Folded peptides for asymmetric catalysis: Structures and functions

ORGN 348

Scott J. Miller, scott.miller@yale.edu, Department of Chemistry, Yale University, 225 Prospect Street, P. O. Box 208107, New Haven, CT 06520-8107
Modern organic synthesis depends heavily on the use of catalysts for selective transformations. We have discovered a class of synthetic peptides that catalyze a number of enantioselective and regioselective reactions. This presentation will describe the discovery and use of peptides containing proteinogenic and non-natural amino acids for a variety of asymmetric bond formations. The connections between peptide sequence and stereoselectivity will be explored in a range of mechanistically distinct reactions. Prospects for generalizations and eventual design of catalysts from first principles will be evaluated. Likewise, their application to the selective modification of complex molecules, including biologically active natural products, will be described.