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Chem Pharm Bull (Tokyo) ; 67(2): 143-154, 2019.
Article in English | MEDLINE | ID: mdl-30713275

ABSTRACT

Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the non reducing end oligosaccharides of glycosphingolipids from Ascaris suum have been accomplished. Galα1→3GalNAcß1→OR (1), Galß1→3Galα1→3GalNAcß1→OR (2), Galß1→6Galα1→3GalNAcß1→OR (3), Galß1→6(Galß1→3)Galα1→3GalNAcß1→OR (4) and GlcNAcß1→6Galß1→6(Galß1→3)Galα1→3GalNAcß1→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-ß-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.


Subject(s)
Ascaris suum/chemistry , Glycosphingolipids/chemical synthesis , Oligosaccharides/chemical synthesis , Animals , Biotin/chemistry , Glycosphingolipids/chemistry , Magnetic Resonance Spectroscopy , Oligosaccharides/chemistry , Oxidation-Reduction
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