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

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.

SUBMITTER: Tilden JAR

PROVIDER: S-EPMC9305290 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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

Tilden James A R JAR Lubben Anneke T AT Reeksting Shaun B SB Kociok-Köhn Gabriele G Frost Christopher G CG

Chemistry (Weinheim an der Bergstrasse, Germany) 20220112 11

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 b ...[more]

PMID: 34905636

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