The total synthesis of a ganglioside Hp-s1 analogue possessing neuritogenic activity by chemoselective activation glycosylation

Org Biomol Chem. 2012 Feb 7;10(5):931-4. doi: 10.1039/c2ob06827c. Epub 2011 Dec 19.

Abstract

The total synthesis of ganglioside 2, an analogue of the ganglioside Hp-s1 (1) which displays neuritogenic activity toward the rat pheochromocytoma cell line PC-12 cell in the presence of nerve growth factor (NGF) with an effect (34.0%) greater than that of the mammalian ganglioside GM 1 (25.4%), was accomplished by applying a chemoselective-activation glycosylation strategy. Moreover, we also demonstrate that the synthesized ganglioside 2 exhibited neuritogenic activity toward the human neuroblastoma cell line SH-SY5Y without the presence of NGF.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Line, Tumor
  • G(M1) Ganglioside / pharmacology
  • Gangliosides / chemical synthesis
  • Gangliosides / chemistry*
  • Gangliosides / pharmacology*
  • Glycosylation
  • Humans
  • Nerve Growth Factor / pharmacology
  • Neurites / drug effects*
  • Neurites / physiology
  • PC12 Cells
  • Rats

Substances

  • Gangliosides
  • G(M1) Ganglioside
  • Nerve Growth Factor