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

研究成果: Article査読

抄録

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.

本文言語English
ページ(範囲)143-154
ページ数12
ジャーナルChemical and Pharmaceutical Bulletin
67
2
DOI
出版ステータスPublished - 2019

ASJC Scopus subject areas

  • 化学 (全般)
  • 創薬

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