A Three-Component Organometallic Tyrosine Bioconjugation

Metal-based bioconjugation linkages represent a little-studied approach to protein functionalization that provides novel reactivity, stability, and function. Described is an organometallic bioconjugation, employing rhodium(III) salts, to link boronic acids with tyrosine residues by an arene complex. Both peptides and proteins are amenable to the mild bioconjugation in aqueous media, allowing incorporation of useful functionalities, such as affinity handles or fluorophores. Because of the metastability of the inorganic linkage, the conjugates are susceptible to cleavage by nucleophilic redox mediators but are stable toward typical biological conditions.