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 language | English |
|---|---|
| Pages (from-to) | 9023-9042 |
| Number of pages | 20 |
| Journal | Molecules |
| Volume | 17 |
| Issue number | 8 |
| DOIs | |
| Publication status | Published - 2012 Aug |
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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 journal › Article
}
TY - JOUR
T1 - Synthesis, antigenicity against human sera and structure-activity relationships of carbohydrate moieties from toxocara larvae and their analogues
AU - Koizumi, Akihiko
AU - Yamano, Kimiaki
AU - Tsuchiya, Takashi
AU - Schweizer, Frank
AU - Kiuchi, Fumiyuki
AU - Hada, Noriyasu
PY - 2012/8
Y1 - 2012/8
N2 - 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.
AB - 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.
KW - Antigenicity
KW - Glycoprotein
KW - Host-parasite interaction
KW - Stereocontrolled synthesis
KW - Toxocara larvae
UR - http://www.scopus.com/inward/record.url?scp=84865490891&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84865490891&partnerID=8YFLogxK
U2 - 10.3390/molecules17089023
DO - 10.3390/molecules17089023
M3 - Article
C2 - 22847142
AN - SCOPUS:84865490891
VL - 17
SP - 9023
EP - 9042
JO - Molecules
JF - Molecules
SN - 1420-3049
IS - 8
ER -