The Galβ-(syn)-gauche configuration is required for galectin-recognition disaccharides

Biochim Biophys Acta. 2011 Jul;1810(7):643-51. doi: 10.1016/j.bbagen.2011.04.001. Epub 2011 Apr 15.

Abstract

Background: Galectins form a large family of animal lectins, individual members having variously divergent carbohydrate-recognition domains (CRDs) responsible for extensive physiological phenomena. Sugar-binding affinities of galectins were previously investigated by us using frontal affinity chromatography (FAC) with a relatively small set (i.e., 41) of oligosaccharides. However, total understanding of a consensus rule for galectin-recognition saccharides is still hampered by the lack of fundamental knowledge about their sugar-binding specificity toward a much larger panel of oligosaccharides in terms of dissociation constant (K(d)).

Methods: In the present study, we extended a FAC analysis from a more systematic viewpoint by using 142 fluorescent-labeled oligosaccharides, initially with focus on functional human galectins-1-9. Binding characteristics were further validated with 11 non-human galectins and 13 non-galectin Gal/GalNAc-binding lectins belonging to different families.

Results: An empirical [Galβ-equatorial] rule for galectin-recognition disaccharides was first derived by our present research and previous works by others. However, this rule was not valid for a recently reported nematode disaccharide, "Galβ1-4-L-Fuc" [Butschi et al. PLoS Pathog, 2010; 6(1):e1000717], because this glycosidic linkage was directed to 'axial' 4-OH of L-Fuc. After careful reconsideration of the structural data, we reached an ultimate rule of galectin-recognition disaccharides, which all of the galectins so far identified fulfilled, i.e., under the re-defined configuration "Galβ-(syn)-gauche". The rule also worked perfectly for differentiation of galectins from other types of lectins.

General significance: The present attempt should provide a basis to solve the riddle of the glyco-code as well as to develop therapeutic inhibitors mimicking galectin ligands.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites
  • Binding, Competitive
  • Chromatography, Affinity / instrumentation
  • Chromatography, Affinity / methods*
  • Disaccharides / chemistry*
  • Disaccharides / metabolism
  • Galectins / chemistry*
  • Galectins / genetics
  • Galectins / metabolism
  • Humans
  • Molecular Conformation*
  • Molecular Structure
  • Oligosaccharides / chemistry
  • Protein Binding
  • Protein Isoforms / chemistry
  • Protein Isoforms / genetics
  • Protein Isoforms / metabolism
  • Recombinant Proteins / chemistry
  • Recombinant Proteins / metabolism

Substances

  • Disaccharides
  • Galectins
  • Oligosaccharides
  • Protein Isoforms
  • Recombinant Proteins