Chemical Synthesis of Gangliosides

Methods Mol Biol. 2018:1804:293-310. doi: 10.1007/978-1-4939-8552-4_14.

Abstract

Various methods for the chemical synthesis of gangliosides have been investigated to date and numerous natural gangliosides and their structural analogues have been synthesized during the past three decades. Key technologies in the synthesis of gangliosides include α-selective sialylation and introduction of the ceramide moiety into the oligosaccharide chain. This chapter introduces two major strategies for ganglioside synthesis-the most commonly used strategy and the recently developed glucosylceramide cassette approach. Synthetic procedures for selected reactions are also presented.

Keywords: Ganglioside; Glycolipid; Glycosylation; Sialylation; Total synthesis.

MeSH terms

  • Animals
  • Chemistry, Organic / methods*
  • Galactose / metabolism
  • Gangliosides / chemical synthesis*
  • Gangliosides / chemistry
  • Glucosylceramides / metabolism
  • Mammals
  • Molecular Conformation
  • N-Acetylneuraminic Acid / metabolism

Substances

  • Gangliosides
  • Glucosylceramides
  • N-Acetylneuraminic Acid
  • Galactose