Peptide conjugation via CuAAC 'click' chemistry

Abdullah A H Ahmad Fuaad, Fazren Azmi, Mariusz Skwarczynski, Istvan Toth

Research output: Contribution to journalArticle

55 Citations (Scopus)

Abstract

The copper (I)-catalyzed alkyne azide 1,3-dipolar cycloaddition (CuAAC) or 'click' reaction, is a highly versatile reaction that can be performed under a variety of reaction conditions including various solvents, a wide pH and temperature range, and using different copper sources, with or without additional ligands or reducing agents. This reaction is highly selective and can be performed in the presence of other functional moieties. The flexibility and selectivity has resulted in growing interest in the application of CuAAC in various fields. In this review, we briefly describe the importance of the structural folding of peptides and proteins and how the 1,4-disubstituted triazole product of the CuAAC reaction is a suitable isoster for an amide bond. However the major focus of the review is the application of this reaction to produce peptide conjugates for tagging and targeting purpose, linkers for multifunctional biomacromolecules, and reporter ions for peptide and protein analysis.

Original languageEnglish
Pages (from-to)13148-13174
Number of pages27
JournalMolecules
Volume18
Issue number11
DOIs
Publication statusPublished - Nov 2013
Externally publishedYes

Fingerprint

Click Chemistry
conjugation
peptides
chemistry
Peptides
Copper
Triazoles
Alkynes
Azides
Cycloaddition
Protein Folding
Reducing Agents
Cycloaddition Reaction
Amides
Proteins
Ions
Ligands
proteins
copper
Temperature

Keywords

  • Chemical ligation
  • Click chemistry
  • CuAAC
  • Peptide ligation

ASJC Scopus subject areas

  • Organic Chemistry
  • Medicine(all)

Cite this

Ahmad Fuaad, A. A. H., Azmi, F., Skwarczynski, M., & Toth, I. (2013). Peptide conjugation via CuAAC 'click' chemistry. Molecules, 18(11), 13148-13174. https://doi.org/10.3390/molecules181113148

Peptide conjugation via CuAAC 'click' chemistry. / Ahmad Fuaad, Abdullah A H; Azmi, Fazren; Skwarczynski, Mariusz; Toth, Istvan.

In: Molecules, Vol. 18, No. 11, 11.2013, p. 13148-13174.

Research output: Contribution to journalArticle

Ahmad Fuaad, AAH, Azmi, F, Skwarczynski, M & Toth, I 2013, 'Peptide conjugation via CuAAC 'click' chemistry', Molecules, vol. 18, no. 11, pp. 13148-13174. https://doi.org/10.3390/molecules181113148
Ahmad Fuaad AAH, Azmi F, Skwarczynski M, Toth I. Peptide conjugation via CuAAC 'click' chemistry. Molecules. 2013 Nov;18(11):13148-13174. https://doi.org/10.3390/molecules181113148
Ahmad Fuaad, Abdullah A H ; Azmi, Fazren ; Skwarczynski, Mariusz ; Toth, Istvan. / Peptide conjugation via CuAAC 'click' chemistry. In: Molecules. 2013 ; Vol. 18, No. 11. pp. 13148-13174.
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