Boronic Acid Pairs for Sequential Bioconjugation
Mary K. Miller, Michael J. Swierczynski, Yuxuan Ding, Zachary T. Ball
Abstract
Boronic acids can play diverse roles when applied in biological environments, and employing boronic acid structures in tandem could provide new tools for multifunctional probes. This Letter describes a pair of boronic acid functional groups, 2-nitro-arylboronic acid (NAB) and (E)-alkenylboronic acid (EAB), that enable sequential cross-coupling through stepwise nickel- and copper-catalyzed processes. The selective coupling of NAB groups enables the preparation of stapled peptides, protein–protein conjugates, and other bioconjugates.
Topics & Concepts
Boronic acidChemistryBioconjugationTandemCombinatorial chemistryConjugateMathematical analysisMaterials scienceComposite materialMathematicsPeptidase Inhibition and AnalysisChemical Synthesis and AnalysisClick Chemistry and Applications