Sun Y, Hong S, Ma X, Cheng K, Wang J, Zhang Z, Yang M, Jiang Y, Hong X, * Cheng Z.
* Stanford University, USA; Wuhan University and Peking Union Medical College Hospital,
Beijing, P. R. of China
Recyclable Cu(I)/Melanin Dots for Cycloaddition, Bioconjugation and Cell Labelling.
Chem. Sci. 2016;
7: 5888-5892
Key words
copper - azides - alkynes - triazoles - click chemistry
Significance
A copper(I) catalyst supported on poly(ethylene glycol) (PEG) grafted melanin granules
[Cu(I)/M-dots], prepared by the method shown in eq. 1, catalyzed an azide–alkyne cycloaddition
in phosphate-buffered saline at room temperature during 30 minutes to give the corresponding
triazoles in ≤95% yield (eq. 2).
Comment
In the azide–alkyne cycloaddition of amino-PEG3 azide with ethynylbenzene, the Cu(I)/M-dots catalyst was recovered by centrifugation
and reused six times without significant loss of its catalytic activity. The Cu(I)/M-dots-catalyzed
azide–alkyne cycloaddition was also used in bioconjugation and cell labeling.
