Isolable Cysteine Sulfenyl Iodide: Stabilization by a Molecular Cradle, Crystal Structure, and Biologically Relevant Reactivity.

ABSTRACT: Cysteine sulfenyl iodides (Cys-SIs) have long been recognized as important intermediates in the oxidative modification of cysteine thiols since 1950s, implicated in pathways such as hydrolysis to cysteine sulfenic acid (Cys-SOH) and electrophilic aromatic substitution with an indole ring of tryptophan to form Cys-Trp thioether linkages. Despite their proposed significance in both biological and chemical contexts, direct examination of Cys-SIs has been precluded by their intrinsic instability. Herein, the first isolation of a small-molecule Cys-SI, stabilized using a nanosized molecular cradle at the N-terminus of cysteine, is reported. The structure of the isolable Cys-SI is determined by X-ray crystallography, and its reactivity is investigated with a range of nucleophiles. Hydrolysis to

SUBMITTER: Otaka S 

PROVIDER: S-EPMC12703442 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature