Molecules 2012, 17(8), 9023-9042; doi:10.3390/molecules17089023
Article

Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues

1 Faculty of Pharmacy, Keio University, 1-5-30 Shibakoen, Minato-ku, Tokyo 105-8512, Japan 2 Hokkaido Institute of Public Health, Kita-19, Nishi-12, Kita-ku, Sapporo 060-0819, Japan 3 Departments of Chemistry and Medical Microbiology, University of Manitoba, Winnipeg, MB R3T 2N2, Canada
* Author to whom correspondence should be addressed.
Received: 21 June 2012; in revised form: 20 July 2012 / Accepted: 23 July 2012 / Published: 30 July 2012
(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)
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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.
Keywords: glycoprotein; Toxocara larvae; host-parasite interaction; stereocontrolled synthesis; antigenicity

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MDPI and ACS Style

Koizumi, A.; Yamano, K.; Tsuchiya, T.; Schweizer, F.; Kiuchi, F.; Hada, N. Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues. Molecules 2012, 17, 9023-9042.

AMA Style

Koizumi A, Yamano K, Tsuchiya T, Schweizer F, Kiuchi F, Hada N. Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues. Molecules. 2012; 17(8):9023-9042.

Chicago/Turabian Style

Koizumi, Akihiko; Yamano, Kimiaki; Tsuchiya, Takashi; Schweizer, Frank; Kiuchi, Fumiyuki; Hada, Noriyasu. 2012. "Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues." Molecules 17, no. 8: 9023-9042.

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