Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis

Noriyasu Hada, Eriko Hayashi, Tadahiro Takeda

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Novel neutral glycosphingolipids isolated from the metacestodes of Echinococcus multilocularis by Persat, may be expected to be involved in host-parasite interactions. We have synthesized these glycosphingolipid analogues containing 2-branched fatty alkyl residues in place of ceramide. The glycosylation of galactosyl donors 4 and 5 with each of the acceptors 2 and 11 in the presence of N-iodosuccinimide (NIS)/TfOH, and the glycosylation of fucosyl donor 13 with acceptors 12 and 20 in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) gave the desired oligosaccharide derivatives at good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycosides 6, 15, 21, and 26 were converted to glycosylimidates 7, 16, 22, and 27, which were condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated give four target glycosphingolipid analogues. Copyright (C) 1999 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)58-70
Number of pages13
JournalCarbohydrate Research
Volume316
Issue number1-4
DOIs
Publication statusPublished - 1999 Mar 15

Fingerprint

Echinococcus multilocularis
Glycosylation
Glycosphingolipids
Parasites
Neutral Glycosphingolipids
Host-Parasite Interactions
Ceramides
Glycosides
Oligosaccharides
Derivatives
N-iodosuccinimide
dimethyl(methylthio)sulfonium

Keywords

  • Chemical synthesis
  • Echinococcus mululocularis
  • Glycosphingolipids

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis. / Hada, Noriyasu; Hayashi, Eriko; Takeda, Tadahiro.

In: Carbohydrate Research, Vol. 316, No. 1-4, 15.03.1999, p. 58-70.

Research output: Contribution to journalArticle

Hada, Noriyasu ; Hayashi, Eriko ; Takeda, Tadahiro. / Synthetic studies on glycosphingolipids from the parasite Echinococcus multilocularis. In: Carbohydrate Research. 1999 ; Vol. 316, No. 1-4. pp. 58-70.
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