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Issue 19, 2018
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Facile Cu(ii)-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions

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Abstract

The bioconjugation of peptide derivatives such as polypeptides, peptide-based probes and proteins is a vibrant area in many scientific fields. However, reports on metal-mediated chemical methods towards native peptides especially non-engineering protein modification under mild conditions are still limited. Herein, we describe a novel Cu(II)-mediated strategy for the conjugation of thioesters/thioacids to peptides under mild conditions with high functional group tolerance. Based on this strategy, polypeptides, even peptide-based fluorescent probes, can be efficiently constructed. Finally, the selective modification of lysine residues of native Ub with thioesters could be realized and complete conjugation of Ub could be achieved even under equivalent Cu(II). These promising results could greatly expand Cu(II)-mediated reaction strategies on chemical biology and molecular imaging.

Graphical abstract: Facile Cu(ii)-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions

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Supplementary files

Article information


Submitted
03 Mar 2018
Accepted
18 Apr 2018
First published
19 Apr 2018

Org. Biomol. Chem., 2018,16, 3610-3614
Article type
Paper

Facile Cu(II)-mediated conjugation of thioesters and thioacids to peptides and proteins under mild conditions

Y. Sun, Z. Lyu, Z. Wang, X. Zeng, H. Zhou, F. Xu, Z. Chen, Y. Xu, P. Xu and X. Hong, Org. Biomol. Chem., 2018, 16, 3610
DOI: 10.1039/C8OB00536B

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