A novel Gal(beta1-4)Gal(beta1-4)Fuc(alpha1-6)-core modification attached to the proximal N-acetylglucosamine of keyhole limpet haemocyanin (KLH) N-glycans

Biochem J. 2004 Mar 1;378(Pt 2):625-32. doi: 10.1042/BJ20031380.

Abstract

KLH (keyhole limpet haemocyanin), the oxygen-carrying molecule of the marine snail Megathura crenulata, is often used as an adjuvant or as a hapten carrier for immunizations with peptides, oligosaccharides or other low-molecular-mass organic compounds. KLH exhibits several carbohydrate determinants, at least some of which are immunogenic: it shares an antigenic Fuc(alpha1-3)GalNAc-determinant with schistosomes and contains unique Gal-(beta1-6)Man-structural motifs on its N-glycans. This study reveals the presence of N-glycans with unusual +/-Gal(beta1-4)Gal(beta1-4)Fuc- units (alpha1-6)-linked to the reducing end N -acetylglucosamine residue. The following novel structures of KLH N-glycans were deduced by linkage analysis, exoglycosidase digestion, matrix-assisted laser-desorption ionization-tandem MS and nano-LC-ESI-IT-MS (where LC stands for liquid chromatography, ESI for electrospray ionization and IT for ion trap): Man(alpha1-6)[+/-Man(alpha1-3)]Man(beta1-4)GlcNAc(beta1-4)[Gal(beta1-4)Fuc(alpha1-6)]GlcNAc and Man(alpha1-6)Man(beta1-4)GlcNAc(beta1-4)[Gal(beta1-4)Gal(beta1-4)Fuc(alpha1-6)]GlcNAc. The Gal(beta1-4)Fuc- and Gal(beta1-4)Gal(beta1-4)Fuc- core modifications are expected to be immunogenic, similar to other non-mammalian-type core modifications, and to contribute to the immunostimulatory properties of KLH.

MeSH terms

  • Acetylglucosamine / analysis*
  • Carbohydrate Sequence
  • Carbohydrates / analysis
  • Fucose / analysis*
  • Galactose / analysis*
  • Hemocyanins / chemistry*
  • Molecular Sequence Data
  • Polysaccharides / analysis
  • Polysaccharides / chemistry*
  • Polysaccharides / isolation & purification
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization

Substances

  • Carbohydrates
  • Polysaccharides
  • Fucose
  • Hemocyanins
  • keyhole-limpet hemocyanin
  • Acetylglucosamine
  • Galactose