Citation: Hongkun Xu, Xuan Qin, Yaping Zhang, Chuan Wan, Rui Wang, Zhanfeng Hou, Xiaofeng Ding, Hailing Chen, Ziyuan Zhou, Yang Li, Chenshan Lian, Feng Yin, Zigang Li. A bifunctional vinyl-sulfonium tethered peptide induced by thio-Michael-type addition reaction[J]. Chinese Chemical Letters, ;2022, 33(4): 2001-2004. doi: 10.1016/j.cclet.2021.09.071 shu

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

Hongkun Xu ^{a, 1} ,
Xuan Qin ^{a, 1} ,
Yaping Zhang ^{a, 1} ,
Chuan Wan ^a ,
Rui Wang ^b ,
Zhanfeng Hou ^b ,
Xiaofeng Ding ^c ,
Hailing Chen ^a ,
Ziyuan Zhou ^{a, d} ,
Yang Li ^a ,
Chenshan Lian ^b ,
Feng Yin ^{b, *,} ,
Zigang Li ^{a, b, *,}

a.
State Key Laboratory of Chemical Oncogenomics, School of Chemical Biology and Biotechnology, Peking University Shenzhen Graduate School, Shenzhen 518055, China
b.
Pingshan translational medicine center, Shenzhen Bay Laboratory, Shenzhen 518055, China
c.
Anhui Medical University, Hefei 230032, China
d.
Cancer Hospital Chinese Academy of Medical Sciences, Shenzhen Center, Shenzhen 518000, China

yinfeng@pkusz.edu.cn

lizg@pkusz.edu.cn

Received Date: 1 July 2021
Revised Date: 12 September 2021
Accepted Date: 22 September 2021
Available Online: 26 September 2021

Figures(5)

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.
- Vinyl sulfonium,
- Michael-type addition,
- Peptide cyclization,
- Covalent peptide inhibitor,
- Proximity-induced ligation
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