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

Molecules. 2012 Jul 30;17(8):9023-42. doi: 10.3390/molecules17089023.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antibodies, Helminth / blood*
  • Antigens, Helminth / chemistry*
  • Antigens, Helminth / immunology
  • Biotin / chemistry
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Case-Control Studies
  • Disaccharides / chemical synthesis*
  • Disaccharides / immunology
  • Enzyme-Linked Immunosorbent Assay
  • Host-Parasite Interactions
  • Humans
  • Larva / immunology
  • Larva Migrans, Visceral / blood
  • Larva Migrans, Visceral / immunology*
  • Molecular Sequence Data
  • Protein Binding
  • Structure-Activity Relationship
  • Toxocara canis / immunology*
  • Trisaccharides / chemical synthesis*
  • Trisaccharides / immunology

Substances

  • Antibodies, Helminth
  • Antigens, Helminth
  • Disaccharides
  • Trisaccharides
  • Biotin