Organic and Biomolecular Chemistry p. 3610 - 3614 (2018)
Update date:2022-07-30
Topics:
Sun, Yao
Lyu, Zhenbin
Wang, Zhiqiang
Zeng, Xiaodong
Zhou, Hui
Xu, Fuchun
Chen, Ziyang
Xu, Yuling
Xu, Ping
Hong, Xuechuan
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.
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