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Design and Synthesis of Highly Bioactive Sugar-Related Substances

Research Project

Project/Area Number 13470472
Research Category

Grant-in-Aid for Scientific Research (B)

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

Principal Investigator

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

Co-Investigator(Kenkyū-buntansha) HAMAMOTO Hiromi  Teikyo University, School of Pharm. Sci., Res. Associate, 薬学部, 助手 (40365896)
SAWADA Daisuke  Teikyo University, School of Pharm. Sci., Res. Associate, 薬学部, 助手 (00338691)
TAKAHASHI Hideyo  Teikyo University, School of Pharm. Sci., Associate Prof., 薬学部, 助教授 (10266348)
NAMME Rie  Teikyo University, School of Pharm. Sci., Res. Associate, 薬学部, 助手 (70349257)
山田 陽一  帝京大学, 薬学部, 助手 (50317723)
大竹 廣雄  帝京大学, 薬学部, 講師 (50256054)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 2003: ¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 2002: ¥2,800,000 (Direct Cost: ¥2,800,000)
Fiscal Year 2001: ¥8,600,000 (Direct Cost: ¥8,600,000)
KeywordsCoyolosa / Sugar lactone / L-Iduronic acid / 1-Methylglycoside / Selective glycosylation / Cyclitol / Antidiabetic drug / Voglibose / L-ヘキソース / L-リボース / オルトエステル / スピロ糖
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) The conversion of sugar lactones to the hydroxamic acid derivatives by the ring opening operation and the recyclization under Mitsunobu conditions gives the corresponding L-sugar. By applying this conversion technique, L-ribose and L-iduronic acid were also synthesized efficiently
3) Glycosylation using 1-methylenesugar afforded the corresponding α-D-glycoside stereo-selectively. This method could be applied to synthesize the various types of αglycosides such as α-oligosaccharides exhibiting a potent biological activity.

Report

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

    (63 results)

All Other

All Publications (63 results)

  • [Publications] Y.M.A.Yamada: "Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction"Tetrahedron. 60(in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "Oxidation of allylic alcohols, amines, and sulfides mediated by assembled triphase catalyst of phosphotungstate and non-cross-linked amphiphilic copolymer"Tetrahedron. 60(in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Azumaya: "Highly Catalytic Decarboxylative Glycosylation Promoted by Hafnium (IV) Trifluoromethanesulfonate :β-Selective Glycosylacion via a Mixed Carbonate of an Acyl-Protected Donor Sugar"SYNLETT. (in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] R.Iijima: "Novel Biological Function of Sialic Acid (N-Acetylneuraminic Acid) as a Hydrogen Peroxide Scavenger"FEBS Letters. (in press). (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "An Efficient Heterogeneous Heck Reaction Promoted by a New Assembled Catalyst of Palladium and Non-cross-linked amphiphilic Polymer."Tetrahedron Letters. 44. 2379-2382 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] D.Sawada: "Efficient Synthesis of 1-Deoxy-azasugars as Useful Synthetic Tools"Tetrahedron Letters. 44. 3085-3088 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Li, Xiaoliu: "Synthesis of Ketosyl Spiro-Isoxazolidine by 1,3-Dipolar Cycloaddition of 1-Methylene-sugars with Nitrones-a New Access to C-glycosyl Amino Acids"Heterocycles. 59. 547-571 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "Highly Active Catalyst for the Heterogenous Suzuki-Miyaura Reaction : Assembled Complex of Palladium and Non-Crosslinked Amphiphilic Polymer"Journal of Organic Chemistry. 68. 7733-7741 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] R.Namme: "Determining of the Optical Purity of N-nitorosofenfluramine Found in the Chinese Slimming Diet"Yakugakuzasshi. 123. 805-809 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi: "Development of a Novel Sugar Linkage : 6,6'-Ether-connected sugars"Angew.Chem.Int.Ed. 42. 5069-5071 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ohtake: "Synthesis, Structure, and Application of Sugar Orthoesters"J.Synth.Org.Chem.Japan. 66,No.3. 206-217 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "Assembled Catalysts of Titanium and Non-cross-linked Chiral Co-polymer for an Enantioselective Carbonyl-ene Reaction"Tetrahedron Lett.. 43. 3431-3434 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi: "Novel Synthesis of L-Ribose from D-Mannono-1,4-lactone"Org.Lett.. 4(No.14). 2401-2403 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "An Assembled Complex of Palladium and Non-Cross-linked Amphiphilic Polymer : a Highly Active and Recyclable Catalyst for The Suzuki-Miyaura Reaction"Org.Lett.. 4(No.20). 3371-3374 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "Oxidations of Amines and Sulfides Catalyzed by an Assembled Complex of Phosphotungustate and Non-Cross-Linked Amphiphilic Polymer"SYNLETT. 2031-2034 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi: "Novel Synthesis of Enantiomerically Pure Natural Inositols and Their Diastereoisomers"J.Org.Chem. 66(No.8). 2705-2716 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Li, Xiaoliu: "An Efficient Synthesis of New 1'-C-Methyl-α-O-disaccharides Using 1-Methylenesugars as the Glycosyl Donors"Tetrahedron. 57. 4283-4295 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Li, Xiaoliu: "A Facile Synthesis of 1'-C-alkyl-a-disaccharides from 1-C-alkyl-hexopyranoses and Methyl 1-C-methylhexopyranosides."Tetrahedron. 57. 4297-4309 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "Development of a New Triphase Catalyst and Its Application to the epoxidation of Allylic Alcohols"Organic Letters. 3(No.12). 1837-1840 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Li, Xiaoliu: "Stereoselective Synthesis and Structure Elucidation of Spiro-ketodisaccharides"Tetrahedron. 57. 8053-8066 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Li, Xiaoliu: "Direct Methylation of Partially Benzyl-protected Sugar Lactones by Dimethyltitanocene"SYNLETT. No.12. 1885-1888 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Ikegami, H.Takahashi: "創立60周年記念"My Favorite Organic Synthesis""有機合成化学協会. 34-35 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami: "Assembled Catalyst of Palladium and Non-cross-linked Amphiphilic Polymer Ligand for the Efficient Heterogeneous Heck Reaction"Tetrahedron. 60(in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, H.Tabata, M.Ichinohe, H.Takahashi, S.Ikegami: "Oxidation of Allylic Alcohols, Amines, and Sulfides Mediated by Assembled Triphase Catalyst of Phosphotungstate and Non-cross-linked Amphiphilic Copolymer"Tetrahedron. 60(in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] I.Azumaya, M.Kotani, S.Ikegami: "Highly Catalytic Decarboxylative Glycosylation Promoted by Hafnium (IV) Trifluorornethanesulfonate: β-Selective Glycosylation via a Mixed Carbonate of an Acyl-Protected Donor Sugar"SYNLETT. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] R.Iijima, H.Takahashi, S.Ikegami, M.Yaniasaki: "Novel Biological Function of Sialic Acid (N-Acetylneuraminic Acid) as a Hydrogen Peroxide Scavenger"FEBS Letters. (in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] X-L.Li, H.Takahashi, H.Ohtake, S.Ikegami: "1,3-Dipolar Cycloaddition of exo-1-Methylenesugars and Nitrones: Approach to a New Amino-C-Ketosyl Disaccharides"Tetrahedron Lett.. 45(in press). (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] X-L.Li, H.Takahashi, H.Ohtake, S.Ikegami: "Synthesis of Ketosyl Spiro-Isoxazolidine by 1,3-Dipolar Cycloaddition of 1-Methylenesugars and Nitrones -A New Access to C-Glycosyl Amino Acids"Heterocycles. 59(No.2). 547-571 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami: "An Efficient Heterogeneous Heck Reaction Promoted a New Assembled Catalyst of Palladium and Non-cross-linked Amphiphilic Polymer Tetrahedron"Tetrahedron Lett.. 44(No.11). 2379-2382 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] D.Sawada, H.Takahashi, S.Ikegami: "Efficient Synthesis of 1-Deoxy-Azasugars as Useful Synthetic Tools"Tetrahedron Lett.. 44(No.15). 3085-3088 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami: "Highly Active Catalyst for the Heterogeneous Suzuki-Miyaura Reaction: Assembled Complex of Palladium and Non-Cross-Linked Amphiphilic Polymer"J. Org. Chem.. 68(No.20). 7733-7741 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Nakadai, H.Inagaki, M.Minami, H.Takahashi, R.Namme, M.Ohsawa, S.Ikegami: "Determination of the Optical Purity of N-Nitrosofenfluramine found in the Chinese Slimming Diet"Yakugaku Zasshi (Japanese). 123(9). 805-809 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi, T.Fukuda, H.Mitsuzuka, R.Namme, H.Miyamoto, Y.Ohkura, S.Ikegami: "Development of a Novel Sugar Linkage"Angew. Chem., mt. Ed.. 42(No.41). 5069-5071 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Ohtake, X.Li, H.Takahashi, S.Ikegami: "Synthesis, Structure, and Application of Sugar Orthoesters"J. Synth. Org. Chem. Japan(Japanese). 60, No.3. 206-127 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, M.Ichinohe, H.Takahashi, S.Ikegami: "Assembled Catalysts of Titanium and Non-cross-linked Chiral Copolymer for an Enantioselective Carbonyl-ene Reaction"Tetrahedron Lett.. 43. 3431-3434 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi, Y.Iwai, Y.Hitomi, S.Ikegami: "Novel Synthesis of L-Ribose from D-Mannono-1,4-lactone"Org. Lett.. 4(No.14). 2401-2403 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami: "An Assembled Complex of Palladium and Non-Cross-linked Amphiphilic Polymer: a Highly Active and Recyclable Catalyst for the Suzuki-Miyaura Reaction"Org. Lett.. 4(No.20). 3371-3374 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, K.Takeda, H.Takahashi, S.Ikegami: "Oxidations of Amines and Sulfides Catalyzed by an Assembled Complex of Phosphotungustate and Non-Cross-Linked Amphiphilic Polymer"SYNLETT. 2031-2034 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Takahashi, H.Kittaka, S.Ikegami: "Novel Synthesis of Enantiomerically Pure Inositols and Their Diastereoisomers"J. Org. Chem.. 66, No.8. 2705-2716 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] X-L.Li, H.Ohtake, H.Takahashi, S.Ikegami: "An Efficient Synthesis of New 1-C-Methyl-c-O-disaccharides using 1-Methylenesugars as the Glycosyl Donors"Tetrahedron. 57. 4283-4295 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] X-L.Li, H.Ohtake, H.Takahashi, S.Ikegami: "An Efficient Synthesis of New 1-C-Methyl-c-O-disaccharides using 1-Methylenesugars as the Glycosyl Donors"Tetrahedron. 57. 4297-4309 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada, M.Ichinohe, H.Takahashi, S.Ikegami: "Development of a New Triphase Catalyst and Its Application to Epoxidation of Allylic Alcohols"Org. Lett.. 3, No.12. 1837-1840 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] SYNLETT: "Stereoselective Synthesis and Structure Elucidation of Spiro-ketodisaccharides"Tetrahedron. 57. 8053-8066 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] X-L.Li, H.Ohtake, H.Takahashi, S.Ikegami: "Direct Methylenation of Partially Benzyl-protected Sugar Lactones by Dimethylt.itinocene"SYNLETT. No.12. 1885-1888 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Ikegami, H.Takahashi: "Synthetic Studies of Biologically Valuable Substances"My Favorite Organic Synthesis, The 60^<th> Anniversary of the Soc. Synth. Org. Chem., Japan. 34-35 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.M.A.Yamada: "An Efficient Heterogeneous Heck Reaction Promoted by a New Assembled Catalyst of Palladium and Non-cross-linked amphiphilic Polymer."Tetrahedron Letters. 44. 2379-2382 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] D.Sawada: "Efficient Synthesis of 1-Deoxy-azasugars as Useful Synthetic Tools"Tetrahedron Letters. 44. 3085-3088 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Li, Xiaoliu: "Synthesis of Ketosyl Spiro-Isoxazolidine by 1,3-Dipolar Cycloaddition of 1-Methylene-sugars with Nitrones-a New Access to C-glycosyl Amino Acids"Heterocycles. 59. 547-571 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.M.A.Yamada: "Highly Active Catalyst for the Heterogenous Suzuki-Miyaura Reaction : Assembled Complex of Palladium and Non-Crosslinked Amphiphilic Polymer"Journal of Organic Chemistry. 68. 7733-7741 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] R.Namme: "Determining of the Optical Purity of N-nitorosofenfluramine Found in the Chinese Slimming Diet"Yakugaku Zasshi. 123. 805-809 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Takahashi: "Development of a Novel Sugar Linkage : 6,6'-Ether-connected sugars"Angew.Chem., Int.Ed. 42. 5069-5071 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] S.Ikegami, H.Takahashi: "創立60周年記念"My Favorite Organic Synthesis""有機合成化学協会. 34-35 (2002)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Ohtake: "Synthesis, Structures and Application of Sugar Orthoesters"J.Synth.Org.Chem.Japan. 60, No.3. 206-217 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.M.A.Yamada: "Assembled Catalysts of Titanium and Non-cross-linked Chiral Copolymer for an Enantioselective Carbonyl-ene Reaction"Tetrahedron Lett.. 43. 3431-3434 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Takahashi: "Novel Synthesis of L-Ribose from D-Mannono-1,4-lactone"Org.Lett.. 4(No.14). 2401-2403 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.M.A.Yamada: "An Assembled Complex of Palladium and Non-Cross-linked Amphiphilic Polymer : a Highly Active and Recyclable Catalyst for the Suzuki-Miyaura Reaction"Org.Lett.. 4(No.20). 3371-3374 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Y.M.A.Yamada: "Oxidations of Amines and Sulfides Catalyzed by an Assembled Complex of Phosphotungustate and Non-Cross-Linked Amphiphilic Polymer"SYNLETT. 2031-2034 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] Xiaoliu Li: "Direct Methylenation of Partially Benzyl-protected Sugar Lactones by Dimethyltitinocene"Synlett. 1885-1888 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Xiaoliu Li: "Stereoselective Synthesis and Structure Elucidation of Spiro-ketodisaccharides"Tetrahedron. 57. 8053-8066 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.M.A. Yamada: "Development of a New Triphase Catalyst and Its Application to Epoxidation of Allylic Alcohols"Organic Letters. 3. 1837-1840 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Xiaoliu Li: "A Facile Synthesis of 1Af-C-Alkyl-a-disaccharides from 1-C-Alkylhexopyranoses and Methyl 1-C-Alkyl-hexopyranosides"Tetrahedron. 57. 4297-4309 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Xiaoliu Li: "An Efficient Synthesis of New 1-C-Methyl-a-O-disaccharides using 1-Methylenesugars as the Glycosyl Donors"Tetrahedron. 57. 4283-4295 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hideyo Takahashi: "Novel Synthesis of Enantiomerically Pure Inositols and Their Diastereoisomers"The Journal of Organic Chemistry. 66. 2705-2716 (2001)

    • Related Report
      2001 Annual Research Report

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

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