A synthetic divalent cholera toxin glycocalix[4]arene ligand having higher affinity than natural GM1 oligosaccharide

J Am Chem Soc. 2005 Mar 23;127(11):3660-1. doi: 10.1021/ja0444029.

Abstract

A high-affinity ligand of cholera toxin, the divalent glycocalix[4]arene 1, was obtained by exploiting a combination of structure-based design of glycomimetic monovalent ligands and affinity enhancements by multivalent presentation through a calix[4]arene scaffold. It exhibits a slightly higher affinity for the toxin than its natural ligand, the GM1 oligosaccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Calixarenes / chemistry*
  • Calixarenes / metabolism
  • Carbohydrate Sequence
  • Cholera Toxin / chemistry*
  • Cholera Toxin / metabolism
  • Glycocalyx / chemistry*
  • Glycocalyx / metabolism
  • Kinetics
  • Ligands
  • Molecular Sequence Data
  • Oligosaccharides / chemistry*
  • Oligosaccharides / metabolism
  • Phenols / chemistry*
  • Phenols / metabolism

Substances

  • Ligands
  • Oligosaccharides
  • Phenols
  • calix(4)arene
  • Calixarenes
  • G(M1)-oligosaccharide
  • Cholera Toxin