Conditional Copper-Catalyzed Azide–Alkyne Cycloaddition by Catalyst Encapsulation

Research output: Contribution to journalArticleScientificpeer-review

23 Downloads (Pure)


Supramolecular encapsulation is known to alter chemical properties of guest molecules. We have applied this strategy of molecular encapsulation to temporally control the catalytic activity of a stable copper(I)–carbene catalyst. Encapsulation of the copper(I)–carbene catalyst by the supramolecular host cucurbit[7]uril (CB[7]) resulted in the complete inactivation of a copper-catalyzed alkyne–azide cycloaddition (CuAAC) reaction. The addition of a chemical signal achieved the near instantaneous activation of the catalyst, by releasing the catalyst from the inhibited CB[7] catalyst complex. To broaden the scope of our on-demand CuAAC reaction, we demonstrated the protein labeling of vinculin with the copper(I)–carbene catalyst, to inhibit its activity by encapsulation with CB[7] and to initiate labeling at any moment by adding a specific signal molecule. Ultimately, this strategy allows for temporal control over copper-catalyzed click chemistry, on small molecules as well as protein targets.

Original languageEnglish
Pages (from-to)9340-9344
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number24
Publication statusPublished - 2020


  • catalysis
  • click chemistry
  • cucurbit[n]uril
  • host–guest systems
  • protein labeling

Fingerprint Dive into the research topics of 'Conditional Copper-Catalyzed Azide–Alkyne Cycloaddition by Catalyst Encapsulation'. Together they form a unique fingerprint.

  • Cite this