The synthesis of palladium oxidative addition complexes of unprotected peptides is described. Incorporation of 4-halophenylalanine into a peptide during solid phase peptide synthesis allows for subsequent oxidative addition at this position of the unprotected peptide upon treatment with a palladium precursor and suitable ligand. The resulting palladium−peptide complexes are solid, storable, water-soluble, and easily purified via high-performance liquid chromatography. These complexes react rapidly with thiols at low micromolar concentrations in an aqueous buffer, offering an efficient method for bioconjugation. Using this strategy, peptides can be rapidly functionalized with small molecules to prepare modified aryl thioether side-chains. Additionally, peptide−peptide and peptide−protein ligations are demonstrated under dilute aqueous conditions.

Palladium−peptide oxidative addition complexes for bioconjugation

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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