A bifunctional vinyl-sulfonium tethered peptide induced by thio-Michael-type addition reaction

Autor:	Zhanfeng Hou, Yang Li, Rui Wang, Chenshan Lian, Feng Yin, Xuan Qin, Xiaofeng Ding, Zigang Li, Ziyuan Zhou, Hailing Chen, Chuan Wan, Yaping Zhang, Hongkun Xu
Rok vydání:	2022
Předmět:	chemistry.chemical_classification Addition reaction Chemistry Sulfonium technology industry and agriculture Thio Peptide General Chemistry Combinatorial chemistry chemistry.chemical_compound Residue (chemistry) Nucleophile Target protein Cysteine
Zdroj:	Chinese Chemical Letters. 33:2001-2004
ISSN:	1001-8417
Popis:	The modification and functionalization of peptides is of great significance in modern biotechnology and drug development. Here we report a highly reactive Michael-type warhead for the covalently modification of cysteine on peptide and protein. By installing a vinyl group onto a methionine residue of peptide, the produced vinyl sulfonium can be efficiently nucleophilic added by appropriate cysteine residue of this peptide, and thus yield a cyclized peptide. This peptide cyclization strategy was proven to exhibit improved cell penetration and good stability. Moreover, a peptide ligand bearing vinyl sulfonium could covalently bind to the cysteine in the target protein, indicating the potential of vinyl sulfonium as a novel warhead for developing covalent peptide inhibitor.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::52a3c964f9f72968db984f9646806a2d https://doi.org/10.1016/j.cclet.2021.09.071 Zobrazit plný text záznamu Full Text from ScienceDirect