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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, 2, 1, 3, 1 and 1,*
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 glycoprotein; Toxocara larvae; host-parasite interaction; stereocontrolled synthesis; antigenicity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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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