<i>N</i>-Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides
Rita Padanha, Rafaela A. N. Cavadas, Pedro Merino, João P. M. António, Pedro M. P. Góis
Abstract
High Resolution Image Download MS PowerPoint Slide Benzodiazaborines (BDABs) have emerged as a valuable tool to produce stable and functional bioconjugates via a click-type transformation. However, the current available methods to install them on peptides lack bioorthogonality, limiting their applications. Here, we report a strategy to install BDABs directly on peptide chains using (2-cyanamidophenyl)boronic acids (2CyPBAs). The resulting BDAB is stabilized through the formation of a key intramolecular B–N bond. This technology was applied in the selective modification of N -terminal cysteine-containing functional peptides.
Topics & Concepts
ChemistryBioconjugationCysteineBoronic acidIntramolecular forceCombinatorial chemistryPeptideLimitingAmino acidStereochemistryBiochemistryEnzymeEngineeringMechanical engineeringClick Chemistry and ApplicationsChemical Synthesis and AnalysisPeptidase Inhibition and Analysis