Site-selective chemical modification of biomolecules is a powerful tool to study and modulate their function both in vivo and in vitro. Hydrosilylation is an attractive way to install these modifications via stable carbon-silicon bonds. In organic synthesis, this reaction provides the most straightforward, atom-economical access to vinylsilanes, and their participation in Pd-catalysed cross-coupling and electrophilic substitution reactions are of significant importance.Despite reports on hydrosilylation in aqueous conditions, they are inapplicable in a biological setting due to the minimal water-solubility of the reported reagents. These limitations highlight the challenges for chemical modification of biomolecules via aqueous hydrosilylation.Herein, we report the synthesis and hydrosilylation of water-soluble hydrosilanes and alkynes in physiological conditions. The reaction's viability for biomolecule modification was also demonstrated via the selective labeling of terminal-alkyne modified lysozyme and superfolder green fluorescent protein with hydrosilane derivatives.

Aqeuous hydrosilylation: Application to site-selective protein modification

248th National Meeting (2014)

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