Synthetic studies on glycosphingolipids from protostomia phyla

Synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum

Isao Ohtsuka, Noriyasu Hada, Hiroko Ohtaka, Mutsumi Sugita, Tadahiro Takeda

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

A novel amphoteric glycosphingolipid, cholinephosphoryl-(→6)-β-D- GlcpNAc-(1→3)-β-D-Manp-(1→4)-β-D-Glcp-(1→)-Cer, isolated from the porcine parasitic nematode, Ascaris suum, may be expected to be involved in host-parasite interactions. This glycosphingolipid analogue containing octyl residue in place of ceramide was synthesized as follows: The key reaction of this synthetic procedure is the formation of a intramolecular aglycon delivery (IAD) approach for β-selective mannosylation. Then, a coupling of phosphocholine group at the position C-6″ of 16 was attempted using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by reaction of the resulting cyclic phosphate intermediate with anhydrous trimethylamine to give 17. Subsequent debenzylation and debenzylidenation afforded target compound (2).

Original languageEnglish
Pages (from-to)600-604
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume50
Issue number5
DOIs
Publication statusPublished - 2002 May

Fingerprint

Ascaris suum
Glycosphingolipids
Glycolipids
Swine
Host-Parasite Interactions
Phosphorylcholine
Ceramides
Phosphates
trimethylamine
Parasites

Keywords

  • β-mannosidic linkage
  • Amphoteric glycosphingolipid
  • Ascaris suum
  • Chemical synthesis
  • Phosphocholine

ASJC Scopus subject areas

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

Cite this

Synthetic studies on glycosphingolipids from protostomia phyla : Synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum. / Ohtsuka, Isao; Hada, Noriyasu; Ohtaka, Hiroko; Sugita, Mutsumi; Takeda, Tadahiro.

In: Chemical and Pharmaceutical Bulletin, Vol. 50, No. 5, 05.2002, p. 600-604.

Research output: Contribution to journalArticle

Ohtsuka, Isao ; Hada, Noriyasu ; Ohtaka, Hiroko ; Sugita, Mutsumi ; Takeda, Tadahiro. / Synthetic studies on glycosphingolipids from protostomia phyla : Synthesis of amphoteric glycolipid analogues from the porcine nematode, Ascaris suum. In: Chemical and Pharmaceutical Bulletin. 2002 ; Vol. 50, No. 5. pp. 600-604.
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