Establishment of general procedure to synthesize polysialogangliosides and its application for neurobidogy.

• Project/Area Number: 16580086
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Bioproduction chemistry/Bioorganic chemistry
• Research Institution: Gifu University
• Principal Investigator: ISHIDA Hideharu Gifu University, Faculty of Biological Science, Professor, 応用生物科学部, 教授 (20203002)
• Project Period (FY): 2004 – 2005
• Project Status: Completed (Fiscal Year 2005)
• Budget Amount: ¥3,700,000 (Direct Cost: ¥3,700,000); Fiscal Year 2005: ¥1,800,000 (Direct Cost: ¥1,800,000); Fiscal Year 2004: ¥1,900,000 (Direct Cost: ¥1,900,000)
• Keywords: ganglioside / sialic acid / ceramide / sphingo-glycolipid

Research Abstract

Glycosphingolipids are characteristic membrane components of eukaryotic cells where they are distinguished from other glycosphingolipids by containing one or more sialic acid residues, and have been recognized play important roles in many biological processes, particularly in nervous system We have succeeded in the establishment of general procedunes to synthesize polysialogangliosides. The achievements are summarized in the following two parts.
1.Efficient construction of polysialo-oligosaccharides.
α(2-4)- and α(2-8)disialic acid seguences were obtained in high yields by employing 1,5-lactamized sialyl acceptors. The disaccharides obtained were utilized for the construction of sialo-oligosaccharides.
2.The coupling of oligosaccharides and ceramides by intramolecular-aglycon derivery.
Tethering of ceramide to glucose, reducing terminal of oligosaccharides, with succnic acid allowed the efficient coupling of oligosaccharides and ceramides. The glucosyl ceramide obtained was further glycosylated with sialo-oligosaccharides as building bloks to give the desired gangliosides.

Research Products

• [Journal Article] シアル酸分子多様性を網羅する糖鎖合成法の開拓-シアロ糖鎖多機能性の分子理解を目指して- (2006)
  • Author(s): 安藤弘宗
  • Journal Title: 有機合成化学協会誌 64(5) Pages: 481-491
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Studies on the α-(1→4)- and α-(1→8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides (2006)
  • Author(s): Ando, H.
  • Journal Title: Carbohydrate Research 341 Pages: 1522-1532
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Synthesis and enzymatic susceptibility of a series of novel GM2 analogs (2006)
  • Author(s): Fuse, T.
  • Journal Title: Glycoconjugate Journal 23 Pages: 329-343
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Study on the Method for Oligosaccharide Synthesis Covering the Structural Diversity of Sialic Acid- Aiming at the Understanding of the Polymorphous Functions at the Molecular Level- (2006)
  • Author(s): Ando, H.Ishida H.Kiso, M.
  • Journal Title: Journal of Synthetic Organic Chemistry, JAPAN 64(5) Pages: 481-491
  • NAID: 10017486696
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Studies on the α-(1→4)-and α-(1→8)-fucosylation of sialic acid for the total assembly of the glycan portions of complex HPG-series gangliosides (2006)
  • Author(s): Ando, H., Shimizu, H., Katano, Y., Koike, Y., Koizumi, S., Ishida, H., Kiso, M.
  • Journal Title: Carbohydrate Research 341 Pages: 1522-1532
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Ando T. : Synthesis and enzymatic susceptibility of a series of novel GM2 analogs (2006)
  • Author(s): Fuse, T., Ando, H., Imamura, A., Sawada, N., Ishida H., kiso, M.
  • Journal Title: Glycoconjugate Journal 23 Pages: 329-343
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] 6-0-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid : synthesis and antigenic reactivity against G159 monoclonal antibody (2005)
  • Author(s): Yamaguchi, M.
  • Journal Title: Glycoconjugate Journal 22 Pages: 95-108
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Design and synthesis of a novel neo-glycolipid containing sialyl Lewsi X determinant carried on the mucin GlcNAcb1-6GalNAca core structure (2005)
  • Author(s): Otsubo, N.
  • Journal Title: Tetrahedron : Asymmetry 16(7) Pages: 1321-1327
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] 1,5-Lactamized sialyl acceptors for various disialoside syntheses : Novel synthesis method for glycan portions of Hp-s6 and HLG-2 gangliosides (2005)
  • Author(s): Ando, H.
  • Journal Title: Angewandte Chemie,International Edition in English Pages: 6759-6763
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] Di-tert-butylsilylene(DTBS)-directed a-selective synthesis of 4-methylumbelliferyl T-antigen (2005)
  • Author(s): Imamura, A.
  • Journal Title: Organic Letters 7(20) Pages: 4415-4418
  • Description: 「研究成果報告書概要(和文)」より
• [Journal Article] 6-O-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid : synthesis and antigenic reactivity against G159 monoclonal antibody (2005)
  • Author(s): Yamaguchi, M., Ishida, H., Kanamori, A., Kannagi, R., Kiso, M.
  • Journal Title: Glycoconjugate Journal 22 Pages: 95-108
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Design and synthesis of a novel neo-glycolipid containing sialyl Lewis X determinant carried on the mucin GlcNAcb1-6GalNAca core structure (2005)
  • Author(s): Otsubo, N., Ishida, H., Kannagi, R., Kiso, M.
  • Journal Title: Tetrahedron : Asymmetry 16(7) Pages: 1321-1327
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] 1,5-Lactamized sialyl acceptors for various disialoside syntheses : Novel synthesis method for glycan portions of Hp-s6 and HLG-2 gangliosides (2005)
  • Author(s): Ando, H., Koike, Y., Koizumi, S., Ishida, H., Kiso, M.
  • Journal Title: Angewandte Chemie, International Edition in English Pages: 6759-6763
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] Di-tert-butylsilylene(DTBS)-directed a-selective synthesis of 4-methylumbelliferyl T-antigen. (2005)
  • Author(s): Imamura, A., Ando, H., Ishida, H., Kiso, M.
  • Journal Title: Organic Letters 7(20) Pages: 4415-4418
  • Description: 「研究成果報告書概要(欧文)」より
• [Journal Article] 6-O-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid : synthesis and antigenic reactivity against G 159 monoclonal antibody (2005)
  • Author(s): Yamaguchi, M.
  • Journal Title: Glycoconjugate Journal 22 Pages: 95-108
• [Journal Article] Design and synthesis of a novel neo-glycolipid containinc sialyl Lewis X determinant carried on the mucin GlcNAcb1-6GalNAca core structure (2005)
  • Author(s): Otsubo, N.
  • Journal Title: Tetrahedron : Asymmetry 16(7) Pages: 1321-1327
• [Journal Article] 1,5-Lactamized sialyl acceptors for various disialoside syntheses : Novel synthesis method for glycan portions of Hp-s6 and HLG-2 gangliosides (2005)
  • Author(s): Ando, H.
  • Journal Title: Angewandte Chemie, International Edition in English Pages: 6759-6763
• [Journal Article] 6-O-Sulfo sialylparagloboside and sialyl Lewis X neo-glycolipids containing lactamized neuraminic acid : synthesis and antigenic reactivity against G159 monoclonal antibody (2005)
  • Author(s): Yamaguchi, M., Ishida, H., Kanamori, A., Kannagi, R., Kiso, M.
  • Journal Title: Glycoconjugate J. (印刷中)
• [Journal Article] Design and synthesis of a novel neo-glycolipid containing sialyl Lewis X determinant carried on the mucin GlcNAcbl-6GalNAca core structure (2005)
  • Author(s): Otsubo, N., Ishida, H., Kannagi, R., Kiso, M.
  • Journal Title: Tetrahedron Asymmetry. (印刷中)
• [Journal Article] Surface plasmon resonance study of carbohydrate-carbohydrate interaction between various gangliosides and Gg3-carring polystyrene (2004)
  • Author(s): Matsuura, K., Oda, R., Kitakouji, H., Kiso, M., Kitajima, K., Kobayashi, K.
  • Journal Title: Biomacromolecules 5 Pages: 937-941
• [Journal Article] Loss of disialyl Lewis^a, the ligand for lymphocyte inhibitor receptor sialic acid-binding immunoglobulin-like lectin-7 (siglec-7) associated with increased sialyl Lewis^a expression on human colon cancers (2004)
  • Author(s): Miyazaki, K., Ohmori.K., Izawa, M., Koike, T., Kumamoto, K., Furukawa, K., Ando, T., Kiso, M., Yamaji, T., Hashimoto.Y., Suzuki, A., Yoshida, A., Takeuchi, M, Kannagi, R
  • Journal Title: Cancer Res. 64 Pages: 4498-4505
• [Journal Article] Synthesis and antigenic property of a novel sialyl 6-O-sulfo Lewis x neo-glycolipid containing lactamized neuraminic acid (2004)
  • Author(s): Yamaguchi, M., Ishida, H., Kanamori, A., Kannagi, R., Kiso, M.
  • Journal Title: J.Carbohydr.Chem. 23 Pages: 201-215
• [Book] 糖鎖化学の最先端技術 The Recent Trends of Glycochemistry (2005)
  • Author(s): 石田 秀治
  • Total Pages: 318
  • Publisher: シーエムシー出版
  • Description: 「研究成果報告書概要(和文)」より
• [Book] 未来を拓く 糖鎖化学 (2005)
  • Author(s): 石田 秀治
  • Total Pages: 467
  • Publisher: (株)金芳堂
  • Description: 「研究成果報告書概要(和文)」より
• [Book] 糖鎖科学の新展開 (2005)
  • Author(s): 安藤 弘宗
  • Total Pages: 536
  • Publisher: (株)エヌ・ティ・エス
  • Description: 「研究成果報告書概要(和文)」より
• [Book] 糖類化学の最先端技術 The Recent Trends of Glycochemistry (2005)
  • Author(s): 石田 秀治
  • Total Pages: 318
  • Publisher: シーエムシー出版
• [Book] 未来を拓く 糖鎖科学 (2005)
  • Author(s): 石田 秀治
  • Total Pages: 467
  • Publisher: (株)金芳堂
• [Patent(Industrial Property Rights)] スフィンゴ糖脂質のケミカル合成法 (2007)
  • Inventor(s): 石田ら
  • Industrial Property Rights Holder: 岐阜大学
  • Industrial Property Number: 2007-031355
  • Filing Date: 2007-02-09
  • Description: 「研究成果報告書概要(和文)」より