Synthesis of a Vicinal Tricarbonyl Amide Derivative of L-Phenylalanine

摘要

Unnatural amino acids have found wide utility for the modification of the physical properties and biological activities of peptides, peptide mimetics, and, more recently, proteins. Due to their expanding utility, synthetic routes to novel unnatural amino acids, particularly those with unusual chemical properties, broaden the scope of what can be done in this area. Wasserman and co-workers have made significant contributions to the synthesis, structural characterization, and synthetic utility of the highly electrophilic vicinal 1,2,3-tricarbonyl moiety. They have also utilized its reactivity to develop inhibitors of serine proteases by replacing the terminal carboxyl group in peptides with the vicinal tricarbonyl moiety so that the nucleophilic serine in the active site could form a covalent bond with the central carbonyl carbon.