ArticleAngewandte Chemie (International ed. in English)2025
Amide Chemistry Enables Redox Locking of Cyclic Disulfides for Polypeptide Assembly.
Article in Angewandte Chemie (International ed. in English), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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Who cites it
1 citing paper in PubMed.
- Amide Chemistry Enables Redox Locking of Cyclic Disulfides for Polypeptide Assembly.Angewandte Chemie (International ed. in English) · 2025Article
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5 authors.
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Abstract
A practical strategy in synthetic organic chemistry for shutting down temporarily the nucleophilicity of thiols is to exploit their redox properties by converting them into disulfides. The stability of such a thiol protection in reductive medium can be sensitive to microenvironmental changes, including chemical modifications occurring nearby. Although difficult to achieve, large shifts in disulfide stability might provide a practical mean for bringing selectivity in a reacting system comprising multiple thiol functionalities. Here we report that the stability of a cyclic disulfide increases dramatically upon acylation of an amino group placed in the vicinity of the S─S bond. The gain in stability is so pronounced that the amide bond formation acts as a redox lock. We describe the application of such a redox switch to the chemoselective assembly of polypeptides by thiol-based peptide ligation chemistries.
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