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

Akihiko Koizumi, Kimiaki Yamano, Takashi Tsuchiya, Frank Schweizer, Fumiyuki Kiuchi, Noriyasu Hada

Research output: Contribution to journalArticle

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)9023-9042
Number of pages20
JournalMolecules
Volume17
Issue number8
DOIs
Publication statusPublished - 2012 Aug

Fingerprint

Toxocara
larvae
carbohydrates
Structure-Activity Relationship
Oligosaccharides
serums
Larva
Carbohydrates
analogs
parasites
biotin
antigens
infectious diseases
synthesis
Serum
enzymes
Trisaccharides
Immunosorbents
Azides
probes

Keywords

  • Antigenicity
  • Glycoprotein
  • Host-parasite interaction
  • Stereocontrolled synthesis
  • Toxocara larvae

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Synthesis, antigenicity against human sera and structure-activity relationships of carbohydrate moieties from toxocara larvae and their analogues. / Koizumi, Akihiko; Yamano, Kimiaki; Tsuchiya, Takashi; Schweizer, Frank; Kiuchi, Fumiyuki; Hada, Noriyasu.

In: Molecules, Vol. 17, No. 8, 08.2012, p. 9023-9042.

Research output: Contribution to journalArticle

Koizumi, Akihiko ; Yamano, Kimiaki ; Tsuchiya, Takashi ; Schweizer, Frank ; Kiuchi, Fumiyuki ; Hada, Noriyasu. / Synthesis, antigenicity against human sera and structure-activity relationships of carbohydrate moieties from toxocara larvae and their analogues. In: Molecules. 2012 ; Vol. 17, No. 8. pp. 9023-9042.
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