Click Chemistry for Cyclic Peptide Drug Design

Methods Mol Biol. 2019:2001:133-145. doi: 10.1007/978-1-4939-9504-2_8.

Abstract

Click chemistry is a powerful tool in constraining peptides into their active conformations. This chapter presents recent advancements involving the use of copper-catalyzed [3 + 2] azide-alkyne cycloaddition (CuAAC), better known as "click reaction" in the design and synthesis of cyclic peptide and cyclic peptidomimetic compounds. The usage of "click chemistry" reactions includes various topics: (a) mimicking peptide bonds; (b) synthesis of ordered structures; (c) ligation of peptidomimetic scaffolds; and most importantly in this chapter (d) cyclization of peptidomimetic scaffolds using the triazole ring as constraint of conformation.

Keywords: Click chemistry; Cyclic peptide; Peptide cyclization; Triazole.

MeSH terms

  • Alkynes / chemistry
  • Azides / chemistry
  • Biomimetics
  • Click Chemistry / methods*
  • Copper / chemistry
  • Cyclization
  • Cycloaddition Reaction
  • Drug Design
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / metabolism
  • Protein Conformation, alpha-Helical
  • Protein Conformation, beta-Strand
  • Triazoles / chemistry

Substances

  • Alkynes
  • Azides
  • Peptides, Cyclic
  • Triazoles
  • Copper