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2003 Fiscal Year Final Research Report Summary

Basic Research on Discovery and Functions of Novel Physiologically Active Complex Carbohydrates

Research Project

Project/Area Number 12306007
Research Category

Grant-in-Aid for Scientific Research (A)

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

Principal Investigator

KISO Makoto  Gifu University, Agriculture, Professor, 農学部, 教授 (90092931)

Co-Investigator(Kenkyū-buntansha) ANDO Susumu  Tokyo Metropolitan Institute of Gerontology, Biomembrane, Vice-president, 生体膜部門, 副所長(研究職) (30073000)
KANNNAGI Reiji  Aichi Cancer Center, Pathology, Director, 病理学第二部, 部長(研究職) (80161389)
ISHIDA Hideharu  Gifu University, Agriculture, Associate Professor, 農学部, 助教授 (20203002)
Project Period (FY) 2000 – 2003
Keywordsselectin / ganglioside / sialic acid / sialyl Lewis X / sialyl Lewis A / siglec / CD38 / glycolipids
Research Abstract

[1]Systematic synthesis of newly discovered sulfated sialyl Lewis X variants and elucidation of a novel immunity regulation system : It has been demonstrated at the molecular level, for the first time, that the de-N-acetylation of sialic acid (activation) and lactamization (inactivation) are the key reactions in the L-selectin ligand processing by the systematic precise synthesis (Carbohydr.Res.,338,2793-2812,2003). Thus, the highly efficient total synthesis of sialyl 6-O-sulfo Lewis X hexasaccharide gangliosides and sialyl 6-O-sulfo paraglobosides containing the de-N-acetylated and lactamized sialic acids have successfully carried out. By using the ~ synthesized ganglioside probes, the lactamized-sialyl 6-O-sulfo Lewis X was identified to be a major determinant recognized by G159 monoclonal antibody.
[2]A novel sulfated ganglioside GSC-338 designed from α-series hybrid-type ganglioside has been found to be a super-high affinity ligand of myelin-associated glycoprotein (MAG), a neural siglec 4a (Carbohydr.Res.,338,1621-1639,2003). It has also been found that GSC-338 is a potent inhibitor of CD38 NADase expressed on leukocytes (Bioorg.Med.Chem.Lett.,13,3441-3445,2003).
[3]The first total synthesis of α-(2-3)/α(2-6)-disialyl lactotetraosyl ceramide and disialyl Lewis X ganglioside as cancer-associated carbohydrate antigents has been carried out (Carbohydr. Res.,338,503-514,2003). The biosynthetic route and the expected functions were elucidated at the molecular level (J.Biol.Chem.,278,22787-22794,2003)

  • Research Products

    (120 results)

All Other

All Publications (120 results)

  • [Publications] Fukunaga, K.: "Synthesis of lacto- and neolacto-series ganglioside analogs containing N-glycolylneuraminic acid : probes for investigation of specific receptor structures recognized by influenza A viruses"J.Carbohydr.Chem.. 22. 919-937 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ishihara, A.: "Synthesis and selectin-blocking activity of a novel analog of sulfatide : 3-C-carboxymethylgalactosyl lipid."J.Carbohydr.Chem.. 22. 513-520 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yamaguchi, M.: "Studies on the endogenous L-selectin ligands : Systematic and highly efficient total synthetic routes to lactamized-sialyl 6-O-sulfo Lewis x and other novel gangliosides containing lactamized neuraminic acid."Carbohydr.Res.. 338. 2793-2812 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tamai, R.: "Cell activation by monosaccharide lipid A analogues utilizing Toll-like receptor 4."Immunology. 110. 66-72 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hara-Yokoyama, M.: "Novel sulfated gangliosides, high affinity ligands for neural siglecs, inhibit NADase activity of leukocyte cell surface antigen CD38."Bioorg.Med.Chem.Lett.. 13. 3441-3445 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hori, K.: "Synthetic study on Campylobacter jejuni lipopolysaccharides : an improved synthesis of a branched, heptose-containing trisaccharide core structure and its conversion into ganglioside GD3-related hexasaccharide."Eur.J.Org.Chem.. 3752-3760 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ando, H.: "Extending of the possibility of N-Troc-protected sialic acid donor toward variant sialoglycoside synthesis."Tetrahedron Lett.. 44. 6883-6886 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tsuchida, A.: "Synthesis of disialyl Lewis a (Lea) structure in colon cancer cell lines by a sialyltransferase, ST6GalNAc VI, responsible for the synthesis of a-series gangliosides."J.Biol.Chem.. 278. 22787-22794 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Imamura, A.: "Di-tert-butylsilylene (DTBS) group-directed a-selective galactosylation unaffected by C-2 participating functionalities."Tetrahedron Lett.. 44. 6725-6728 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito, H.: "Systematic synthesis and MAG-binding activity of novel sulfated GM1b analogues as the mimics of Chol-1 (a-series) gangliosides : highly active ligands for neural siglecs."Carbohydr.Res.. 338. 1621-1639 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ando, T.: "First total synthesis of a-(2-3)/a-(2-6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens."Carbohydr.Res.. 338. 503-514 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hamada, T.: "NMR structure elucidation of cyclic sialyl 6-sulfo Lewis x, a biologically dormant form of L-selectin ligand."Tetrahedron Lett.. 44. 1167-1170 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yamaguchi, M.: "Synthesis and selectin-binding activity of N-deacetylsialyl Lewis X ganglioside."Carbohydr.Res.. 337. 2111-2117 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Komori, T.: "A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo GM1b"Carbohydr.Res.. 337. 1679-1686 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Fukunaga, K.: "Synthesis of sialyl-a-(2-3)-neolactotetraose derivatives modified at C-2 of the N-acetylglucosamine residue : probes for investigation of acceptor specificity of human a-1,3-fucosyltransferases, Fuc-TVII and Fuc-TVII."Carbohydr.Chem.. 21. 385-409 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Matsuura, K.: "Selective expansion of the GM3 glycolipid monolayer induced by carbohydrate-carbohydrate interaction with Gg3 trisaccharide-bearing glycoconjugate polystyrene at the air-water interface"Langmur. 338. 6940-6945 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Otsubo, N.: "An efficient and straightforward synthesis of sialyl Le^x glycolipid as a potent selectin blocker."J.Carbohydr.Chem. 21(3). 247-255 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Galustian.C.: "Synergistic interactions of the two classes of ligand, sialyl -Lewis^a/^x fuco-oligosaccharides and short sulpho-motifs, with the P- and L-selectins : implications for therapeutic inhibitor designs."Immunology. 105. 350-359 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hamada, T.: "NMR analysis of novel ganglioside GM4 analogues containing de-N-acetyl and lactamized sialic acid : probes for searching new ligand structures for human L-selectin."Magn.Reson.Chem.. 40. 517-523 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takashima, S.: "Molecular cloning and expression of a sixth type of a2,8-sialyltransferase (ST8Sia VI) that sialylates O-glycans."J.Biol.Chem.. 277. 24030-24038 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Schnaar, R.L.: "Immunoglobulin G-class mouse monoclonal antibody to major brain gangliosides."Anal.Biochem. 302. 276-284 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Brandenburg, K: "Biophysical characterization of triacyl monosaccharide lipid A partial structures in relation to bioactivity"Biophysical J.. 83. 322-333 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Otsubo, N.: "Total Synthesis of O-Glycan on the L-selectin lingand GlyCAM-1."Aust.J.Chem.. 55. 105-112 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kita, K.: "Activation of bacterial ceramidase by anioinc glycorophospholipids : possible involvement in ceramide hydrolysis on atopic skin by Pseudomonas ceramidase."Biochem.J.. 362. 619-626 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ariga, T.: "Gangliosides inhibit the release of interleukin-1b in amyloid b-protein-treated human monocytic cells."J.Molecular Neuroscience. 17. 371-377 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito, H.: "A highly efficient total synthetic route to α-series gangliosides : GM1α, GD1α and GT1α."J.Carbohydr.Chem.. 20(2). 207-225 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Otsubo, N.: "The first, efficient synthesis of novel sLe^x neoglycolipids containing N-deacetylated and lactamized sialic acid : key ligand structures for selectin binding."Carbohydr.Res.. 330(1). 1-5 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ariga, T.: "Characterization of high-affinity binding between gangliosides and amyloid β-protein"Archiv.Biochem.Biophys. 388. 225-230 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Sawada, N.: "The first synthesis of glycan parts of lactoganglio- and neolactoganglio-series gangliosides."Tetrahedron Lett.. 42. 1745-1747 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Komba, S.: "6-O-Sulfo de-N-acetylsialyl Lewis x as a novel high-affinity ligand for human L-selectin : total synthesis and structural characterization"Biol.Chem.. 382. 233-240 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Furui, H.: "Synthesis of sialyl- and sulfo-Le^x/Le^a analogs containing N-alkyl-1-deoxynojirimycin as potential selectin blockers"J.Carbohydr.Chem.. 20(9). 789-812 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ando, T.: "highly efficient synthetic route to a(2-3) / a(2-6) disialyl Lewis a as a cancer associated carbohydrate antigen"J.Carbohydr.Chem.. 20(5). 425-430 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Fotinou, C.: "The crystal structure of tetanus toxin Hc fragment complexed with a synthetic GT1b analogue suggests cross-linking between ganglioside receptors and the toxin"J.Biol.Chem.. 276. 32274-32281 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Mamelak, D.: "The aglycone of sulfogalactolipids can alter the sulfate ester substitution position required for hsc70 recognition."Carbohydr.Res.. 20. 91-100 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Otsubo, N.: "The first, efficient synthesis of novel sLe^x neoglycolipids containing N-deacetylated and lactamized sialic acid : key ligand structures for selectin binding"J.Carbohydr.Chem.. 20. 329-334 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ito, T.: "Recognition of N-glycolylneuraminic acid linked to galactose by the α2,3 linkage is associated with the intestinal replication of influenza A virus in ducks"J.Virol.. 74. 9300-9305 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Suzuki, Y.: "Sialic acid species as a determinant of the host range of influenza A viruses"J.Virol.. 74. 11825-11831 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Matsuura, K.: "A quantitative estimation of carbohydrate-carbohydrate interaction using clustered oligosaccharides of glycolipid monoalayers and of arifical glycocomjugate polymers by surface plasmon resonance."J.Am.Chem.Soc.. 122. 7406-7407 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hubi, U.: "Studies on the specificity and sensitivity of the influeneza C virus binding assay for 9-O-acetylated sialic acids and its application to human melanomas."J.Biochem.. 127. 1021-1031 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Otsubo, N.: "The first, highly efficient synthesis of spacer-armed O-glycans on GlyCAM-1 and PSGL-1 : the counter-receptors for L- and P-selectin"Tetrahedron Lett.. 41. 3879-3882 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Okajima, T.: "Molecular cloning and expression of mouse GD1a/GT1aα/GQ1bα synthase (ST6GalNAc VI) gene"J.Biol.Chem.. 275. 6717-6723 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Tanahashi, E.: "Synthesis of sialyl-α-(2→3)-neolactotetraose derivatives containing different sialic acids : molecular probes for elucidation of substrate specificity of human α1,3-fucosyltransferases"J.Carbohydr.Chem.. 19. 747-776 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Fukunaga, K.: "Systematic synthesis of sulfated sialyl-α(2-3)-neolactotetraose derivatives and their acceptor specificity for a α1,3-fucosyltransferase (Fuc-TVII) involved in the biosynthesis of L-selectin ligand"Carbohydr.Res.. 328. 85-94 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 木曽 真: "生理活性シアロ糖鎖の構造と機能に関する化学生物学的研究"日本農芸化学会誌. 76. 1158-1167 (2002)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ando, T.: "Sialic acid and glycobiology : a chemical approach"TIGG. 13. 573-586 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 木曽 真: "白血球、リンパ球の表面で働く分子"化学と教育. 49(7). 411-413 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 木曽 真: "ガングリオシドプローブを用いて糖鎖の多彩な機能を探る"化学と生物. 39(7). 454-463 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ishida, H.: "Systematic syntheses of gangliosides"TIGG. 13. 57-64 (2001)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 木曽 真: "健康と生命化学"日本農芸化学会誌. 74. 781-782 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ishida, H.: "Synthetic study on neural siglecs ligands : systematic synthesis of α-series polysialogangliosides and their analogues"J.Synth.Org.Chem., Jpn. 58. 1108-1113 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 石田秀治: "コールドスプリングハーバー 糖鎖生物学"丸善. 527 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 石田秀治: "糖鎖工学・設計酵素による糖鎖合成"農芸化学の事典""朝倉書店. 287-294 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kiso, M.: "Complex Carbohydrate Synthesis, in Carbohydrate-based Drug Discovey"Wiley-VCH. 37-54 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 木曽 真: "創薬のシーズを糖鎖に求めて"先端化学シリーズIII 糖鎖/バイオマテリアル/分子認識/バイオインフォマティクス""丸善. 14-19 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ando, H.: "Synthesis of sialic acid containing carbohydrates, in Carbohydrates"Academic Press. 277-310 (2003)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Kiso, M.: "Special problems in glycosylation reactions : Sialidations, in Carbohydrates in Chemistry and Biology, vol.I"Wiley-VCH. 345-365 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 石田秀治: "含硫シアル酸アナログの化学と応用"複合糖質の化学""シーエムシー. 50-63 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ishida, H.: "Glycolipid synthesis, in Carbohydrates in Chemistry and Biology, vol.I"Wiley-VCH. (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 長谷川 明: "S-グリコシド合成;生物薬科学実験講座、脂質II-2"廣川書店. 266-270 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Ikami, T.: "Synthesis and biological activity of glycolipids, with a focus on gangliosides and sulfatide analogs, in Sphingolipid Metabolism and Cell Signaling Part A"Academic Press. 547-568 (2000)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Fukunaga, K., Toyoda, T., Ishida, H., Kiso, M.: "Synthesis of lacto-and neolacto-series ganglioside analogs containing N-glycolylneuraminic acid : probes for investigation of specific receptor structures recognized by influenza A viruses."J.Carbohydr.Chem.. 22. 919-937 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishihara, A., Ishida, H., Ikami, T., Tomiya, N., Ando, H., Kiso, M.: "Synthesis and selectin-blocking activity of a novel analog of sulfatide : 3-C-carboxymethylgalactosyl lipid."J.Carbohydr.Chem.. 22. 513-520 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yamaguchi, M., Ishida, H., Kanamori, A., Kannagi, R., Kiso, M.: "Studies on the endogenous L-selectin ligands : Systematic and highly efficient total synthetic routes to lactamized-sialyl 6-O-sulfo Lewis x and other novel gangliosides containing lactamized neuraminic acid."Carbohydr.Res.. 338. 2793-2812 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tamai, R., Asai, Y., Hashimoto, M., Fukase, K., Kusumoto, S., Ishida, H., Kiso, M., Ogawa, T.: "Cell activation by monosaccharide lipid A analogues utilizing Toll-like receptor 4."Immunology. 110. 66-72 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hara-Yokoyama, M., Ito, H., Ueno-Noto, K., Takano, K., Ishida, H., Kiso, M.: "Novel sulfated gangliosides, high affinity ligands for neural siglecs, inhibit NADase activity of leukocyte cell surface antigen CD38."Bioorg.Med.Chem.Lett.. 13. 3441-3445 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hori, K., Sawada, N., Ando, H., Ishida, H., Kiso, M.: "Synthetic study on Campylobacter jejuni lipopolysaccharides : an improved synthesis of a branched, heptose-containing trisaccharide core structure and its conversion into ganglioside GD3-related hexasaccharide."Eur.J.Org.Chem.. 3752-3760 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ando, H., Koike, Y., Ishida, H., Kiso, M.: "Extending of the possibility of N-Troc-protected sialic acid donor toward variant sialo-glycoside synthesis."Tetrahedron Lett.. 44. 6883-6886 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tsuchida, A., Okajima, T., Furukawa, K., Ando, T., Ishida, H., Yoshida, A., Nakamura, Y., Kannagi, R., Kiso, M., Furukawa, K.: "Synthesis of disialyl Lewis a (Lea) structure in colon cancer cell lines by a sialyltransferase, ST6GalNAc VI, responsible for the synthesis of α-series gangliosides."J.Biol.Chem.. 278. 22787-22794 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Imamura, A., Ando, H., Korogi, S., Tanabe, G., Muraoka, O., Ishida, H., Kiso, M.: "Di-tert-butylsilylene (DTBS) group-directed a-selective galactosylation unaffected by C-2 participating functionalities."Tetrahedron Lett.. 44. 6725-6728 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H., Ishida, H., Collins, B.E., Fromholt, S.E., Schnaar, R.L., Kiso, M.: "Systematic synthesis and MAG-binding activity of novel sulfated GM1b analogues as the mimics of Chol-1 (α-series) gangliosides : highly active ligands for neural siglecs."Carbohydr.Res.. 338. 1621-1639 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ando, T., Ishida, H., Kiso, M.: "First total synthesis of α-(2→3)/α-(2→6)-disialyl lactotetraosyl ceramide and disialyl Lewis A ganglioside as cancer-associated carbohydrate antigens."Carbohydr.Res.. 338. 503-514 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hamada, T., Hirota, H., Yokoyama, S., Yamaguchi, M., Otsubo, N., Ishida, H., Kiso, M., Kanamori, A., Kannagi, R.: "NMR structure elucidation of cyclic sialyl 6-sulfo Lewis x, a biologically dormant form of L-selectin ligand."Tetrahedron Lett.. 44. 1167-1170 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yamaguchi, M., Ishida, H., Galustian, C., Feizi, T., Kiso, M.: "Synthesis and selectin-binding activity of N-deacetylsialyl Lewis X ganglioside."Carbohydr.Res.. 337. 2111-2117 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Komori, T., Kondo, S., Ando, H., Ishida, H., Kiso, M.: "A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo GM1b."J.Carbohydr.Chem.. 21. 385-409 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fukunaga, K., Ikami, N., Ishida, H., Kiso, M.: "Synthesis sialyl-α-(2→3)-neolactotetraose derivatives modified at C-2 of the N-acetylglucosamine residue : probes for investigation of acceptor specificity of human α-1,3-fucosyltransferases, Fuc-TVII and Fuc-TVII."J.Carbohydr.Chem.. 21. 385-409 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Matsuura, K., Kitakouji, H., Oda, R., Morimoto, Y., H., A., Ishida, H., Kiso, M., Kitajima, K., Kobayashi, K.: "Selective expansion of the GM3 glycolipid monolayer induced by carbohydrate-carbohydrate interaction with Gg3 trisaccharide-bearing glycoconjugate polystyrene at the air-water interface."Langmur. 18. 6940-6945 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Otsubo, N., Ishida, H., Kiso, M.: "An efficient and straightforward synthesis of sialyl Le^x glycolipid as a potent selectin blocker."J.Carbohydr.Chem.. 21(3). 247-255 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Galustian, C., Childs, R.A., Stoll, M., Ishida, H., Kiso, M., Feizi, T.: "Synergistic interactions of the two classes of ligand, sialyl-Lewis^<a/x> fuco-oligosaccharides and short sulpho-motifs, with the P-and L-selectins : implications for therapeutic inhibitor desingns."Immunology. 105. 350-359 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hamada, T., Hirota, H., Yokoyama, S., Otsubo, N., Ishida, H., Kiso, M., Kanamori, A., Kannagi, R.: "NMR analysis of novel ganglioside GM4 analogues containing de-N-acetyl and lactamized sialic acid : probes for searching new ligand structures for human L-selectin."Magn.Reson.Chem.. 40. 517-523 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Takashima, S., Ishida, H.-K., Inazu, T., Ando, T., Ishida, H., Kiso, M., Tsuji, S., Tsujimoto, M.: "Molecular cloning and expression of a sixth type of α2,8-sialyltransferase (ST8Sia VI) that sialylates O-glycans."J.Biol.Chem.. 277. 24030-24038 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Schnaar, R.L., Fromholt, S.E., Gong, Y., Vyas, A.A., Laroy, W., Wayman, D.M., Heffer-Lauc, H., Ito, H., Ishida, H., Kiso, M., Griffin, J.W., Shiekh, K.: "Immunoglobulin G-class mouse monoclonal antibody to major brain gangliosides."Anal.Biochem.. 302. 276-284 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Brandenburg, K., Matsuura, M., Heine, H., Muller, M., Kiso, M., Ishida, H., Koch, M.H.J., Seydel, U.: "Biophysical characterization of triacyl monosaccharide lipid A partial structures in relation to bioactivity."Biophysical J.. 83. 322-333 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Otsubo, N., Ishida, H., Kiso, M.: "Total Synthesis of O-Glycan on the L-selectin lingand GlyCAM-1."Aust.J.Chem.. 55. 105-112 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kita, K., Sueyoshi, N., Okino, N., Inagaki, M., Ishida, H., Kiso, M., imayama, S., Nakamura, T., Ito, M.: "Activation of bacterial ceramidase by anioinc glycorophospholipids : possible involvement in ceramide hydrolysis on atopic skin by Pseudomonas ceramidase."Biochem.J.. 362. 619-626 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ariga, T., Kiso, M., Hasegawa, A., Miyatake, T.: "Gangliosides inhibit the release of interleukin-1β in amyloid β-protein-treated human monocytic cells."J. Molecular Neuroscience. 17. 371-377 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Furui, H., Ando-Furui, K., Inagaki, H., Ando, T., Ishida, H., Kiso, M.: "Synthesis of sialyl-and sulfo-Le^x/Le^a analogs containing N-alkyl-1-deoxynojirimycin as potential selectin blockers."J.Carbohydr.Chem.. 20(9). 789-812 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ando, T., Ishida, H., Kiso, M.: "A highly efficient synthetic route to α(2-3)/α(2-6) disialyl Lewis a as a cancer associated carbohydrate antigen."J.Carbohydr.Chem.. 20(5). 425-430 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fotinou, C., Emsly, P., Black, I., Ando, H., Ishida, H., Kiso, M., Sinha, K.A., Fairweather, N.F., Isaacs, N.W.: "The crystal structure of tetanus toxin Hc fragment complexed with a synthetic GT1b analogue suggests cross-linking between ganglioside receptors and the toxin."J.Biol.Chem.. 276. 32274-32281 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Mamelak, D., Mylvaganam, M., Tanahashi, E., Ito, H., Ishida, H., Kiso, M., Lingwood, C.: "The aglycone of sulfogalactolipids can alter the sulfate ester substitution position required for hsc70 recongnition."Carbohydr.Res.. 335. 91-100 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Otsubo, N., Yamaguchi, M., Ishida, H., Kiso, M.: "The first, efficient synthesis of novel sLe^x neoglycolipids containing N-deacetylated and lactamized sialic acid : key ligand structures for selectin binding."J.Carbohydr.Chem.. 20. 329-334 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, H., Ishida, H., Kiso, M.: "A highly efficient total synthetic route to α-series gangliosides : GM1 α, GD1 α and GT1 α."J.Carbohydr.Chem.. 20(2). 207-225 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Otsubo, N., Ishida, H., Kiso, M.: "Synthesis of novel ganglioside GM4 analogues containing N-deacetylated and lactamized sialic acid : probes for searching new ligand structures for human L-selectin."Carbohydr.Res.. 330(1). 1-5 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ariga, T., Kobayashi, K., Hasegawa, A., Kiso, M., Ishida, H., Miyake, T.: "Characterization of high-affinity binding between gangliosides and anyloid β-protein."Archiv.Biochem.Biophys.. 388. 225-230 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Sawada, N., Ito, M., Ishida, H., Kiso, M.: "The first synthesis of glycan parts of lactoganglio-and neolactoganglio-series gangliosides."Tetrahedron Lett.. 42. 1745-1747 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Komba, S., Yamaguchi, M., Ishida, H., Kiso, M.: "6-O-Sulfo de-N-acetylsialyl Lewis x as a novel high-affinity ligand for human L-selectin : total synthesis and structural characterization."Biol.Chem.. 382. 233-240 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ito, T., Suzuki, Y., Suzuki, T., Takada, A., Horimoto, T., Wells, K., Kida, H., Otsuki, K., Kiso, M., Ishida, H., Kawaoka, Y.: "Recognition of N-glycolylneuraminic acid linked to galactose by the α2,3 linkage is associated with the intestinal replication of influenza A virus in ducks."J.Virol.. 74. 9300-9305 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Suzuki, Y., Ito, T., Suzuki, T., Holland, R.E., Chambers, T.M., Kiso, M., Ishida, H., Kawaoka, Y.: "Sialic acid species as a determinant of the host range of influenza A viruses."J.Virol.. 74. 11825-11831 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Matsuura, K., Kitakouji, H., Sawada, N., Ishida, H., Kiso, M., Kitajima, K., Kobayashi, K.: "A quantitative estimation of carbohydrate-carbohydrate interaction using clustered oligosaccharides of glycolipid monoalayers and of arifical glycocomjugate polymers by surface plasmon resonance."J.Am.Chem.Soc.. 122. 7406-7407 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hubi, U., Ishida, H., Kiso, M., Hasegawa, A., Schauer, R.: "Studies on the specificity and sensitivity of the influeneza C virus binding assayfor 9-O-acetylated sialic acids and its application to human melanomas."J.Biochem.. 127. 1021-1031 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Otsubo, N., Ishida, H., Kiso, M.: "The first, highly efficient synthesis of spacer-armed O-glycans on GlyCAM-1 and PSGL-1 : the counter-receptors for L-and P-selectin."Tetrahedron Lett.. 41. 3879-3882 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Okajima, T., Chen, H.-H., Ito, H., Kiso, M., Tai, T., Furukawa, K., urano, T., Furukawa, K.: "Molecular cloning and expression of mouse GD1α/GT1aα/GQ1bα synthase (ST6Ga1NAc VI) gene."J.Biol.Chem.. 275. 6717-6723 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Tanahashi, E., Fukunaga, K., Ozawa, Y., Toyoda, T., Ishida, H., Kiso, M.: "Synthesis of sialyl-α-(2→3)-neolactotetraose derivatives containing different sialic acids : molecular probes for elucidation of substrate specificity of human α1,3-fucosyltransferases."J.Carbohydr.Chem.. 19. 747-768 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Fukunaga, K., Shinoda, K., Ishida, H., Kiso, M.: "Systematic synthesis of sulfated sialyl-α(2-3)-neolactotetraose derivatives and their acceptor specificity for a α1,3-fucosyltransferase (Fuc-TVII) involved in the biosynthesis of L-selectin ligand."Carbohydr.Res.. 328. 85-94 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M.: "Chemical biology on the structure and function of bio-active sialo-oligosaccharides (in Japanese)."Nippon Nougeikagaku Kaishi. 76. 1158-1167 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ando, T., Ando, H., Kiso, M.: "Sialic acid and glycobiology : a chemical approach."TIGG. 13. 573-586 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M.: "Molecules functioning on the structure of leukocyte and lymphocyte (in Japanese)."Kagaku to Kyoiku. 49(7). 411-413 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M., Ishida, H.: "Elucidation of a variety of functions of oligosaccharide using ganglioside probes (in Japanese)."Kagaku to Seibutsu. 39(7). 454-463 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Kiso, M.: "Systematic syntheses of gangliosides."TIGG. 13. 57-64 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M.: "Health and life chemistry (in Japanese)."Nippon Nougeikagaku Kaishi. 74. 781-782 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Kiso, M.: "Synthetic study on neural siglecs ligands : systematic synthesis of α-series polysialogangliosides and their analogues."J.Synth.Org.Chem., Jpn.. 58. 1108-1113 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Ikekita, M., Kakehi, K., Kiso, M., Kitajima, K., Kimata, K., Furukawa, K., Horido, S., Miyasaka, M.: "Cold Spring Harbor Glycobiology (in Japanese)"Maruzen、Tokyo. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Kiso, M.: "Glycoenginearing : Oligosaccharide synthesis by designed enzymes "Nogeikagaku no Jiten"(in Japanese)"Asakura、Tokyo. 287-294 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M., Ishida, H., Ando, H.: "Complex Carbohydrate Synthesis, in Carbohydrate-based Drug Discovery"Wiley-VCH. 37-54 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M.: "Oligosaccharides as seeds of drug production (in Japanese)"Sentankagaku III oligosaccharide/biomaterial/molecular recognition/bioinformatics"Maruzen、Tokyo. 14-19 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ando, H., Ishida, H., Kiso, M.: "Synthesis of sialic acid containing carbohydrates, in Carbohydrates"Academic Press. 277-310 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Kiso, M., Hasegawa, A.: "Synthesis and application of sialic acid analogs containing sulfur "Fukugoutoushitsu no Kagaku"(in Japanese)"CMC. 50-63 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Kiso, M., Ishida, H., Ito, H.: "Special problems in glycosylation reactions : Sialidations, in Carbohydrates in Chemistry and Biology"vol.I, Wiley-VCH. 345-365 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ishida, H., Kiso, M.: "Glycolipid synthesis, in Carbohydrates in Chemistry and Biology"vol.I, Wiley-VCH. (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Hasegawa, A., Kiso, M., Ishida, H.: "Synthesis of S-glycoside ; Seibutsu Yakugaku Jikken Kouza, Shishitsu II-2 (in Japanese)"Hirokawa、Tokyo. 266-270 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Ikami, T., Ishida, H., Kiso, M.: "Synthesis and biological activity of glycolipids, with a focus on gangliosides and sulfatide analogs, in Sphingolipid Metabolism and Cell Signaling Part A."Academic Press. 547-568 (2000)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 2005-04-19  

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