Rapid, sensitive structure analysis of oligosaccharides

Proc Natl Acad Sci U S A. 1997 Mar 4;94(5):1629-33. doi: 10.1073/pnas.94.5.1629.

Abstract

We have developed an efficient method for the derivatization of oligosaccharides, wherein the oligosaccharide is efficiently ligated to a basic aminooxyacetyl peptide by oxime formation. The resulting glycopeptide yields much higher sensitivity in matrix-assisted laser desorption/ionization mass spectrometry than does the underivatized oligosaccharide. Digestion of the glycopeptide by a exoglycosidase array and subsequent mass spectrometric assay of the digestion products provide a sensitive and rapid way to elucidate the structure of the oligosaccharide. In addition to oligosaccharide sequencing, the ligation reaction between an oligosaccharide and an aminooxyacetyl peptide also provides a potentially very convenient and efficient way for the synthesis of glycopeptides or glycoproteins.

Publication types

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

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, High Pressure Liquid
  • Glycopeptides / chemical synthesis
  • Glycopeptides / chemistry
  • Glycopeptides / metabolism
  • Glycoside Hydrolases / metabolism
  • Molecular Sequence Data
  • Oligosaccharides / chemistry*
  • Oligosaccharides / metabolism
  • Oximes / chemical synthesis
  • Sequence Analysis
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Substrate Specificity

Substances

  • Glycopeptides
  • Oligosaccharides
  • Oximes
  • Glycoside Hydrolases