Amide Chemistry Enables Redox Locking of Cyclic Disulfides for Polypeptide Assembly.

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 applicati

SUBMITTER: Diemer V 

PROVIDER: S-EPMC12363628 | biostudies-literature | 2025 Aug

REPOSITORIES: biostudies-literature