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2001 Fiscal Year Final Research Report Summary

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)
Project Period (FY) 2000 – 2001
KeywordsGlycosides / Fullerene / Glycoconjugate / Glycosylation / Glycosyltromsferase / Shiga toxins / Active Oxygen / Fullerenal
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.

  • Research Products

    (15 results)

All Other

All Publications (15 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 2003-09-17  

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