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N -Terminal Cysteine Bioconjugation with (2-Cyanamidophenyl)boronic Acids Enables the Direct Formation of Benzodiazaborines on Peptides.

Rita PadanhaRafaela A N CavadasPedro MerinoJoão P M AntónioPedro M P Gois
Published in: Organic letters (2023)
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.
Keyphrases
  • amino acid
  • living cells
  • single molecule