Protein Modification via Alkyne Hydrosilylation Using A Substoichiometric Amount of Ruthenium(II) Catalyst

Terence T.-L Kwan, Omar Boutureira, Elizabeth C. Frye, Stephen J Walsh, Moni K Gupta, Stephen Wallace, Yuteng Wu, Fengzhi Zhang, Hannah F Sore, Warren R J D Galloway, Jason W Chin, Martin Welch, Gonçalo J.L. Bernardes, David R Spring

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

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.
Original languageEnglish
Pages (from-to)3871-3878
Number of pages8
JournalChemical Science
Volume8
Issue number5
Early online date14 Mar 2017
DOIs
Publication statusPublished - 1 May 2017

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