Citation: Yingxiao Gao, Feng Feng, Ting Luo, Yusong Han, Mingxuan Wu. Development of site-selective photo crosslinking between tyrosine and sulfonium in methyllysine readers[J]. Chinese Chemical Letters, ;2025, 36(10): 110756. doi: 10.1016/j.cclet.2024.110756 shu

Development of site-selective photo crosslinking between tyrosine and sulfonium in methyllysine readers

Yingxiao Gao ^a ,
Feng Feng ^{b, c} ,
Ting Luo ^b ,
Yusong Han ^b ,
Mingxuan Wu ^{b, c, d, *,}

a.
Department of Chemistry, Fudan University, Shanghai 200438, China
b.
Department of Chemistry, School of Science, Westlake University, Hangzhou 310030, China
c.
Westlake Laboratory of Life Sciences and Biomedicine, Hangzhou 310024, China
d.
Institute of Natural Sciences, Westlake Institute for Advanced Study, Hangzhou 310024, China

wumingxuan@westlake.edu.cn

Received Date: 10 September 2024
Revised Date: 2 December 2024
Accepted Date: 11 December 2024
Available Online: 12 December 2024

Figures(4)

Reader proteins that bind specific methyllysine are important to biological functions of lysine methylation, but readers of many methyllysine sites are still unknown. Therefore, development of covalent probes is important to identify readers from cell samples so as to understand biological roles of lysine methylation. Generally, readers bind methyllysine via aromatic cages that contain tryptophan, tyrosine and phenylalanine, that offer a unique motif for selective crosslinking. We recently reported a site-selective tryptophan crosslinking strategy based on dimethylsulfonium that mimics dimethyllysine to crosslink tryptophan in aromatic cages of readers. Since tyrosine is a key residue for binding affinity to methyllysine, especially some readers that do not contain tryptophan residues in the binding pocket. Here we developed strategies of site-selective crosslinking to tyrosine. Ultraviolet (UV) source was applied to excite tyrosine at neutral pH or phenoxide at basic pH, and subsequent single-electron transfer (SET) from Tyr* to sulfonium inside the binding pocket enables selective crosslinking. In consequence, methyllysine readers with tyrosine-containing aromatic cages could be selectively crosslinked by site-specific sulfonium peptide probes. In addition, we expanded substrates from aromatic cages to tyrosine residues of proximate contact with sulfonium probes. The pair of LgBiT and SmBiT exhibited orthogonal crosslinking in complicated cell samples. As a result, we may expand sulfonium tools to target local tyrosine in future investigations.
- Lysine methylation,
- Methyllysine readers,
- Dimethylsulfonium,
- Tyrosine,
- Site-selective crosslinking
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