Synthesis and biological activity of alpha-galactosyl ceramide KRN7000 and galactosyl (alpha1-->2) galactosyl ceramide

Bioorg Med Chem Lett. 2009 Aug 1;19(15):4288-91. doi: 10.1016/j.bmcl.2009.05.095. Epub 2009 May 27.

Abstract

We herein report a faster and less cumbersome synthesis of the biologically attractive, alpha-galactosyl ceramide (alpha-GalCer), known as KRN7000, and its analogues. More importantly, the use of a silicon tethered intramolecular glycosylation reaction gave easy access to the diglycosyl ceramide Gal(alpha1-->2)GalCer, which has been shown to require uptake and processing to the biologically active alpha-GalCer derivative.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antigens, CD1d / chemistry
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Galactosylceramides / pharmacology
  • Glycosides / chemistry
  • Humans
  • Killer Cells, Natural / cytology
  • Mice
  • Models, Chemical
  • Th2 Cells / metabolism

Substances

  • Antigens, CD1d
  • Antineoplastic Agents
  • Galactosylceramides
  • Glycosides
  • alpha-galactosylceramide
  • KRN 7000