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Microwave-assisted cleavage of cysteine perfluoroaryl thioethers

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The cysteine- perfluoroarene S N Ar reaction allows for the sequence-specific attachment of dyes and affinity tags to peptides and proteins. However, while many methods exist for the desulfuration of… Click to show full abstract

The cysteine- perfluoroarene S N Ar reaction allows for the sequence-specific attachment of dyes and affinity tags to peptides and proteins. However, while many methods exist for the desulfuration of native and functionalized cysteine residues, there are no reports of their application to perfluoroarylated cysteines. Herein we report both the hydrogenolysis of a perfluoroarylated cysteine to alanine and elimination to dehydroalanine, reactions that are both accelerated by microwave irradiation.

Keywords: cysteine; microwave assisted; cleavage cysteine; cysteine perfluoroaryl; perfluoroaryl thioethers; assisted cleavage

Journal Title: Amino Acids
Year Published: 2020

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