Electrophilic groups that undergo sulfur-exchange chemistry with protein nucleophiles can serve as the functional basis of chemical proteomic probes. A new addition to this class, sulfuramidimidoyl fluoride (SAF), which can be included in an array of covalent small molecule probes, exhibits a unique reactivity profile with proteins.
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References
Dong, J., Krasnova, L., Finn, M. G. & Sharpless, K. B. Sulfur(vi) fluoride exchange (SuFEx): another good reaction for click chemistry. Angew. Chem. Int. Ed. Engl. 53, 9430–9448 (2014).
Brighty, G. J et al. Nat. Chem. https://doi.org/10.1038/s41557-020-0530-4 (2020).
Narayanan, A. & Jones, L. H. Sulfonyl fluorides as privileged warheads in chemical biology. Chem. Sci. 6, 2650–2659 (2015).
Mortenson, D. E. et al. “Inverse drug discovery” strategy to identify proteins that are targeted by latent electrophiles as exemplified by aryl fluorosulfates. J. Am. Chem. Soc. 140, 200–210 (2018).
Zhao, Q. et al. Broad-spectrum kinase profiling in live cells with lysine-targeted sulfonyl fluoride probes. J. Am. Chem. Soc. 139, 680–685 (2017).
Hahm, H. S. et al. Global targeting of functional tyrosines using sulfur–triazole exchange chemistry. Nat. Chem. Biol. 16, 150–159 (2020).
Zambaldo, C. et al. 2-Sulfonylpyridines as tunable, cysteine-reactive electrophiles. J. Am. Chem. Soc. 142, 8972–8979 (2020).
Motiwala, H. F., Kuo, Y. H., Stinger, B. L., Palfey, B. A. & Martin, B. R. Tunable heteroaromatic sulfones enhance in-cell cysteine profiling. J. Am. Chem. Soc. 142, 1801–1810 (2020).
Li, S., Wu, P., Moses, J. E. & Sharpless, K. B. multidimensional SuFEx click chemistry: sequential sulfur(vi) fluoride exchange connections of diverse modules launched from an SOF4 hub. Angew. Chem. Int. Ed. Engl. 56, 2903–2908 (2017).
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Speltz, T.E., Moellering, R.E. Protein targeting with SAF(er) electrophiles. Nat. Chem. 12, 885–887 (2020). https://doi.org/10.1038/s41557-020-00553-6
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DOI: https://doi.org/10.1038/s41557-020-00553-6