Chemoselective umpolung of thiols to episulfoniums for cysteine bioconjugation.

ABSTRACT: Cysteine conjugation is an important tool in protein research and relies on fast, mild and chemoselective reactions. Cysteinyl thiols can either be modified with prefunctionalized electrophiles, or converted into electrophiles themselves for functionalization with selected nucleophiles in an independent step. Here we report a bioconjugation strategy that uses a vinyl thianthrenium salt to transform cysteine into a highly reactive electrophilic episulfonium intermediate in situ, to enable conjugation with a diverse set of bioorthogonal nucleophiles in a single step. The reactivity profile can connect several nucleophiles to biomolecules through a short and stable ethylene linker, ideal for introduction of infrared labels, post-translational modifications or NMR probes. In the absence of rea

SUBMITTER: Hartmann P 

PROVIDER: S-EPMC10914617 | biostudies-literature | 2024 Mar

REPOSITORIES: biostudies-literature