Synthetic studies on glycosphingolipids from the Protostomia phyla: Syntheses of arthro-series glycosphingolipids

Isao Ohtsuka, Noriyasu Hada, Mutsumi Sugita, Tadahiro Takeda

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcβ-(1→3)-Man and GalNAcβ-(1→4)-GlcNAcβ-(1→3)-Man. We have synthesized two glycosphingolipids, β-D-GlcNAcp-(1→3)-β-D-Manp-(1→4)-β-D-Glcp- (1→1)-Cer and β-D-GalNAcp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-Manp- (1→4)-β-D-Glcp-(1→1)-Cer. A key reaction in the synthetic sequence is the application of the intramolecular aglycon delivery (IAD) approach for the synthesis of the β-mannopyranosidic linkages.

Original languageEnglish
Pages (from-to)2037-2047
Number of pages11
JournalCarbohydrate Research
Volume337
Issue number21-23
DOIs
Publication statusPublished - 2002 Nov 19

Keywords

  • Arthro-series
  • Chemical synthesis
  • Glycosphingolipids
  • Lucilia caesar

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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