Investigation of different combinations of derivatization, separation methods and electrospray ionization mass spectrometry for standard oligosaccharides and glycans from ovalbumin

J Mass Spectrom. 2001 May;36(5):563-74. doi: 10.1002/jms.158.

Abstract

Derivatization procedures using 1-phenyl-3-methyl-5-pyrazolone (PMP) and 2-aminonaphthalene trisulfone (ANTS) were selected among a number of well known methods for labelling carbohydrates. PMP derivatives were selected owing to our laboratory's previous high-performance liquid chromatography/electrospray ionization mass spectrometry (HPLC/ESI-MS) experience with these, whereas the ANTS-labelled compounds were prepared for fluorophore-assisted carbohydrate electrophoresis (FACE) separation. ANTS-oligosaccharide standards were characterized to study their ionization patterns. Reversed-phase and normal-phase HPLC systems were coupled on-line with ESI-MS. Each necessitated its own mobile phase system which, in turn, imposed some important changes in the ionization conditions used and/or on the ionization patterns and spectra obtained. Following characterization of the intact glycoprotein ovalbumin with ESI-MS, its glycans were detached using the enzyme PNGase-F. The glycans were subjected to PMP and ANTS derivatization. It was very difficult to separate ANTS derivatives by reversed-phase HPLC owing to lack of retention, and normal-phase HPLC offered reasonable retention with limited separation. PMP compounds overall yielded better normal- and reversed-phase separations and improved sensitivity over the ANTS-labelled sugars, for which negative mode ESI had to be used. The combination of ESI of intact ovalbumin and ESI of PMP-glycans gave rise to the detection of over 20 different glycoforms, excluding the possible presence of structural isomers for each sugar composition detected.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidohydrolases
  • Animals
  • Antipyrine / analogs & derivatives
  • Carbohydrate Sequence
  • Chickens
  • Chromatography, High Pressure Liquid
  • Edaravone
  • Fluorescent Dyes
  • Molecular Sequence Data
  • Naphthalenes
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Ovalbumin / chemistry*
  • Peptide-N4-(N-acetyl-beta-glucosaminyl) Asparagine Amidase
  • Polysaccharides / chemistry*
  • Polysaccharides / isolation & purification
  • Spectrometry, Mass, Electrospray Ionization*

Substances

  • Fluorescent Dyes
  • Naphthalenes
  • Oligosaccharides
  • Polysaccharides
  • Ovalbumin
  • 8-amino-1,3,6-naphthalenetrisulfonic acid
  • Amidohydrolases
  • Peptide-N4-(N-acetyl-beta-glucosaminyl) Asparagine Amidase
  • Edaravone
  • Antipyrine