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Ultra-rapid Electrophilic Cysteine Arylation

Year: 2023
Type: article
Abstract: Rapid bond-forming reactions are crucial for efficient bioconjugation. We describe a simple and practical strategy for facilitating ultra-rapid electrophilic cysteine arylation. Using a variety of sulfone-activated pyridinium salts, this uncatalyzed reaction proceeds with exceptionally high rate constants, ranging from 9800 to 320,000 M –1 ·s –1, in pH 7.0 aqueous buffer at 25 °C. Such reactions allow for stoichiometric bioconjugation of micromolar cysteine within minutes or even seconds. Even though the arylation is extremely fast, the chemistry exhibits excellent selectivity, thus furnishing functionalized peptides and proteins with both high conversion and purity.
DOI: 10.1021/jacs.3c10334
Authors: Bradley M. Lipka, Daniel S. Honeycutt, Gregory M. Bassett, Taylor N. Kowal, Max Adamczyk, Zachary C. Cartnick, Vincent M. Betti, Jacob M. Goldberg, Fang Wang
Language: English
Field: Chemistry
Open Access status: green
Funders: National Science Foundation, University of Connecticut, University of Rhode Island, National Institutes of Health, National Institute of General Medical Sciences, Division of Chemistry
OpenAlex ID: W4387770148
FWCI: 4.189
Cites: 52
Cited by: 41
Related to: 10