Synthesis and galectin-binding activities of mercaptododecyl glycosides containing a terminal β-galactosyl group

Bioorg Med Chem Lett. 2011 Feb 15;21(4):1265-9. doi: 10.1016/j.bmcl.2010.12.049. Epub 2010 Dec 16.

Abstract

Mercaptododecyl glycosides containing a terminal β-galactosyl group were prepared from D-galactose or from D-lactose via hexa-O-acetyl-lactal (10) as a key intermediate. Interactions of these glycolipids (5 kinds) and galectins (β-galactoside binding lectins, 6 species) were evaluated by surface plasmon resonance (SPR) method. High binding responses were observed for the lactoside, 2-deoxy-lactoside, and lactosaminide with some galectins (Gal-3, -4, -8), whereas the galactoside and 2,3-dideoxy-lactoside showed low binding activities.

MeSH terms

  • Galactose / chemistry*
  • Galectins / chemistry*
  • Glycosides / chemical synthesis
  • Glycosides / chemistry*
  • Kinetics
  • Protein Binding
  • Sulfhydryl Compounds / chemistry*
  • Surface Plasmon Resonance

Substances

  • Galectins
  • Glycosides
  • Sulfhydryl Compounds
  • Galactose