Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum

Noriyasu Hada, Yuna Umeda, Hiromi Kumada, Yoshinori Shimazaki, Kimiaki Yamano, Frank Schweizer, Naohiro Oshima, Tadahiro Takeda, Fumiyuki Kiuchi

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcβ1→OR (1), Galβ1→3Galα1→3GalNAcβ1→OR (2), Galβ1→6Galα1→3GalNAcβ1→OR (3), Galβ1→6(Galβ1→3) Galα1→3GalNAcβ1→OR (4) and GlcNAcβ1→6Galβ1→6(Galβ1→3)Galα1→3GalNAcβ1→OR (5) (R=bioti-nylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycar-bonylpentyl) 2-O-benzoyl-3-O-2-napthylmethyl-4,6-O-di-tert-butylsilylene-α-D-galactopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-galactopyranoside (12) as a common precursor. Compound 12 was converted into two kinds of glycosyl acceptors and was condensed with suitable galactosyl donors, respectively.

Original languageEnglish
Pages (from-to)143-154
Number of pages12
JournalChemical and Pharmaceutical Bulletin
Issue number2
Publication statusPublished - 2019


  • Ascaris suum
  • Biotin probe
  • Glycosphingolipid
  • Host–parasite interaction
  • Stereocontrolled synthesis

ASJC Scopus subject areas

  • General Chemistry
  • Drug Discovery


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