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

研究成果: Article

25 引用 (Scopus)

抄録

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).

元の言語English
ページ(範囲)600-604
ページ数5
ジャーナルChemical and Pharmaceutical Bulletin
50
発行部数5
DOI
出版物ステータスPublished - 2002 5

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

ASJC Scopus subject areas

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

これを引用

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.

:: Chemical and Pharmaceutical Bulletin, 巻 50, 番号 5, 05.2002, p. 600-604.

研究成果: Article

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. :: Chemical and Pharmaceutical Bulletin. 2002 ; 巻 50, 番号 5. pp. 600-604.
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