Work

Palladium‐Mediated Arylation of Lysine in Unprotected Peptides

Year: 2017

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201611202

Authors: Hong Geun Lee, Guillaume Lautrette, Bradley L. Pentelute, Stephen L. Buchwald

Institution: Massachusetts Institute of Technology

Language: English

Topic: Catalytic Cross-Coupling Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Institutes of Health, National Institute of General Medical Sciences

Award: Cysteine Arylation