Synthesis, antigenicity against human sera and structure-activity relationships of carbohydrate moieties from Toxocara larvae and their analogues.

ABSTRACT

Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the Galß1-3GalNAc core of the TES-glycoprotein antigen obtained from larvae of the parasite Toxocara and their analogues have been accomplished. Trisaccharides Fuc2Meα1-2Gal4Meß1-3GalNAcα1-OR (A), Fucα1-2Gal4Meß1-3GalNAcα1-OR (B), Fuc2Meα1-2Galß1-3GalNAcα1-OR (C), Fucα1-2Galß1-3GalNAcα1-OR (D) and a disaccharide Fuc2Meα1-2Gal4Meß1-OR (E) (R = biotinylated probe) were synthesized by block synthesis using 5-(methoxycarbonyl)pentyl-2,3,4,6-tetra-O-acetyl-ß-D-galactopyranosyl-(1-->3)-2-azide-4-O-benzyl-2-deoxy-α-D-galactopyranoside as a common glycosyl acceptor. We examined the antigenicity of these five oligosaccharides by enzyme linked immunosorbent assay (ELISA). Our results demonstrate that the O-methyl groups in these oligosaccharides are important for their antigenicity and the biotinylated oligosaccharides A, B, C and E have high serodiagnostic potential to detect infections caused by Toxocara larvae.