Cleavable and tunable cysteine-specific arylation modification with aryl thioethers.

ABSTRACT: Cysteine represents an attractive target for peptide/protein modification due to the intrinsic high nucleophilicity of the thiol group and low natural abundance. Herein, a cleavable and tunable covalent modification approach for cysteine containing peptides/proteins with our newly designed aryl thioethers via a S _N Ar approach was developed. Highly efficient and selective bioconjugation reactions can be carried out under mild and biocompatible conditions. A series of aryl groups bearing different bioconjugation handles, affinity or fluorescent tags are well tolerated. By adjusting the skeleton and steric hindrance of aryl thioethers slightly, the modified products showed a tunable profile for the regeneration of the native peptides.

SUBMITTER: Li J 

PROVIDER: S-EPMC8179606 | biostudies-literature | 2021 Feb

REPOSITORIES: biostudies-literature