Mimetics of the tri- and tetrasaccharide epitope of GQ1balpha as myelin-associated glycoprotein (MAG) ligands

Bioorg Med Chem. 2007 Dec 1;15(23):7459-69. doi: 10.1016/j.bmc.2007.07.033. Epub 2007 Aug 21.

Abstract

The synthesis of phenoxyphenyl, phenoxybenzyl, biphenyl, and phenyltriazole substituted sialic acid derivatives as mimics of the tri- and tetrasaccharide epitopes of GQ1balpha is described. These synthetically easily available sialosides show comparable or even enhanced affinity to MAG compared with the natural tri- and tetrasaccharide epitopes and form a new class of potential MAG antagonists.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Epitopes / chemistry
  • Epitopes / pharmacology*
  • Gangliosides / chemical synthesis
  • Gangliosides / chemistry
  • Gangliosides / pharmacology*
  • Ligands
  • Models, Molecular
  • Molecular Conformation
  • Molecular Mimicry
  • Molecular Sequence Data
  • Myelin-Associated Glycoprotein / chemistry
  • Myelin-Associated Glycoprotein / drug effects*
  • N-Acetylneuraminic Acid / chemical synthesis
  • N-Acetylneuraminic Acid / chemistry
  • N-Acetylneuraminic Acid / pharmacology*
  • Polysaccharides / chemical synthesis
  • Polysaccharides / chemistry
  • Polysaccharides / pharmacology*
  • Trisaccharides / chemical synthesis
  • Trisaccharides / chemistry
  • Trisaccharides / pharmacology*

Substances

  • Epitopes
  • Gangliosides
  • Ligands
  • Myelin-Associated Glycoprotein
  • Polysaccharides
  • Trisaccharides
  • GQ1balpha ganglioside
  • N-Acetylneuraminic Acid