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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.

Graphical abstract: Protein modification via alkyne hydrosilylation using a substoichiometric amount of ruthenium(ii) catalyst

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Publication details

The article was received on 04 Dec 2016, accepted on 04 Mar 2017 and first published on 14 Mar 2017


Article type: Edge Article
DOI: 10.1039/C6SC05313K
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    Protein modification via alkyne hydrosilylation using a substoichiometric amount of ruthenium(II) catalyst

    T. T.-L. Kwan, O. Boutureira, E. C. Frye, S. J. Walsh, M. K. Gupta, S. Wallace, Y. Wu, F. Zhang, H. F. Sore, W. R. J. D. Galloway, J. W. Chin, M. Welch, G. J. L. Bernardes and D. R. Spring, Chem. Sci., 2017, Advance Article , DOI: 10.1039/C6SC05313K

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