Jump to main content
Jump to site search


Rapid nickel(II)-promoted cysteine S-arylation with arylboronic acids

Author affiliations

Abstract

S-Arylation of cysteine residues is an increasingly powerful tool for site-specific modification of proteins, providing novel structure and electronic perturbation. The present work demonstrates an operationally-simple cysteine arylation reaction 2-nitro-substituted arylboronic acids, promoted by a simple nickel(II) salt. The process exhibits strikingly fast reaction rates under physiological conditions in purely aqueous media with excellent selectivity toward cysteine residues. Cysteine arylation of natural proteins and peptides allows attachment of useful reactive handles for stapling, imaging, or further conjugation.

Graphical abstract: Rapid nickel(ii)-promoted cysteine S-arylation with arylboronic acids

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Jan 2019, accepted on 02 Feb 2019 and first published on 04 Feb 2019


Article type: Communication
DOI: 10.1039/C9CC00159J
Citation: Chem. Commun., 2019, Advance Article

  •   Request permissions

    Rapid nickel(II)-promoted cysteine S-arylation with arylboronic acids

    K. Hanaya, J. Ohata, M. K. Miller, A. E. Mangubat-Medina, M. J. Swierczynski, D. C. Yang, R. M. Rosenthal, B. V. Popp and Z. T. Ball, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C9CC00159J

Search articles by author

Spotlight

Advertisements