Conditional Copper-Catalyzed Azide–Alkyne Cycloaddition by Catalyst Encapsulation

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Abstract

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
Volume59
Issue number24
DOIs
Publication statusPublished - 2020

Keywords

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

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