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Pd(II)‐Mediated C−H Activation for Cysteine Bioconjugation
Author(s) -
Tilden James A. R.,
Lubben Anneke T.,
Reeksting Shaun B.,
KociokKöhn Gabriele,
Frost Christopher G.
Publication year - 2022
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202104385
Subject(s) - bioconjugation , chemistry , cysteine , biomolecule , combinatorial chemistry , residue (chemistry) , ligand (biochemistry) , peptide , nanotechnology , biochemistry , materials science , enzyme , receptor
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.