Click-to-release bioorthogonal tyrosine modification

Abstract

Bioorthogonal chemistry is an emerging field that facilitates selective chemical reactions in physiological conditions. A particularly promising approach is tetrazine-isonitrile chemistry, noted for its ability to enable click-to-release reactions for phenols. This study presents the synthesis and NMR characterization of a tetrazine-modified tyrosine substrate and explores an isonitrile to induce a dissociative bioorthogonal reaction that liberates the unmodified substrate. This system holds potential for diverse applications in life sciences, including drug delivery and fluorescent labeling.