ArticleChemistry (Weinheim an der Bergstrasse, Germany)2025
An Efficient Thiol-ene Mediated Protocol for Thiolated Peptide Synthesis and On-Resin Diversification.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
The unique nucleophilic and redox properties of the sulfhydryl group render it highly useful as a synthetic handle for the diversification of peptide structure, including macrocyclization, ligation, and bioconjugation. Herein, a sequential acyl-thiol-ene/S-deacetylation protocol for selectively installing thiol residues onto bioactive peptides on-resin is demonstrated. Through judicious placement of appropriate unsaturated residues, the hydrothiolation/S-deacetylation protocol offers a novel synthetic strategy to investigate the structure-activity relationship of disulfide-containing peptides displaying different ring sizes. Furthermore, a new and generally applicable fluorescent labeling strategy is introduced to facilitate direct on-resin conjugation without intermediate purification steps. These new methods provide a robust and versatile platform for peptide macrocyclization and bioconjugation, with broad applications in peptide synthesis and chemical biology.
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