title: 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 Galβ1-3GalNAc core of the TES-glycoprotein antigen obtained from larvae of the parasite Toxocara and their analogues have been accomplished. Trisaccharides Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2Galβ1-3GalNAcα1-OR (D) and a disaccharide Fuc2Meα1-2Gal4Meβ1-OR (E) (R = biotinylated probe) were synthesized by block synthesis using 5-(methoxycarbonyl)pentyl-2,3,4,6-tetra-O-acetyl-β-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.
authors: Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan.
authors: Akihiko
authors: A
authors: Koizumi
authors: Kimiaki
authors: K
authors: Yamano
authors: Takashi
authors: T
authors: Tsuchiya
authors: Frank
authors: F
authors: Schweizer
authors: Fumiyuki
authors: F
authors: Kiuchi
authors: Noriyasu
authors: N
authors: Hada
mesh_terms: D000818:Animals; D000909:Antibodies, Helminth / Q000097:blood*; D000947:Antigens, Helminth / Q000737:chemistry* / Q000276:immunology; D001710:Biotin / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D016022:Case-Control Studies; D004187:Disaccharides / Q000138:chemical synthesis* / Q000276:immunology; D004797:Enzyme-Linked Immunosorbent Assay; D006790:Host-Parasite Interactions; D006801:Humans; D007814:Larva / Q000276:immunology; D007816:Larva Migrans, Visceral / Q000097:blood / Q000276:immunology*; D008969:Molecular Sequence Data; D011485:Protein Binding; D013329:Structure-Activity Relationship; D017166:Toxocara canis / Q000276:immunology*; D014312:Trisaccharides / Q000138:chemical synthesis* / Q000276:immunology
chemical_list: D000909:Antibodies, Helminth; D000947:Antigens, Helminth; D004187:Disaccharides; D014312:Trisaccharides; D001710:Biotin