A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo-GM1b

Carbohydr Res. 2002 Oct 8;337(18):1679-86. doi: 10.1016/s0008-6215(02)00259-8.

Abstract

A first total synthesis of a novel sulfated ganglioside, 3'-O-sulfo-GM1b, is described. The suitably protected gangliotriose (GgOSe3) derivative, 2-(trimethylsilyl)ethyl (2-acetamido-4,6-O-benzylidene-2-deoxy-beta-D-galactopyranosyl)-(1-->4)-(2,6-di-O-benzyl-3-O-p-methoxybenzyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O-benzyl-beta-D-glucopyranoside was glycosylated with the alpha-NeuAc-(2-->3)-galactose donor to give the protected GM1b oligosaccharide (95%). After proper manipulation of the protecting groups, the oligosaccharide was converted into the target ganglioside by the successive introduction of the ceramide and sulfo groups, followed by complete deprotection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Ceramides / chemistry
  • G(M1) Ganglioside / analogs & derivatives
  • G(M1) Ganglioside / chemical synthesis*
  • Gangliosides / chemical synthesis*
  • Glycosylation
  • Magnetic Resonance Spectroscopy
  • Molecular Sequence Data
  • Spectrometry, Mass, Fast Atom Bombardment
  • Sulfates / chemical synthesis*
  • Sulfates / chemistry*

Substances

  • 3'-O-sulfo-ganglioside M1b
  • Ceramides
  • Gangliosides
  • Sulfates
  • G(M1) Ganglioside