Tricks with clicks: Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition

Justin M. Holub, Kent Kirshenbaum

Research output: Contribution to journalArticle

Abstract

This tutorial review examines recent developments involving use of Copper-catalyzed Azide-Alkyne [3 + 2] Cycloaddition (CuAAC) reactions in the synthesis, modification, and conformational control of peptidomimetic oligomers. CuAAC reactions have been used to address a variety of objectives including: (i) ligation of peptidomimetic oligomers; (ii) synthesis of ordered "foldamer" architectures; (iii) conjugation of ligands to peptidomimetic scaffolds; and (iv) macrocyclization of peptidomimetics using triazole linkages as conformational constraints. Variations in synthesis protocols, such as the use of different solvent systems, temperatures and copper species are evaluated herein to present a range of variables for the optimization of CuAAC reactions. The overall objectives of these studies are assessed to highlight the widespread applications of the products, which range from bioactive ligands to new materials.

Original languageEnglish (US)
Pages (from-to)1325-1337
Number of pages13
JournalChemical Society Reviews
Volume39
Issue number4
DOIs
StatePublished - 2010

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Peptidomimetics
Alkynes
Azides
Cycloaddition
Oligomers
Copper
Ligands
Triazoles
Scaffolds
Temperature

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Tricks with clicks : Modification of peptidomimetic oligomers via copper-catalyzed azide-alkyne [3 + 2] cycloaddition. / Holub, Justin M.; Kirshenbaum, Kent.

In: Chemical Society Reviews, Vol. 39, No. 4, 2010, p. 1325-1337.

Research output: Contribution to journalArticle

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