Protein modification: Via alkyne hydrosilylation using a substoichiometric amount of ruthenium(II) catalyst

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Abstract

Transition metal catalysis has emerged as a powerful strategy to expand synthetic flexibility of protein modification. Herein, we report a cationic Ru(ii) system that enables the first example of alkyne hydrosilylation between dimethylarylsilanes and O-propargyl-functionalized proteins using a substoichiometric amount or low-loading of Ru(ii) catalyst to achieve the first C-Si bond formation on full-length substrates. The reaction proceeds under physiological conditions at a rate comparable to other widely used bioorthogonal reactions. Moreover, the resultant gem-disubstituted vinylsilane linkage can be further elaborated through thiol-ene coupling or fluoride-induced protodesilylation, demonstrating its utility in further rounds of targeted modifications.

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Kwan, T. T. L., Boutureira, O., Frye, E. C., Walsh, S. J., Gupta, M. K., Wallace, S., … Spring, D. R. (2017). Protein modification: Via alkyne hydrosilylation using a substoichiometric amount of ruthenium(II) catalyst. Chemical Science, 8(5), 3871–3878. https://doi.org/10.1039/c6sc05313k

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