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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

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

Li Jian J Deng Jun-Jie JJ Yin Zhibin Z Hu Qi-Long QL Ge Yang Y Song Zhendong Z Zhang Ying Y Chan Albert S C ASC Li Huilin H Xiong Xiao-Feng XF

Chemical science 20210218 14

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 ary ...[more]

PMID: 34168774

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