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

• Published in: Chemical & pharmaceutical bulletin Vol. 67; no. 2; pp. 143 - 154
• Main Authors: Hada, Noriyasu, Umeda, Yuna, Kumada, Hiromi, Shimazaki, Yoshinori, Yamano, Kimiaki, Schweizer, Frank, Oshima, Naohiro, Takeda, Tadahiro, Kiuchi, Fumiyuki
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.02.2019; Pharmaceutical Society of Japan; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: Ascaris suum; Biotin; biotin probe; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; glycosphingolipid; Glycosphingolipids; host–parasite interaction; Life Sciences & Biomedicine; Oligosaccharides; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; stereocontrolled synthesis; Synthesis; GLYCOSIDES; ANTIGENICITY; ASSAY; STRUCTURAL ELUCIDATION; HUMAN SERA; host-parasite interaction; glycosphingolipid; biotin probe; NEMATODE; PROTOSTOMIA PHYLA SYNTHESIS; stereocontrolled synthesis; Ascaris suum; CARBOHYDRATE MOIETIES; host–parasite interaction
• ISSN: 0009-2363; 1347-5223; 1347-5223
• DOI: 10.1248/cpb.c18-00768

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 = biotinylated probe) were synthesized by stepwise condensation (1–4) and block synthesis (5) using 5-(methoxycarbonylpentyl) 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.