General Installation of (4H)-Imidazolone cis-Amide Bioisosteres Along the Peptide Backbone

• DOI: 10.1021/jacs.3c13825
• Publication Date: 2024-04-17T11:51:07Z
• Authors: Brendan J. Wall; Krishna K. Sharma; Emily A. O’Brien; Aaron Donovan; Brett VanVeller
• Keywords: Amidine; Amide; Chromophore; Peptide bond; Tandem; Peptide Synthesis; Cyclic peptide

Imidazolones represent an important class of heterocycles present in a wide range pharmaceuticals, metabolites, and bioactive natural products serve as the active chromophore green fluorescent protein. Recently, imidazolones have received attention for their ability to act nonaromatic amide bond bioisotere which improves pharmacological properties. Herein, we tandem amidine installation cyclization with adjacent ester yield (4