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Syriltes and Biologlacal Enaluativns of Fulkren-Glycosidet.

Research Project

Project/Area Number 12660096
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Bioproduction chemistry/Bioorganic chemistry
Research InstitutionNagoya University

Principal Investigator

NISHIDA Yoshihiro  Nagoya University Engineering, Ass. Prof., 工学研究科, 助教授 (80183896)

Co-Investigator(Kenkyū-buntansha) MATSUDA Kazuhiro  Nagoya University National Cancer Inst. Chief, ウイルス部, 主任研究官 (80251502)
KOBAYASHI Kazukiyo  Nagoya University Engineering, Ass. Prof., 工学研究科, 教授 (10023483)
松浦 和則  名古屋大学, 工学研究科, 助手 (60283389)
Project Period (FY) 2000 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 2001: ¥1,100,000 (Direct Cost: ¥1,100,000)
Fiscal Year 2000: ¥1,400,000 (Direct Cost: ¥1,400,000)
KeywordsGlycosides / Fullerene / Glycoconjugate / Glycosylation / Glycosyltromsferase / Shiga toxins / Active Oxygen / Fullerenal / フレノール / 生理活性 / 糖鎖結合フラーレン / 糖転移酵素 / セレクチン / L-糖
Research Abstract

In this research project, a new type of glycoconjugates, namely, "fullerene g ycoconjugates ' was designed and developed. The C60 conjugates are composed of biologically active active giycosides introduced onto the surface via an N-glycoside linkage. The different property of the two molecules regarding from both physicchemical and biological aspects is expected to induce a novel class of biologically active compounds.
Prior to the synthesis of the'Tullerene glycoconjugates", an efficient glycosylation method was deveioped, which involved the use of new thio-glycosyl donors and galactosyltransferase. The new thio-glycosyl donor was applied conveniently to the formation of globotn- and biosides possessing high biological potential to trap Shiga toxins and deactivate the toxins. A bovine galactosyltransferase was found to catalyse a novel class of enzymic reactions applicable to non-natural L-sugars and acyclic substrates.
Several types of biologiclaly active saccharides were coupled with C60 fullerene via thermal couplmg between a glycoylazide and C60. The derived fullerene glycococonjugates as well as fullerenol conjugates were water-miscible and proved to show high biological potential to block carbohydrate-protein binding involved in many biological phenomena.

Report

(3 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • Research Products

    (25 results)

All Other

All Publications (25 results)

  • [Publications] H Kato (他 10名): "Syntheses and EELS characterization of Water-Soluble Multi-Hydroxyl GdaC82 Fullerenols"Chem. Phys. Lett.. 324. 255-259 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Nishida (他 3名): "The First Bovine β1,4-Galactosyltransferase Reaction with an Acyclic Accepter Substrate"Org. Lett.. 3. 1-3 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Nishida (他 3名): "Crystal Structure of Methyl 5-Acetamido-2-t-butyl-2-methyl-1,3-benzodioxde-4-carboxylate"Anal. Sci.. 17. 685-686 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H Kato (他 5名): "Syntheses and Biological Evaluations of α-D-Mannosyl [60]Fullerenols"Bioorg. Med. Chem. Lett.. 11. 2935-2937 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H.Dohi (他 7名): "Molecular Design and Biological Potential of Galactotype Trehalose as a Non-natural Ligand of Shiga Toxins"Org. Lett.. 4. 355-357 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H.Dohi (他 3名): "O-Methorycarbonylphenyl-1-thio-β-D-galactopyranoside, a non-malodorous Thio Glycosylaition Donor"SynLett.. (NO9). 1446-1448 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Tanaka, Y. Nishida, K. Kobayashi: "A Facile Synthesis of a Cationic Neoglycoconjugate Polymer Carrying 3,6-Branched a-D-Mannosyl Trisaccahride Cluster,"J. Carbohydr. Chem.. 19. 413-418 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Nishida, H. Tamakoshi, Y. Kitagawa, K. Kobayashi, J. Thiem: "A Novel Bovine (31,4-Galactosyltransferase Reactions to Yield p-D-Galactosyl(l-3)-linkage with L-Series Sugars Substrates"Angew.Chem.. 112. 2074-2077 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Nishida, H. Uzawa, T. Toba, K. Sasaki, H.: "A Facile Synthesis ofL- and P-Selectin Blockers via Copolymerization of Vinyl Monomers Constructing the Key Carbohydrate Modules of Sulfated LewisX Mimics"Biomacromolecules.. 1. 68-78 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] A. Yashiro, Y. Nishida, K. Kobayashi, M. Ohno: "Beta-Hydroxy Nitrite and beta-Hydroxy Qxime Derivatives of [60]fullerene by Nucleophilic Ring Cleavage of Fulleroisoxazoline and Isoxazolidine in the Presence of Methanol"Synlett. 361-362 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] H. Kato, K. Suenaga, M Mikawa, M. Okumura, N. Miwa, A. Yashiro, H. Fujimura, A. Mizuno, Y.Nishida, K. Kobayashi, H. Shinohara: "Syntheses and EELS Characterization of Water-Soluble Multi-Hydroxyl Gd@C82 Fullerenols"Chem. Phys. Lett.. 324. 255-259 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y. Nishida, H. Tamakoshi, K. Kobayashi, J. Thienm: "8The First Bovine beta-1,4-Galactosyltransferase Reaction with an Acyclic Acceptor Substrate, 3 -Acetamido- l , 2-propanediol to Yield 3 - Q-beta-D-Galactopyranosyl-sn-glyceroI Skeleton"Org Lett.. 3. 1-3 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Yoshihiro Nishida, Masaya Suzuki and Kazukiyo Kobayashi, Yoshiharu Toriumi and Hideki Hashimoto: "Crystal Structure of Methyl 5-Acetamido-2-t-butyl-2-methyl-1,3 - enzodioxole-4-car boxylate"Anal. Sci.. 17. 685-686 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Haruhito Kato, Arihiro Yashiro, Akiko Mizuno, Yoshihiro Nishida, Kazukiyo Kabayashi, and Hisanori Shinohara: "Syntheses and Biological Evaluations of a-D-Mannosyl [60]Fullerenols"Biorog. Med. Chem. Lett. 11. 2935-2937 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Hirofumi Dohi, Yoshihiro Nishida, Yuki Furuta, Hirotaka Uzawa, Shin-ichiro Yokoyama, Saori Ito, Hiroshi Mori, Kazukiyo Kobayashi: "Molecular Design and Biological Potential of Galacto-type Trehalose as a Non-natural Ligand of Shiga Toxins"Org. Lett.. 4. 355-357 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Y.Nishida(他3名): "The First Bovine beta-1,4-Galactosyltransferase Reaction with an Acyclic Acceptor Substrate, 3-Acetamido-1,2-propanediol"Org. Lett. 3. 1-3 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.Nishida(他3名): "Crystal Structure of Methyl 5-Acetamido-2-t-butyl-2-methyl-1,3-benzodioxole-4-carboxylate"Anal Sci. 17. 685-686 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Kato(他5名): "Syntheses and Biological Evaluations of a-D-Mannosyl [60] Fullerenols"Bioorg.Med.Chem.Lett.,. 11. 2935-2937 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Dohi(他7名): "Molecular Design and Biological Potential of Galacto-type Trehalose as a Non-natural Ligand of Shiga Toxins"Org. Lett.,. 4. 355-357 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Dohi(他3名): "Methylsalicyl β-D-Galactopyranoside, A Non-Maloderous Thio Glycosylation Donor For the Synthesis of Globosyl α(1-4)-Linkages"Synlett.,. NO9. 1446-1448 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Y.NISHIDA (他4名): "A Novel Bovine β1, 4-Galactosyltransferase Reactions to Yield β-D-Galactosyl (1-3)-linkage with L-Series Sugars Substrates"Angew.Chem.Int.Ed.,. 39. 2000-2003 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.NISHIDA(他4名): "A Facile Synthesis of L- and P-Selectin Blockers via Copolymerization of Vinyl Monomers Constructing the Key Carbohydrate Modules of Sulfated LewisMimics"Biomacromolecules. 1. 68-74 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] A.YASHIRO(他4名): "Beta-Hydroxy Nitrile and beta-Hydroxy Oxime Derivatives of [60]fullerene by Nucleophilic Ring Cleavage of Fulleroisoxazoline and Isoxazolidine in the Presence of Methanol"Synlett. 361-362 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] H.KATO(他10名): "Syntheses and EELS Characterization of Water-Soluble Multi-Hydroxyl Gd@C82 Fullerenols"Chem.Phys.Lett.,. 324. 255-259 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Y.NISHIDA(他3名): "The First Bovine beta-1, 4-Galactosyltransferase Reaction With an Acyclic Acceptor Substrate, 3-Acetamido-1, 2-propanediol to Yield 3-O-beta-D-Galactopyranosyl-sn-glycerol Skeleton"Org.Lett.. 3. 1-3 (2001)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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