Synthesis of all stereoisomers of KRN7000, the CD1d-binding NKT cell ligand

Bioorg Med Chem Lett. 2008 Jul 15;18(14):3906-9. doi: 10.1016/j.bmcl.2008.06.036. Epub 2008 Jun 14.

Abstract

KRN7000 is an important ligand identified for CD1d protein of APC, and KRN7000/CD1d complex can stimulate NKT cells to release Th1 and Th2 cytokines. In an effort to understand the structure-activity relationships, we have carried out the synthesis of a complete set of the eight KRN7000 stereoisomers, and their biological activities have been examined.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adjuvants, Immunologic / chemical synthesis
  • Adjuvants, Immunologic / chemistry
  • Antigens, CD1 / chemistry*
  • Antigens, CD1 / metabolism
  • Antigens, CD1d
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry*
  • Humans
  • Killer Cells, Natural / immunology*
  • Killer Cells, Natural / metabolism
  • Ligands
  • Models, Chemical
  • Protein Binding
  • Stereoisomerism

Substances

  • Adjuvants, Immunologic
  • Antigens, CD1
  • Antigens, CD1d
  • CD1D protein, human
  • Galactosylceramides
  • Ligands
  • alpha-galactosylceramide
  • KRN 7000