%0 Journal Article
%T Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues
%A Akihiko Koizumi
%A Kimiaki Yamano
%A Takashi Tsuchiya
%A Frank Schweizer
%A Fumiyuki Kiuchi
%A Noriyasu Hada
%J Molecules
%D 2012
%I MDPI AG
%R 10.3390/molecules17089023
%X Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the Gal¦Â1-3GalNAc core of the TES-glycoprotein antigen obtained from larvae of the parasite Toxocara and their analogues have been accomplished. Trisaccharides Fuc2Me¦Á1-2Gal4Me¦Â1-3GalNAc¦Á1-OR (A), Fuc¦Á1-2Gal4Me¦Â1-3GalNAc¦Á1-OR (B), Fuc2Me¦Á1-2Gal¦Â1-3GalNAc¦Á1-OR (C), Fuc¦Á1-2Gal¦Â1-3GalNAc¦Á1-OR (D) and a disaccharide Fuc2Me¦Á1-2Gal4Me¦Â1-OR (E) (R = biotinylated probe) were synthesized by block synthesis using 5-(methoxycarbonyl)pentyl-2,3,4,6-tetra-O-acetyl-¦Â-D-galactopyranosyl-(1£¿3)-2-azide-4-O-benzyl-2-deoxy-¦Á-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.
%K glycoprotein
%K Toxocara larvae
%K host-parasite interaction
%K stereocontrolled synthesis
%K antigenicity
%U http://www.mdpi.com/1420-3049/17/8/9023