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

Autor: Kwan, TT-L, Boutureira, O, Frye, EC, Walsh, SJ, Gupta, MK, Wallace, S, Wu, Y, Zhang, F, Sore, HF, Galloway, WRJD, Chin, JW, Welch, M, Bernardes, GJL, Spring, DR
Jazyk: angličtina
Předmět:
Popis: 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.
Databáze: OpenAIRE