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Issue 26, 2019
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Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols

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Abstract

A series of dicopper azacryptand complexes was evaluated in copper-catalysed azide–alkyne cycloaddition (CuAAC) in water at 37 °C. It was found that they showed high activity at concentrations as low as 5 μM. These dinuclear catalysts were more susceptible toward inhibition by cysteine rather than glutathione under the conditions tested. Interestingly, the mononuclear copper complexes that are ligated by tripodal amine ligands, also exhibited good catalytic activity in aqueous media and showed similar sensitivity toward biological thiols as that of the dinuclear complexes. Our results suggest that the azacryptand catalysts are too structurally flexible to adequately prevent interactions of their metal centres with external nucleophiles. However, further steric tuning of the ligand structure might enable more effective substrate gating in future studies.

Graphical abstract: Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols

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Supplementary files

Article information


Submitted
17 Feb 2019
Accepted
09 Apr 2019
First published
09 Apr 2019

Dalton Trans., 2019,48, 9751-9758
Article type
Paper

Evaluation of dicopper azacryptand complexes in aqueous CuAAC reactions and their tolerance toward biological thiols

T. V. Tran, G. Couture and L. H. Do, Dalton Trans., 2019, 48, 9751
DOI: 10.1039/C9DT00724E

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