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 journalArticle

Abstract

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
Volume67
Issue number2
DOIs
Publication statusPublished - 2019 Jan 1

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Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Hada, N., Umeda, Y., Kumada, H., Shimazaki, Y., Yamano, K., Schweizer, F., Oshima, N., Takeda, T., & Kiuchi, F. (2019). Synthesis of the Non Reducing End Oligosaccharides of Glycosphingolipids from Ascaris suum. Chemical and Pharmaceutical Bulletin, 67(2), 143-154. https://doi.org/10.1248/cpb.c18-00768