Palladium-Mediated Arylation of Lysine in Unprotected Peptides
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Author(s)
Lee, Hong Geun
Lautrette, Guillaume
Pentelute, Bradley L.
Buchwald, Stephen Leffler
Date Issued
February 2017
Journal
Angewandte Chemie International Edition
Publisher
Wiley-Blackwell
Citation
Lee, Hong Geun et al. “Palladium-Mediated Arylation of Lysine in Unprotected Peptides.” Angewandte Chemie International Edition 56, 12 (February 2017): 3177–3181 © 2017 Wiley-VCH Verlag GmbH & Co
Version
Author's final manuscript
Abstract
A mild method for the arylation of lysine in an unprotected peptide is presented. In the presence of a preformed biarylphosphine-supported palladium(II)–aryl complex and a weak base, lysine amino groups underwent C−N bond formation at room temperature. The process generally exhibited high selectivity for lysine over other amino acids containing nucleophilic side chains and was applicable to the conjugation of a variety of organic compounds, including complex drug molecules, with an array of peptides. Finally, this method was also successfully applied to the formation of cyclic peptides by macrocyclization.
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/10.1002/ANIE.201611202
