Synthesis and antigenicity against human sera of a biotin-labeled oligosaccharide portion of a glycosphingolipid from the parasite Echinococcus multilocularis

Noriyasu Hada, Ayaka Kitamura, Kimiaki Yamano, Frank Schweizer, Fumiyuki Kiuchi

Research output: Contribution to journalArticle

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Abstract

Synthesis of a biotinylated analog of the carbohydrate portion of a glycosphingolipid from the parasite Echinococcus multilocularis has been achieved. We synthesized β-D-Galp-(1→6)-β-D-Galp-(1→6)-[α-L-Fucp-(1→3)]-β-D-Galp-(1→R: biotin probe) (1) and compared the antigenicity by an enzyme linked immunosorbent assay (ELISA) with biotinylated trisaccharide α-D-Galp-(1→4)-β-D-Galp-(1→3)-α-D-Galp-(1→R: biotin probe) (F), which has been shown to have significant antigenicity. Both of the oligosaccharides reacted with sera of alveolar echinococcosis (AE) patients, but showed different reactivity. Among the 60 sera of AE patients, more sera reacted with the linear sequence Galα1→4Galβ1→3GalNAcα1→R of oligosaccharide (F) than for branched compound 1. Some sera showed high specificity to one of the compound, indicating that the antibodies in the sera of AE patients differ in their specificity to recognize carbohydrate sequences of glycosphingolipids. Our results demonstrate that both of the biotinylated oligosaccharides 1 and F have good serodiagnostic potential and are complementary to detect infections caused by the parasite Echinococcus multilocularis.

Original languageEnglish
Pages (from-to)865-873
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume64
Issue number7
DOIs
Publication statusPublished - 2016

Fingerprint

Echinococcus multilocularis
Glycosphingolipids
Biotin
Oligosaccharides
Parasites
Serum
Carbohydrates
Trisaccharides
Immunosorbents
Carbohydrate Sequence
Assays
Parasitic Diseases
Antibodies
Enzymes
Enzyme-Linked Immunosorbent Assay
Alveolar echinococcosis

Keywords

  • Biotin probe
  • Chemical synthesis
  • Echinococcus multilocularis
  • Glycosphingolipid

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Synthesis and antigenicity against human sera of a biotin-labeled oligosaccharide portion of a glycosphingolipid from the parasite Echinococcus multilocularis. / Hada, Noriyasu; Kitamura, Ayaka; Yamano, Kimiaki; Schweizer, Frank; Kiuchi, Fumiyuki.

In: Chemical and Pharmaceutical Bulletin, Vol. 64, No. 7, 2016, p. 865-873.

Research output: Contribution to journalArticle

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AB - Synthesis of a biotinylated analog of the carbohydrate portion of a glycosphingolipid from the parasite Echinococcus multilocularis has been achieved. We synthesized β-D-Galp-(1→6)-β-D-Galp-(1→6)-[α-L-Fucp-(1→3)]-β-D-Galp-(1→R: biotin probe) (1) and compared the antigenicity by an enzyme linked immunosorbent assay (ELISA) with biotinylated trisaccharide α-D-Galp-(1→4)-β-D-Galp-(1→3)-α-D-Galp-(1→R: biotin probe) (F), which has been shown to have significant antigenicity. Both of the oligosaccharides reacted with sera of alveolar echinococcosis (AE) patients, but showed different reactivity. Among the 60 sera of AE patients, more sera reacted with the linear sequence Galα1→4Galβ1→3GalNAcα1→R of oligosaccharide (F) than for branched compound 1. Some sera showed high specificity to one of the compound, indicating that the antibodies in the sera of AE patients differ in their specificity to recognize carbohydrate sequences of glycosphingolipids. Our results demonstrate that both of the biotinylated oligosaccharides 1 and F have good serodiagnostic potential and are complementary to detect infections caused by the parasite Echinococcus multilocularis.

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