Palladium–Protein Oxidative Addition Complexes by Amine-Selective Acylation
Author(s)
Dhanjee, Heemal H.; Buslov, Ivan; Windsor, Ian W.; Raines, Ronald T.; Pentelute, Bradley L.; Buchwald, Stephen L.; ... Show more Show less
DownloadAccepted version (1.545Mb)
Open Access Policy
Open Access Policy
Creative Commons Attribution-Noncommercial-Share Alike
Terms of use
Metadata
Show full item recordAbstract
© Palladium oxidative addition complexes (OACs) are traditionally accessed by treating an aryl halide-containing substrate with a palladium(0) source. Here, a new strategy to selectively prepare stable OACs from amino groups on native proteins is presented. The approach relies on an amine-selective acylation reaction that occurs without modification of a preformed palladium(II)-aryl group. Once transferred onto a protein substrate, the palladium(II)-aryl group facilitates conjugation by undergoing reaction with a second, cysteine-containing protein. This operationally simple method is applicable to native, nonengineered enzymes as well as antibodies and is carried out in an aqueous setting and open to air. The resulting Pd-protein OACs are stable, storable reagents that retain biological activity and can be used to achieve protein-protein cross-coupling at nanomolar concentrations within hours.
Date issued
2020-12Department
Massachusetts Institute of Technology. Department of ChemistryJournal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Dhanjee, Heemal H, Buslov, Ivan, Windsor, Ian W, Raines, Ronald T, Pentelute, Bradley L et al. 2020. "Palladium–Protein Oxidative Addition Complexes by Amine-Selective Acylation." Journal of the American Chemical Society, 142 (51).
Version: Author's final manuscript
ISSN
0002-7863
1520-5126