Synthesis of a small library of bivalent α-D-mannopyranosides for lectin cross-linking

Carbohydr Res. 2011 Sep 6;346(12):1479-89. doi: 10.1016/j.carres.2011.03.041. Epub 2011 Apr 6.

Abstract

A small library of bivalent α-D-mannopyranosides having rigid linkers was constructed in order to evaluate the effects of inter-saccharide distances upon multivalent binding interactions with plant and bacterial lectins. To this end, iodoaryl and propargyl α-D-mannopyranosides were synthesized and the former treated with TMS-acetylene under palladium chemistry to provide their corresponding ethynylaryl derivatives. A library of 15 dimeric members was then obtained using Lewis acid catalyzed glycosidation, aryl-aryl homocoupling, transition metal catalyzed Sonogashira cross-coupling reactions, and oxidative Glaser homocoupling.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacteria
  • Bacterial Proteins / chemistry*
  • Bacterial Proteins / metabolism
  • Carbohydrate Conformation
  • Catalysis
  • Combinatorial Chemistry Techniques / methods*
  • Cross-Linking Reagents
  • Dimerization
  • Glycoconjugates / chemical synthesis*
  • Glycoconjugates / metabolism
  • Lewis Acids / chemistry
  • Mannose / chemical synthesis*
  • Mannose / metabolism
  • Palladium / chemistry
  • Plant Lectins / chemistry*
  • Plant Lectins / metabolism
  • Plants
  • Protein Binding
  • Receptors, Mitogen / chemistry
  • Receptors, Mitogen / metabolism
  • Small Molecule Libraries / chemical synthesis*
  • Small Molecule Libraries / metabolism

Substances

  • Bacterial Proteins
  • Cross-Linking Reagents
  • Glycoconjugates
  • Lewis Acids
  • Plant Lectins
  • Receptors, Mitogen
  • Small Molecule Libraries
  • Palladium
  • Mannose