Pd(II)-Mediated C−H Activation for Cysteine Bioconjugation

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Abstract

Selective bioconjugation remains a significant challenge for the synthetic chemist due to the stringent reaction conditions required by biomolecules coupled with their high degree of functionality. The current trailblazer of transition-metal mediated bioconjugation chemistry involves the use of Pd(II) complexes prepared via an oxidative addition process. Herein, the preparation of Pd(II) complexes for cysteine bioconjugation via a facile C−H activation process is reported. These complexes show bioconjugation efficiency competitive with what is seen in the current literature, with a user-friendly synthesis, common Pd(II) sources, and a more cost-effective ligand. Furthermore, these complexes need not be isolated, and still achieve high conversion efficiency and selectivity of a model peptide. These complexes also demonstrate the ability to selectively arylate a single surface cysteine residue on a model protein substrate, further demonstrating their utility.

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Tilden, J. A. R., Lubben, A. T., Reeksting, S. B., Kociok-Köhn, G., & Frost, C. G. (2022). Pd(II)-Mediated C−H Activation for Cysteine Bioconjugation. Chemistry - A European Journal, 28(11). https://doi.org/10.1002/chem.202104385

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