Pentelute Lab MIT | Palladium-Mediated Arylation of Lysine in Unprotected Peptides
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.
Pentelute Lab, MIT, Cambridge, Chemistry, Molecular biology, technology development, peptide, protein-based therapeutics, chemical Biology, Bradley Pentelute
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Palladium-Mediated Arylation of Lysine in Unprotected Peptides

Palladium-Mediated Arylation of Lysine in Unprotected Peptides

DOI: 10.1002/anie.201611202 Published: 16 Feb 2017 Authors: Dr. Hong Geun Lee, Dr. Guillaume Lautrette, Prof. Bradley L. Pentelute, Prof. Stephen L. Buchwald

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.

Category
2017, Publications