Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of a glycosphingolipid analogue from the parasite Spirometra erinacei

N. Hada, M. Kuroda, T. Takeda

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Novel neutral glycosphingolipids isolated from the plerocercoids of a tapeworm, Spirometra erinacei, may be expected to be involved in host-parasite interactions. We have synthesized this glycosphingolipid analogue containing 2-branched fatty alkyl residue in place of ceramide. Glycosylation of nonreducingo-end trisaccharide derivative 15 with the reducing-end disaccharide derivative 17 in the presence of trimethylsilyl triflate (TMSOTf) gave the desired oligosaccharide derivative in good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycoside 19 was converted to glycosylimidate 20, which was condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated to give the target glycosphingolipid analogue 22.

Original languageEnglish
Pages (from-to)1160-1165
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number8
Publication statusPublished - 2000

Fingerprint

Spirometra
Glycosphingolipids
Parasites
Neutral Glycosphingolipids
Derivatives
Trisaccharides
Host-Parasite Interactions
Cestoda
Disaccharides
Ceramides
Glycosides
Oligosaccharides
Glycosylation

Keywords

  • Chemical synthesis
  • Glycosphingolipid
  • Glycosylation
  • Spirometra erinacei

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

Cite this

Synthetic studies on glycosphingolipids from protostomia phyla : Synthesis of a glycosphingolipid analogue from the parasite Spirometra erinacei. / Hada, N.; Kuroda, M.; Takeda, T.

In: Chemical and Pharmaceutical Bulletin, Vol. 48, No. 8, 2000, p. 1160-1165.

Research output: Contribution to journalArticle

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