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 language | English |
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Pages (from-to) | 9340-9344 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 59 |
Issue number | 24 |
DOIs | |
State | Published - 8 Jun 2020 |
Bibliographical note
Publisher Copyright:© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Keywords
- catalysis
- click chemistry
- cucurbit[n]uril
- host–guest systems
- protein labeling