Pentafluoropropionyl and trifluoroacetyl groups for temporary hydroxyl group protection in oligomannoside synthesis

Carbohydr Res. 2003 May 1;338(10):1073-81. doi: 10.1016/s0008-6215(03)00099-5.

Abstract

Pentafluoropropionyl (PFP) and trifluoroacetyl (TFA) esters were demonstrated to be useful in facile oligosaccharide synthesis. These were well compatible with glycosylation conditions and removable by treatment with pyridine-EtOH, with complete preservation of acetyl groups. Analytically pure products were obtained quantitatively, simply by evaporating the reaction mixtures. Using O-PFP and O-TFA carrying glycosyl halides, trisaccharide (Manalpha1-->2Manalpha1-->2Man) and tetrasaccharide (Glcalpha1-->3Manalpha1-->2Manalpha1-->2Man) portions of monoglucosylated high-mannose type dodecasaccharide (Glc(1)Man(9)GlcNAc(2)), a putative ligand for the ER chaperon, calnexin and calreticulin, were synthesized.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Ethanol / chemistry
  • Fluorocarbons / analysis
  • Fluorocarbons / chemical synthesis*
  • Glycosylation
  • Ligands
  • Magnetic Resonance Spectroscopy / methods
  • Molecular Conformation
  • Molecular Sequence Data
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Pyridines / chemistry
  • Trifluoroacetic Acid / analysis
  • Trifluoroacetic Acid / chemical synthesis*

Substances

  • Fluorocarbons
  • Ligands
  • Oligosaccharides
  • Pyridines
  • oligomannoside
  • Ethanol
  • perfluoropropionic acid
  • Trifluoroacetic Acid
  • pyridine