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Updated: Dec 3, 2025

Constructing Thioether/Vinyl Sulfide-tethered Helical Peptides Via Photo-induced Thiol-ene/yne Hydrothiolation
Published on: August 1, 2018
A modular template for the design of thiol-triggered sensors and prodrugs
Jessica Renee Knight1, Yingying Wang1, Shi Xu2
1Department of Chemistry, Washington State University, Pullman, WA 99164, USA.
Abstract:
A unique reaction between thiols (RSH) and alkyl sulfonylbenzothiazole was discovered. This reaction was specific for thiols and produced a sulfinic acid (RSO2H) as the intermediate, which further triggered an intramolecular cyclization to release a -OH containing payload. This reaction was used to develop thiol-triggered fluorescent sensors and prodrugs. The modular design of this template provides tunability of the release profiles of the payloads.
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