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

Carbohydr Res. 2002 Nov 19;337(21-23):2037-47. doi: 10.1016/s0008-6215(02)00295-1.

Abstract

Glycosphingolipids isolated from larvae of the green-bottle fly, Lucilia caesar, have quite unique structures containing GlcNAcbeta-(1 --> 3)-Man and GalNAcbeta-(1 --> 4)-GlcNAcbeta-(1 --> 3)-Man. We have synthesized two glycosphingolipids, beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-D-Glcp-(1 --> 1)-Cer and beta-D-GalNAcp-(1 --> 4)-beta-D-GlcNAcp-(1 --> 3)-beta-D-Manp-(1 --> 4)-beta-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 beta-mannopyranosidic linkages.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ascaris suum / chemistry*
  • Fucose
  • Glycosphingolipids / chemical synthesis*
  • Invertebrates / chemistry
  • Magnetic Resonance Spectroscopy
  • Mannose
  • Monosaccharides / chemical synthesis
  • Oligosaccharides / chemical synthesis

Substances

  • Glycosphingolipids
  • Monosaccharides
  • Oligosaccharides
  • Fucose
  • Mannose