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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.

SUBMITTER: Kwan TT 

PROVIDER: S-EPMC5578368 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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Protein modification <i>via</i> alkyne hydrosilylation using a substoichiometric amount of ruthenium(ii) catalyst.

Kwan Terence T-L TT   Boutureira Omar O   Frye Elizabeth C EC   Walsh Stephen J SJ   Gupta Moni K MK   Wallace Stephen S   Wu Yuteng Y   Zhang Fengzhi F   Sore Hannah F HF   Galloway Warren R J D WRJD   Chin Jason W JW   Welch Martin M   Bernardes Gonçalo J L GJL   Spring David R DR  

Chemical science 20170314 5

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 <i>O</i>-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 comparab  ...[more]

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