Fit to be tied: conformation-directed macrocyclization of peptoid foldamers

Org Lett. 2007 Aug 16;9(17):3275-8. doi: 10.1021/ol071169l. Epub 2007 Jul 18.


Covalent macrocyclic constraints can be readily installed on N-substituted glycine "peptoid" oligomer substrates. Cu(I)-catalyzed [3+2] cycloaddition reactions were conducted on solid support to ligate peptoid side chain azide and alkyne functionalities. Intramolecular macrocycle formation is facilitated by preorganizing the reactive groups across one turn of the helical secondary structure. These results confirm that conformational ordering can be exploited to assist the macrocyclization of folded oligomers.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Cyclization
  • Macrocyclic Compounds / chemical synthesis
  • Molecular Conformation
  • Peptoids / chemical synthesis*
  • Peptoids / chemistry
  • Protein Structure, Secondary


  • Macrocyclic Compounds
  • Peptoids