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Updated: Dec 22, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Microwave-assisted cleavage of cysteine perfluoroaryl thioethers
Taylor N Bednar1,2, Alissa R Resnikoff1,3, Jason Gavenonis4
1Department of Chemistry, Dickinson College, 28 North College Street, Carlisle, PA, 17013, USA.
Abstract:
The cysteine- perfluoroarene SNAr 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.
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