Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of amphoteric glycolipid analogues containing a phosphocholine residue from the earthworm Pheretima hilgendorfi

N. Hada, K. Sato, J. I. Sakushima, Y. Goda, M. Sugita, T. Takeda

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Two kinds of amphoteric glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows: The key reaction is a coupling of a phosphocholine group at the position C-6 of 1 and 6 which 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 2 and 7. Subsequent debenzylation afforded target compounds (3, 8). Their ability to inhibit the histamine release in vitro was examined.

Original languageEnglish
Pages (from-to)1464-1467
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume49
Issue number11
DOIs
Publication statusPublished - 2001

Keywords

  • Amphoteric glycosphingolipid
  • Chemical synthesis
  • Pheretima hilgendorfi
  • Phosphocholine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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