Synthesis and NKT cell stimulating properties of fluorophore- and biotin-appended 6"-amino-6"-deoxy-galactosylceramides

Org Lett. 2002 Apr 18;4(8):1267-70. doi: 10.1021/ol025565+.

Abstract

Alpha-galactosylceramides are potent stimulators of human T cells. Stimulation occurs through binding of the glycolipids by CD1d, presentation to T cells, and formation of a CD1d-glycolipid-T cell receptor complex. To facilitate the elucidation of the structural features of glycolipids necessary for T cell stimulation, alpha-galactosylceramides have been prepared with small molecules appended at the C6 position of the sugar. The appended molecules do not significantly influence the abilities of the glycolipids to stimulate T cells. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Antigens, CD1 / chemistry
  • Biotin / chemistry*
  • Carbohydrates / chemistry
  • Galactosylceramides / chemistry*
  • Galactosylceramides / pharmacology*
  • Glycolipids / chemistry
  • Humans
  • Hybridomas
  • In Vitro Techniques
  • Indicators and Reagents
  • Killer Cells, Natural / drug effects*
  • Stimulation, Chemical

Substances

  • Antigens, CD1
  • Carbohydrates
  • Galactosylceramides
  • Glycolipids
  • Indicators and Reagents
  • Biotin