Synthesis of alpha- and beta-linked tyvelose epitopes of the Trichinella spiralis glycan: 2-acetamido-2-deoxy-3-O-(3,6-dideoxy-D-arabino-hexopyranosyl)-beta -D-galactopyranosides.

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  • Author(s): Probert MA;Probert MA; Zhang J; Bundle DR
  • Source:
    Carbohydrate research [Carbohydr Res] 1996 Dec 24; Vol. 296, pp. 149-70.
  • Publication Type:
    Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S.
  • Language:
    English
  • Additional Information
    • Source:
      Publisher: Elsevier Country of Publication: Netherlands NLM ID: 0043535 Publication Model: Print Cited Medium: Print ISSN: 0008-6215 (Print) Linking ISSN: 00086215 NLM ISO Abbreviation: Carbohydr Res Subsets: MEDLINE
    • Publication Information:
      Publication: Amsterdam : Elsevier
      Original Publication: Amsterdam.
    • Subject Terms:
      Galactosides/*chemical synthesis ; Hexoses/*chemistry ; Polysaccharides/*chemical synthesis ; Trichinella spiralis/*chemistry; Animals ; Carbohydrate Conformation ; Carbohydrate Sequence ; Disaccharides/chemical synthesis ; Epitopes/chemistry ; Magnetic Resonance Spectroscopy ; Molecular Sequence Data ; Monosaccharides/chemical synthesis
    • Abstract:
      The anomeric configuration of tyvelose, 3,6-dideoxy-D-arabino-hexopyranose, in the recently discovered glycan epitopes of the parasite Trichinella spiralis has not been established. Two 2-(trimethylsilyl)ethyl disaccharide glycosides, alpha- and beta-Tyv-(1-->3)-beta-D-GalNAc (4 and 5), have been synthesized to provide model compounds that, together with the methyl 3,6-dideoxy-alpha- and beta-D-arabino-hexopyranosides (2 and 3), aid the determination of the anomeric configuration of tyvelose residues in the parasite glycan, either indirectly by immunochemical inhibition data or directly by the technique of 1H NMR spectroscopy. Methyl 3,6-dideoxy-beta-D-arabino-hexopyranoside (3) was synthesized from methyl 2,3-anhydro-4,6-O-benzylidene-beta-D-mannopyranoside (9) by a method previously used for the alpha anomer 2. Benzylation of 2 provided a route to the glycosyl donor, 2,4-di-O-benzyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride (30), that reacted with the selectively protected 2-acetamido-2-deoxy-D-galactopyranoside alcohol 18 in the presence of an insoluble silver zeolite catalyst to give the alpha- and beta-linked disaccharides 31 and 32. Glycosylation of the related 2-acetamido-2-deoxy-D-galactopyranoside alcohol 27 by 30 under similar conditions provided disaccharides 33 and 34 containing a tether. Deprotection of the saccharide and derivatization of the tether with 1,2-diaminoethane provided amide derivatives 35 and 36 suitable for the preparation of neoglycoconjugate antigens. Complete 1H and 13C NMR chemical shifts of the deprotected disaccharides and monosaccharides are reported.
    • Grant Information:
      AI 14490 United States AI NIAID NIH HHS
    • Accession Number:
      0 (Disaccharides)
      0 (Epitopes)
      0 (Galactosides)
      0 (Hexoses)
      0 (Monosaccharides)
      0 (Polysaccharides)
      5658-12-8 (tyvelose)
    • Publication Date:
      Date Created: 19961224 Date Completed: 19970224 Latest Revision: 20190813
    • Publication Date:
      20231215
    • Accession Number:
      10.1016/s0008-6215(96)00229-7
    • Accession Number:
      9008846