Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

Akihiko Koizumi, Kimiaki Yamano, Frank Schweizer, Tadahiro Takeda, Fumiyuki Kiuchi, Noriyasu Hada

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Galβ1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (G), tetrasaccharide Galβ1-3(Galβ1-4GlcNAcβ1-6)GalNAcα1-R (J) and pentasaccharide Galβ1-3(Galα1-4Galβ1-4GlcNAcβ1-6) GalNAcα1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-β- d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d- galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Galα1-4Galβ1-3GalNAcα1-R (H) and branched tetrasaccharide Galα1-4Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (I) were synthesized by stepwise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Galα1-4Galβ1- 3GalNAcα1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen.

Original languageEnglish
Pages (from-to)1768-1778
Number of pages11
JournalEuropean Journal of Medicinal Chemistry
Volume46
Issue number5
DOIs
Publication statusPublished - 2011 May

Fingerprint

Echinococcus multilocularis
Oligosaccharides
Parasites
Carbohydrates
Trisaccharides
Serum
Antigens
Immunosorbents
Parasitic Diseases
Biotin
Galactose
Epitopes
Condensation
Assays
Glycoproteins
Enzyme-Linked Immunosorbent Assay
Enzymes

Keywords

  • Antigenicity
  • Echinococcus multilocularis
  • Glycoprotein
  • Host-parasite interactions
  • Stereocontrolled synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera. / Koizumi, Akihiko; Yamano, Kimiaki; Schweizer, Frank; Takeda, Tadahiro; Kiuchi, Fumiyuki; Hada, Noriyasu.

In: European Journal of Medicinal Chemistry, Vol. 46, No. 5, 05.2011, p. 1768-1778.

Research output: Contribution to journalArticle

Koizumi, Akihiko ; Yamano, Kimiaki ; Schweizer, Frank ; Takeda, Tadahiro ; Kiuchi, Fumiyuki ; Hada, Noriyasu. / Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera. In: European Journal of Medicinal Chemistry. 2011 ; Vol. 46, No. 5. pp. 1768-1778.
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abstract = "Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Galβ1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (G), tetrasaccharide Galβ1-3(Galβ1-4GlcNAcβ1-6)GalNAcα1-R (J) and pentasaccharide Galβ1-3(Galα1-4Galβ1-4GlcNAcβ1-6) GalNAcα1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-β- d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d- galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Galα1-4Galβ1-3GalNAcα1-R (H) and branched tetrasaccharide Galα1-4Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (I) were synthesized by stepwise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Galα1-4Galβ1- 3GalNAcα1-R in oligosaccharide (H) appears to show the highest sensitivity (95{\%}). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen.",
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AU - Koizumi, Akihiko

AU - Yamano, Kimiaki

AU - Schweizer, Frank

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AU - Kiuchi, Fumiyuki

AU - Hada, Noriyasu

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AB - Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Galβ1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (G), tetrasaccharide Galβ1-3(Galβ1-4GlcNAcβ1-6)GalNAcα1-R (J) and pentasaccharide Galβ1-3(Galα1-4Galβ1-4GlcNAcβ1-6) GalNAcα1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-β- d-galactopyranosyl-(1→3)-2-azido-4-O-benzyl-2-deoxy-α-d- galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Galα1-4Galβ1-3GalNAcα1-R (H) and branched tetrasaccharide Galα1-4Galβ1-3(GlcNAcβ1-6)GalNAcα1-R (I) were synthesized by stepwise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Galα1-4Galβ1- 3GalNAcα1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen.

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