An improved synthesis of dansylated α-galactosylceramide and its use as a fluorescent probe for the monitoring of glycolipid uptake by cells

Carbohydr Res. 2011 May 15;346(7):914-26. doi: 10.1016/j.carres.2011.02.014. Epub 2011 Feb 19.


A highly efficient synthesis of the biologically important fluorescent probe dansyl α-GalCer is presented. Key in our strategy is the incorporation of the fluorescent dansyl group at an early stage in the synthesis to facilitate in the monitoring and purification of intermediates via TLC and flash column chromatography, respectively, and the use of a high yielding α-selective glycosylation reaction between the phytosphingosine lipid and a galactosyl iodide donor. The ability of dansyl α-GalCer to activate iNKT cells and to serve as a fluorescent marker for the uptake of glycolipid by dendritic cells is also presented.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Dansyl Compounds / chemical synthesis*
  • Dendritic Cells / drug effects
  • Dendritic Cells / metabolism
  • Fluorescent Dyes / chemical synthesis
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / pharmacology
  • Glycolipids / metabolism
  • Mice
  • Natural Killer T-Cells / drug effects
  • Natural Killer T-Cells / metabolism


  • Dansyl Compounds
  • Fluorescent Dyes
  • Galactosylceramides
  • Glycolipids
  • alpha-galactosylceramide