Details

Autor(en) / Beteiligte

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

Titel

Rapid nickel(ii)-promoted cysteine S-arylation with arylboronic acidsElectronic supplementary information (ESI) available: Complete characterization and experimental procedures. See DOI: 10.1039/c9cc00159j

Erscheinungsjahr

2019-02

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• 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. Nickel salts catalyze fast cysteine arylation with 2-nitroarylboronic acids. The process uses cheap, readily-available reagents and allows introduction of diverse chemical handles.