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

Kengo Hanaya, Jun Ohata, Mary K. Miller, Alicia E. Mangubat-Medina, Michael J. Swierczynski, David C. Yang, Reece M. Rosenthal, Brian V. Popp, Zachary T. Ball

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8 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2841-2844
Number of pages4
JournalChemical Communications
Volume55
Issue number19
DOIs
Publication statusPublished - 2019 Jan 1

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ASJC Scopus subject areas

  • Catalysis
  • Electronic, Optical and Magnetic Materials
  • Ceramics and Composites
  • Chemistry(all)
  • Surfaces, Coatings and Films
  • Metals and Alloys
  • Materials Chemistry

Cite this

Hanaya, K., Ohata, J., Miller, M. K., Mangubat-Medina, A. E., Swierczynski, M. J., Yang, D. C., Rosenthal, R. M., Popp, B. V., & Ball, Z. T. (2019). Rapid nickel(ii)-promoted cysteine: S -arylation with arylboronic acids. Chemical Communications, 55(19), 2841-2844. https://doi.org/10.1039/c9cc00159j