Palladium–Protein Oxidative Addition Complexes by Amine-Selective Acylation
Name
nihms-1687538.pdf
Description
Accepted version
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1.55 MB
Format
Unknown
Checksum (MD5)
e77c80e6086fe0c575ecbf5b9026872a
Author(s)
Dhanjee, Heemal H.
Buslov, Ivan
Windsor, Ian W.
Raines, Ronald T.
Pentelute, Bradley L.
Buchwald, Stephen L.
Date Issued
December 2020
Journal
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
Abstract
© 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike
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DOI of Published Version
https://doi.org/10.1021/jacs.0c09180
