Bioorthogonal chemistry offers a powerful mechanism for chemically interfacing with biomolecules. For two decades, a primary focus of this field has been the development of associative transformations highlighted by bioorthogonal ligation or “click” reactions facilitating the attachment of probes, drugs, and affinity handles to a variety of biomolecules. More recently, bioorthogonal dissociative reactions have been developed for cellular protein activation/inactivation applications and for the development of drug delivery platforms. We describe a paired set of bioorthogonal click and release reactions involving enamine <i>N</i>-oxides and show how the bioorthogonal formation and breakdown of this motif can be used in target identification and other biological applications.

Expanding the functional repertoire of bioorthogonal chemistry

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