associate, 薬学部, 助手 (00338691)
HAMAMOTO Hiromi  Teikyo University, School of Pharm.Sci., Res.Associate, 薬学部, 助手 (40365896)
NAMME Rie  Teikyo University, School of Pharm.Sci., Res.Associate, 薬学部, 助手 (70349257)
Project Period (FY) 2004 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2005: ¥1,400,000 (Direct Cost: ¥1,400,000)
Fiscal Year 2004: ¥2,200,000 (Direct Cost: ¥2,200,000)
KeywordsCoyolosa / Sugar lactone / L-Iduronic acid / 1-Methylglycoside / Selective glycosylation / Cyclitol / Antidiabetic drug / Voglibose / 新規エーテル糖構築法 / ボグリボース
Research Abstract

The following research results have been obtained in this research project.
1) Coyolosa which is a natural disaccharide having an unusual structure with a 6,6'-ether- linkage was successfully synthesized. In connection with its anti-diabetic activity, 10 kinds of analogs have been synthesized and it was concluded that the reported structure should be revised. A 6,6'-disaccharide formed from two molecules of mannose might be proposed.
2) In the connection of the conversion technique for D-sugar to the corresponding L-sugar with the ring opening and the recyclization, this methodology could be applied to the effective formation of L-aza-sugars and L-thia-sugars.
3) Glycosylation using 1-methylenesugar afforded the corresponding α-D-glycoside stereo-selectively. This method could be also applied to synthesize the various types of α-glycosides such as α-oligosaccharides exhibiting a potent biological activity. The penta-saccharide analogue for PI-88 that will be expected as a heparanase inhibitor could be synthesized in a fully protected form.

Report

(3 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • Research Products

    (34 results)

All 2006 2005 2004 2003

All Journal Article (34 results)

  • [Journal Article] A Facile Synthesis of Neo-saccharides : 2,6'- and 3,6'-Ether-Linked Sugars, Synthesis2006

    • Author(s)
      Hideyo Takahashi
    • Journal Title

      Synthesis (in press)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Facile Synthesis of Neo-saccharides : 2,6'- and 3,6'-Ether-Linked Sugars2006

    • Author(s)
      H.Takahashi, H.Mitsuzuka, K.Nishiyama, S.Ikegami
    • Journal Title

      Synthesis (in press)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Facile Synthesis of Neo-saccharides : 2,6' and 3,6'-Ether-Linked Sugars, Synthesis2006

    • Author(s)
      Hideyo Takahashi
    • Journal Title

      Synthesis (in press)

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of Cyclophellitol utilizing Palladium Chloride Meddiated-Ferrier-II Rearrange- ment2005

    • Author(s)
      Hideyo Takahashi
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of N-Protected Azaoligosaccharides and Their Cyclic Derivatives2005

    • Author(s)
      Daisuke Sawada
    • Journal Title

      Tetrahedron Letters 46 (No.14)

      Pages: 2399-2403

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of PI-88 Analogue Using Novel O-Glycosidation of exo-Methylenesugars2005

    • Author(s)
      Rie Narume
    • Journal Title

      Tetrahedron Letters 46 (No. 17)

      Pages: 3033-3036

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Novel Recyclable Catalytic System Utilizing Temperature-Responsive Catalyst2005

    • Author(s)
      Hiromi Hamamoto
    • Journal Title

      Angew. Chem., Int. Ed. 44

      Pages: 4536-4538

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Short-Step Synthesis of 5-Thio-L-hexopyranoses from D-Gluconothio-O-lactone2005

    • Author(s)
      Daisuke Sawada
    • Journal Title

      Heterocycles 66

      Pages: 441-451

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Annual Research Report 2005 Final Research Report Summary
  • [Journal Article] Synthesis of Cyclophellitol utilizing Palladium Chloride Mediated-Ferrier-II Rearrangement2005

    • Author(s)
      H.Takahashi, S.Ikegami
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of N-Protected Azaoligosaccharides and Their Cyclic Derivatives2005

    • Author(s)
      D.Sawada, H.Takahashi, M.Shiro, S.Ikegami
    • Journal Title

      Tetrahedron Lett. 46(No.14)

      Pages: 2399-2403

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of PI-88 Analogue Using Novel O-Glycosidation of exo-Methylenesugars2005

    • Author(s)
      R.Namme, T.Mitsugi, H.Takahashi, S.Ikegami
    • Journal Title

      Tetrahedron Lett. 46(No.17)

      Pages: 3033-3036

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Novel Recyclable Catalytic System Utilizing Temperature-Responsive Catalyst2005

    • Author(s)
      H.Hamamoto, Y.Suzuki, H.Takahashi, S.Ikegami
    • Journal Title

      Angew.Chem.Int.Ed. 44

      Pages: 4536-4538

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Short-Step Synthesis of 5-Thio-L-hexopyranoses from D-Gluconothio-O-lactone2005

    • Author(s)
      D.Sawada, S.Sasayama, H.Takahashi, S.Ikegami
    • Journal Title

      Heterocycles 66

      Pages: 441-451

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Synthesis of Cyclophellitol utilizing Palladium Chloride Meddiated-Ferrier-II Rearrangement2005

    • Author(s)
      Hideyo Takahashi
    • Journal Title

      Molecules 10

      Pages: 901-911

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of N-Protected Azaoligosaccharides and Their Cyclic Derivatives2005

    • Author(s)
      Daisuke Sawada
    • Journal Title

      Tetrahedron Letters 46(No.14)

      Pages: 2399-2403

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthesis of PI-88 Analogue Using Novel O-Glycosidation of exo-Methylenesugars2005

    • Author(s)
      Rie Namme
    • Journal Title

      Tetrahedron Letters 46(No.17)

      Pages: 3033-3036

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A Novel Recyclable Catalytic System Utilizing Temperature-Responsive Catalyst2005

    • Author(s)
      Hiromi Hamamoto
    • Journal Title

      Angew.Chem., Int.Ed. 44

      Pages: 4536-4538

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Assembled Gatalyst of Palladium and Non-cross-linked Amphiphilic Polymer Ligand for the Efficient Heterogeneous Heck Reaction2004

    • Author(s)
      Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami^*
    • Journal Title

      Tetrahedron 60(No.18)

      Pages: 4097-4105

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Oxidation of Allylic Alcohols, Amines, and Sulfides Mediated by Assembled Triphase Catalyst of Phosphotungstate and Non-cross-linked Amphiphilic Copolymer2004

    • Author(s)
      Y.M.A.Yamada, H.Tabata, M.Ichinohe, H.Takahashi, S.Ikegami^*
    • Journal Title

      Tetrahedron 60(No.18)

      Pages: 4087-4096

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Highly Catalytic Decarboxylative Glycosylation Promoted by Hafnium (IV) Trifluoromethanesulfonate : β-Selective Glycosylation via a Mixed Carbonate of an Acyl-Protected Donor Sugar2004

    • Author(s)
      I.Azumaya, M.Kotani, S.Ikegami^*
    • Journal Title

      SYNLETT

      Pages: 959-962

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Novel Biological Function of Sialic Acid (N-Acetylneuraminic Acid) as a Hydrogen Peroxide Scavenger2004

    • Author(s)
      R.Iijima, H.Takahashi, S.Ikegami, M.Yamasaki
    • Journal Title

      FEBS Letters 561

      Pages: 163-166

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] 1,3-Dipolar Cycloaddition of exo-1-Methylenesugars and Nitrones : Approach to a New Amino-C-Ketosyl Disaccharides2004

    • Author(s)
      X-L.Li, H.Takahashi, H.Ohtaka, S.Ikegami
    • Journal Title

      Tetrahedron Lett. 45(No.21)

      Pages: 4123-4126

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Oxidation of allylic alcohols, amines, and sulfides mediated by assembled triphase catalyst of phosphotungstate and non-cross-linked amphiphilic copolymer2004

    • Author(s)
      Y.M.A.Yamada
    • Journal Title

      Tetrahedron 60(No.18)

      Pages: 4087-4096

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction2004

    • Author(s)
      Y.M.A.Yamada
    • Journal Title

      Tetrahedron 60(No.18)

      Pages: 4097-4105

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Highly Catalytic Decarboxylative Glycosylation Promoted by Hafnium (IV) Trifluoromenthanesulfonate : β-Selective Glycosylation via a Mixed Carbonate of an Acyl-Protected Donor Sugar2004

    • Author(s)
      I.Azumaya
    • Journal Title

      SYNLETT

      Pages: 959-962

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Novel Biological Function of Sialic Acid (N-Acetylneuraminic Acid) as a Hydrogen Peroxide Scavenger2004

    • Author(s)
      R.Iijima
    • Journal Title

      FEBS Letters 561

      Pages: 163-166

    • Related Report
      2004 Annual Research Report
  • [Journal Article] 1,3-Dipolar Cycloaddition of exo-l-Methylenesugars and Nitrones : Approach to New Amino-C-Ketosyl Disaccharides2004

    • Author(s)
      X-L.Li
    • Journal Title

      Tetrahedron Lett. 45(No.21)

      Pages: 4123-4126

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of L-Iduronic Acid from 5-Enopyranoside by Diastereoselective Hydroboration/Oxdation2004

    • Author(s)
      H.Takahashi
    • Journal Title

      Synthesis No.18

      Pages: 2991-2994

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Synthesis of Ketosyl Spiro-Isoxazolidine by 1,3-Dipolar Cycloaddition of 1-Methylenesugars and Nitrones - A New Access to C-Glycosyl Amino Acids2003

    • Author(s)
      X-L.Li, H.Takahashi, H.Ohtaka, S.Ikegami^*
    • Journal Title

      Heterocycles 59(No.2)

      Pages: 547-571

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] An Efficient Heterogeneous Heck Reaction Promoted a New Assembled Catalyst of Palladium and Non-cross-linked Amphiphilic Polymer2003

    • Author(s)
      Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami^*
    • Journal Title

      Tetrahedron Lett. 44(No.11)

      Pages: 2379-2382

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Efficient Synthesis of 1-Deoxy-Azasugars as Useful Synthetic Tools2003

    • Author(s)
      D.Sawada, H.Takahashi, S.Ikegami^*
    • Journal Title

      Tetrahedron Lett 44(No.15)

      Pages: 3085-3088

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Highly Active Catalyst for the Heterogeneous Suzuki-Miyaura Reaction : Assembled Complex of Palladium and Non-Cross-Linked Amphiphilic Polymer2003

    • Author(s)
      Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami^*
    • Journal Title

      J.Org.Chem. 68(No.20)

      Pages: 7733-7741

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Determination of the Optical Purity of N-Nitrosofenfluramine found in the Chinese Slimming Diet2003

    • Author(s)
      A.Nakadai, H.Inagaki, M.Minami, H.Takahashi, R.Namme, M.Ohsawa, S.Ikegami^*
    • Journal Title

      Yakugaku Zasshi (Japanese) 123(9)

      Pages: 805-809

    • NAID

      110003614927

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Development of a Novel Sugar Linkage : 6,6'-Ether-Connected-Sugars2003

    • Author(s)
      H.Takahashi, T.Fukuda, H.Mitsuzuka, R.Namme, H.Miyamoto, Y.Ohkura, S.Ikegami^*
    • Journal Title

      Angew.Chem., Int.Ed. 42(No.41)

      Pages: 5069-5071

    • NAID

      130006997354

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary

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Published: 2004-04-01   Modified: 2016-04-21  

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