Syntheses of model compounds related to an antigenic epitope in pectic polysaccharides from Bupleurum falcatum L.

Noriyasu Hada, Tomoko Ogino, Haruki Yamada, Tadahiro Takeda

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Abstract

Stereocontrolled syntheses of model compounds related to a category of the major antigenic epitope against anti-bupleurum 2IIc/PG-1-IgG from an anti-ulcer pectic polysaccharide are described. Glycosylation of the glucuronic acid donors methyl(2,3-di-O-benzoyl-4-O-methyl-α-D-glucopyranosyl trichloroacetimidate)uronate and methyl (2,3-di-O-benzoyl-4-O-methyl-β-D-glucopyranosyl)uronate-(1 → 6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl trichloroacetimidate with the common acceptor 2-(trimethylsilyl)ethyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside in the presence of trimethylsilyl triflate (TMSOTf) gave the desired di- and trisaccharide derivatives. Furthermore the products were transformed into the oligo-valent clustering saccharides, N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide and N,N′,N″-tri-{5-[4-O-methyl-β-D-glucopyranosyluronic acid (1 → 6)-β-D-galactopyranosyl-(1 → 6)-β-D-galactopyranosyloxy]pentylcarbonylaminoethyl}-1,3,5- benzenetriamide.

Original languageEnglish
Pages (from-to)7-17
Number of pages11
JournalCarbohydrate Research
Volume334
Issue number1
DOIs
Publication statusPublished - 2001 Aug 3

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Keywords

  • Anti-ulcer pectic polysaccharide
  • Antigenic epitope
  • Bupleurum falcatum
  • Chemical synthesis
  • Oligovalent di- and trisaccharides

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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