Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor

Bioorg Chem. 2011 Apr;39(2):88-93. doi: 10.1016/j.bioorg.2010.12.002. Epub 2010 Dec 17.

Abstract

The biological role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure-function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources; obtaining homogeneous and well-defined GPI structures by synthesis, is both a challenge and an attractive goal. We report here the convergent synthesis of the essential core of the human GPI anchor 1, exploiting a common precursor to obtain the trisaccharidic donor 2 and a novel protecting groups sequence. The final product, prepared for the first time, is biologically active.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glycosylphosphatidylinositols / chemical synthesis
  • Glycosylphosphatidylinositols / chemistry*
  • Humans
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Palladium / chemistry
  • Solvents / chemistry
  • Trisaccharides / chemistry

Substances

  • (6-O-aminoethylphosphonato-mannopyranosyl)-(1-2)-mannopyranosyl-(1-6)-mannopyranosyl-(1-4)-(2-amino-2-deoxyglucopyranosyl)-(1-6)-1-O-(1,2-di-O-octadecanoyl-sn-glyceryl-phosphonato)-myo-inositol
  • Glycosylphosphatidylinositols
  • Oligosaccharides
  • Solvents
  • Trisaccharides
  • Palladium