Click to fit: versatile polyvalent display on a peptidomimetic scaffold

Org Lett. 2005 May 12;7(10):1951-4. doi: 10.1021/ol050371q.


We describe an efficient protocol to effect multisite conjugation reactions to oligomers on solid-phase support. Sequence-specific N-substituted glycine "oligopeptoids" were utilized as substrates for azide-alkyne cycloaddition reactions. Diverse groups, including nucleobases and fluorophores, were conjugated at up to six positions on peptoid side chains with yields ranging from 88 to 96%. This strategy will be broadly applicable for generating polyvalent displays on peptides and other scaffolds, allowing precise control of spacing between the displayed groups.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Combinatorial Chemistry Techniques
  • Cyclization
  • Glycine / analogs & derivatives*
  • Glycine / chemistry*
  • Models, Molecular*
  • Molecular Mimicry
  • Molecular Structure
  • Peptoids / chemical synthesis*
  • Peptoids / chemistry*


  • Peptoids
  • Glycine