Synthetic studies on glycosphingolipids from Protostomia phyla: Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis

Takeshi Yamamura, Noriyasu Hada, Asuka Kaburaki, Kimiaki Yamano, Tadahiro Takeda

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Efficient and systematic syntheses of four neutral glycosphingolipids that have been isolated from the metacestodes of Echinococcus multilocularis have been achieved. A key step is the direct glycosylation of galactosyl donors using thioglycosides with benzoyl ceramide in the presence of N-iodosuccinimide (NIS)/TfOH, which gave the desired oligosaccharide derivatives. The fully protected glycosides 13, 20, 22 and 25 were deprotected to give four target glycosphingolipids (1-4).

Original languageEnglish
Pages (from-to)2749-2759
Number of pages11
JournalCarbohydrate Research
Volume339
Issue number17
DOIs
Publication statusPublished - 2004 Dec 6

Fingerprint

Thioglycosides
Neutral Glycosphingolipids
Echinococcus multilocularis
Glycosylation
Glycosphingolipids
Ceramides
Glycosides
Oligosaccharides
Parasites
Derivatives
N-iodosuccinimide

Keywords

  • Benzoyl ceramide
  • Chemical synthesis
  • Echinococcus multilocularis
  • Glycosphingolipids

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthetic studies on glycosphingolipids from Protostomia phyla : Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis. / Yamamura, Takeshi; Hada, Noriyasu; Kaburaki, Asuka; Yamano, Kimiaki; Takeda, Tadahiro.

In: Carbohydrate Research, Vol. 339, No. 17, 06.12.2004, p. 2749-2759.

Research output: Contribution to journalArticle

Yamamura, Takeshi ; Hada, Noriyasu ; Kaburaki, Asuka ; Yamano, Kimiaki ; Takeda, Tadahiro. / Synthetic studies on glycosphingolipids from Protostomia phyla : Total syntheses of glycosphingolipids from the parasite, Echinococcus multilocularis. In: Carbohydrate Research. 2004 ; Vol. 339, No. 17. pp. 2749-2759.
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