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Synfacts 2017; 13(02): 0211
DOI: 10.1055/s-0036-1589850
DOI: 10.1055/s-0036-1589850
Polymer-Supported Synthesis
Azide–Alkyne Cycloaddition with a Melanin-Supported Copper(I) Catalyst
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
Recyclable Cu(I)/Melanin Dots for Cycloaddition, Bioconjugation and Cell Labelling.
Chem. Sci. 2016;
7: 5888-5892
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. Januar 2017 (online)
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).
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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.
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