Click chemistry as a macrocyclization tool in the solid-phase synthesis of small cyclic peptides

Org Lett. 2007 Nov 22;9(24):5011-4. doi: 10.1021/ol702228u. Epub 2007 Oct 23.

Abstract

Despite the vast number of techniques developed for the cyclization of small peptides, cyclization efficiency remains problematic in peptides that lack turn-promoting structures. Here we demonstrate the utility of click chemistry as a macrocyclization tool in the solid-phase synthesis of cyclic tetra-, penta-, hexa-, and heptapeptides. On-resin cyclization is completed at room temperature within 6 h, resulting in predominantly monomer with small amounts of cyclomultimer byproducts.

Publication types

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

MeSH terms

  • Combinatorial Chemistry Techniques / methods*
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Conformation
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Stereoisomerism
  • Time Factors

Substances

  • Peptides, Cyclic