Intermolecular sulfur atom transfer cascade enabled late-stage introduction of sulfilimines into peptides.

ABSTRACT: Sulfilimines, a privileged class of -S(iv)[double bond, length as m-dash]N- functional groups found in nature, have been exploited as valuable building blocks in organic synthesis and as pharmacophores in drug discovery, and have aroused significant interest in the chemical community. Nevertheless, strategies for late-stage introduction of sulfilimines into peptides and proteins have still met with limited success. Herein, we have developed a method of introducing biological sulfilimine fragments into peptides by an intermolecular sulfur atom transfer cascade reaction, utilizing hydroxylamine condensed with the acid moieties of peptides and varied diaryl disulfides. It provides a convenient, efficient, metal-free and widely applicable method for late-stage modification and functionalizatio

SUBMITTER: He Z 

PROVIDER: S-EPMC11425069 | biostudies-literature | 2024 Sep

REPOSITORIES: biostudies-literature