Divergent synthetic approach to 6''-modified α-GalCer analogues

Org Biomol Chem. 2011 Dec 21;9(24):8413-21. doi: 10.1039/c1ob06235b. Epub 2011 Nov 1.

Abstract

A synthetic approach is presented for the synthesis of galacturonic acid and D-fucosyl modified KRN7000. The approach allows for late-stage functionalisation of both the sugar 6''-OH and the sphingosine amino groups, which enables convenient synthesis of promising 6''-modified KRN7000 analogues.

Publication types

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

MeSH terms

  • Animals
  • Cytokines / metabolism
  • Galactosylceramides / administration & dosage
  • Galactosylceramides / chemical synthesis*
  • Galactosylceramides / chemistry
  • Hexuronic Acids / administration & dosage
  • Hexuronic Acids / chemical synthesis*
  • Hexuronic Acids / chemistry
  • Mice
  • Molecular Conformation
  • Stereoisomerism
  • Surface Plasmon Resonance

Substances

  • Cytokines
  • Galactosylceramides
  • Hexuronic Acids
  • galacturonic acid
  • KRN 7000