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Updated: Aug 5, 2026

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
Regiochemical Control in a Thiol-Epoxy 'Click' Reaction: Synthesis of Cysteine and Glutathione Chain-End
Oana Grad1, Crina Socaci1, Mihaela Diana Lazar1
1National Institute for Research and Development of Isotopic and Molecular Technologies-INCDTIM, 67-103 Donat Street, 400293 Cluj-Napoca, Romania.
Abstract:
The cysteine-based thiol-epoxy 'click' reaction is demonstrated as an efficient and practical approach for the synthesis of zwitterionic structures. The transformation employs unprotected cysteine, proceeds in aqueous media, and affords quantitative conversions. Notably, acid- and base-catalyzed conditions provide exclusive access to different cysteine-based thioether regioisomers in aqueous conditions. The pH-responsive behavior of the resulting zwitterions is further elucidated by NMR spectroscopy. Finally, the synthetic strategy is extended to the preparation of cysteine- and glutathione-functionalized polyethylene glycol polymers, showcasing its utility for the preparation of amino acid-/peptide-containing macromolecular materials.
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