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Palladium‐Mediated Arylation of Lysine in Unprotected Peptides
Author(s) -
Lee Hong Geun,
Lautrette Guillaume,
Pentelute Bradley L.,
Buchwald Stephen L.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201611202
Subject(s) - palladium , lysine , chemistry , amino acid , peptide , cyclic peptide , molecule , aryl , side chain , nucleophile , peptide bond , selectivity , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , polymer , alkyl
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.