Efficient synthesis of galactosylceramide analogues for iNKT cell stimulation

Bioorg Med Chem Lett. 2010 Jul 1;20(13):3859-62. doi: 10.1016/j.bmcl.2010.05.045. Epub 2010 May 15.

Abstract

Glycolipids are potential antigens for iNKT cells recognition and demonstrate important roles in both innate and adaptive immunity. However, the difficulties in the preparation of pure configuration defined glycolipids limit the exploration of their different profiles in activating iNKT cells. We report here a concise and stereospecific preparation of novel galactosylceramide analogues by oxime ligation. This strategy would provide an efficient way to generate varied glycolipid analogues with either synthetic or natural carbohydrates for biological evaluations.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Galactosylceramides / pharmacology*
  • Humans
  • Molecular Structure
  • Natural Killer T-Cells / drug effects*
  • Natural Killer T-Cells / immunology
  • Porifera / chemistry
  • Stereoisomerism

Substances

  • Galactosylceramides