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

研究成果: Article査読

9 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)9023-9042
ページ数20
ジャーナルMolecules
17
8
DOI
出版ステータスPublished - 2012 8

ASJC Scopus subject areas

  • 分析化学
  • 化学(その他)
  • 分子医療
  • 薬科学
  • 創薬
  • 物理化学および理論化学
  • 有機化学

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