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1989 Fiscal Year Final Research Report Summary

Studies on the Glycolipid from an Invertebrate Animal

Research Project

Project/Area Number 63571002
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNAGOYA CITY UNIVERSITY

Principal Investigator

TAKEDA Tadahiro  Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Nagoya City University, 薬学部, 助教授 (90106253)

Project Period (FY) 1988 – 1989
KeywordsInvertebrate animal / Glycolipid / Hyriopsis schlegelii / Octasaccharide / Glycosidation / Fertilization mechanism / Cell surface glycans / Condensation
Research Abstract

The glycosphingolipids isolated from spermatozoa of a fresh-water bivalve, Hyriopsis schlegelii, have a unique structure containing one or two mannosyl residues, novel linkages including an internal fucopyranosyl residue, as well as terminal xylosyl and 4-0-methyl-D-glucopyranosyluronic acid groups. The trisaccharide depends on non-reducing end and the pentasaccharide derivative depends on reducing end, that constitute the partial structure of lipid IV were synthesized as follows. Condensation of 4,6-di-0-acetyl-2-azido-2-deoxy-3-0-methyl-alpha-D-galacto-pyranosyl bromide with 2-(trimethylsilyl)ethyl 4-0-acetyl-2-0-benzyl-beta-L-fuco-pyranoside, in the presence of mercuric cyanide, gave the corresponding disaccharide. Condensation of methy(2,3-di-0-acetyl-4-0-methyl-alpha-D-glucopyranosyl bromide)uronate with the appropriate OH-4-free disaccharide derivative afforded 2-(trimethylsilyl) ethyl 2-0-benzyl-3-0-(4,6-di-0-acetyl-2-azido-2-deoxy-3-0-methyl-alpha-D-galactopyranosyl)-4-0-[methyl(2,3-di-0-acetyl-4-0-methyl-beta-D-glucopyranosyl)uronate]-beta-L-fucopyranoside.
Meanwhile, in the case of the blockwise synthesis of pentasaccharide, 4,6-di-0-acetyl-2-0-(2,3,4-tri-0-acetyl-beta-D-xylopyranosyl)-3-0-benzyl-alpha-D-mannopyranosyl bromide was treated with 2,3-di-0-acetyl-1,6-anhydro-beta-D-glucopyranose in the presence of silver zeolite to afford the corresponding trisaccharide, 2,3-di-0-acetyl-4-0-[4,6-di-0-acetyl-3-0-benzyl-2-0-(2,3,4-tri-0-acetyl-beta-D-xylopyranosyl)-alpha- and -beta-D-mannopyranosyl]-1,6-anhydro-beta-D-glucopyranose. beta-Glycosidation took precedence. After debenzylation, trisaccharide derivative was condensed with mannose derivative, and the final pentasaccharide derivative was prepared by using a suitably protected tetrasaccharide and 3-0-acetyl-6-0-benzyl-4-0-chloroacetyl-2-phthalimido-2-deoxy-beta-D-glucopyranosyl bromide as the glycosyl donor, and silver triflate as the promoter.

  • Research Products

    (8 results)

All Other

All Publications (8 results)

  • [Publications] Osamu Kanie: "Synthesis of a precursor of 3-O-(2-acetamido-2-deoxy-3-O-methyl-α-D-galactopyranosyl)-4-O-(4-O-methyl-β-D-glucopyranosyl uronic acid)-L-fucose" Carbohydrate Redsearch. 190. 53-64 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Osamu Kanie: "The crystal and molecular structure of methyl(1R)-1,2,3,5-tetra-O-acetyl-4-O-methyl-D-glucuronate methyl acetal" Carbohydrate Research. 193. 271-274 (1989)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Osamu Kanie: "Acetolysis of methyl(methyl 4-O-methyl-β-D-glucopyranosid)uronate" Carbohydrate Research. 196. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Osamu Kanie: "A convenient synthesis of 2,3-di-O-acetyl-1,6-anhydro-β-D-glucopyranose" J.Carbohydrate Chemistry. 9. (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] O. Kanie: "Synthesis of a precursor of 3-O-(2-acetamido-2-deoxy-3-O-methyl-alpha-D-galactopyranosyl)-4-O-(4-O-methyl-beta-D-glucopyranosyl uronic acid)-L-fucose" Carbohydr. Res., 190, 53-64 (1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] O. Kanie: "The crystal and molecular structure of methyl(1R)-1,2,3,5-tetra-O-acetyl-4-O-methyl-D-glucuronate methyl acetal" Carbohydr. Res., 193, 271-274(1989).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] O. Kanie: "Acetolysis of methyl(methyl 4-O-methyl-beta-D-glucopyranosid)uronate" Carbohydr. Res., 196, (1990).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] O. Kanie: "A convenient synthesis of 2,3-di-O-acetyl-1,6-anhydro-beta-D-glucopyranose" J. Carbohydr. Chem., 9, (1990).

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

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Published: 1993-03-26  

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