Issue 5, 2017

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
04 Dec 2016
Accepted
04 Mar 2017
First published
14 Mar 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2017,8, 3871-3878

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, 8, 3871 DOI: 10.1039/C6SC05313K

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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