Designed amino acids with an N-heterocyclic carbene sidechain

CHED 294

John P. Morgan, jmorgan@bloomu.edu, Heather Pursel, and Saad Amin. Department of Chemistry, Bloomsburg University of Pennsylvania, 400 East Second Street, Bloomsburg, PA 17815
In order to expand the scope of natural proteins, the synthesis of suitably protected designer amino acids incorporating N-heterocyclic carbenes (NHC's) is presented. These new amino acids are based on a phenylalanine framework which is modified by metal-catalyzed coupling chemistries or aromatic substitution reactions. The design of a NHC-containing amino acid is expected to expand the scope of unnatural amino acid suppression, leading to the incorporation of a very reactive sidechain for covalent modification of natural proteins. In addition, the high binding constants of NHC's for metal ions will allow the synthesis of metal-bound peptides for pharmaceutical purposes.