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

Kwan, TT-L and Boutureira, O and Frye, EC and Walsh, SJ and Gupta, MK and Wallace, S and Wu, Y and Zhang, F and Sore, HF and Galloway, WRJD and Chin, JW and Welch, M and Bernardes, GJL and Spring, DR (2017) Protein modification via alkyne hydrosilylation using a substoichiometric amount of ruthenium(II) catalyst. Chemical Science, 8. pp. 3871-3878. ISSN 2041-6520

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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 $\textit{O}$-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 $\textit{gem}$-disubstituted vinylsilane linkage can be further elaborated through thiol–ene coupling or fluoride-induced protodesilylation, demonstrating its utility in further rounds of targeted modifications.

Item Type: Article
Subjects: UNSPECIFIED
Divisions: UNSPECIFIED
Depositing User: Cron Job
Date Deposited: 25 Jun 2019 02:47
Last Modified: 15 Apr 2021 07:01
DOI: 10.1039/c6sc05313k