Gamma-amino Acids and Gamma-peptide Foldamers

University Of Wisconsin-Madison, Madison WI

Investigators

Abstract

The Organic and Macromolecular Chemistry Program in the Chemistry Division at the National Science Foundation supports Professor Samuel Gellman at the University of Wisconsin, who will synthesize new, conformationally constrained -amino acids and derivatives, and evaluate the conformation of oligomers that contain these new subunits. The present focus of this research involves basic synthetic and structural chemistry. Specific goals of the proposed research are to develop efficient synthetic routes to new conformationally constrained peptide building blocks and to study the conformational behavior of oligomers that contain constrained residues with the aim of identifying new and stable foldamer secondary structures. Interest in the development of synthetic foldamers has been kindled by recognition of the many important and complex functions carried out by precisely folded oligomers, especially proteins, in biological systems. The proposed activities will expand the scope of previous landmark studies by pursuing an emerging family of foldamer compounds, the gamma peptides and their hybrids. Detailed understanding and research in synthetic foldamers will not only help to understand how biofoldamers fold and function but also enable the design of new materials with useful properties. The proposed foldamer research represents an excellent way to train young scholars for independent careers. Progress in this area demands applying a non-traditional combination of tools and concepts to areas as diverse as asymmetric organic synthesis and biophysical characterization of higher order molecular structure. Students who participate in this research, at the graduate or undergraduate levels, will emerge well-equipped to confront challenges in their independent careers. In addition, the proposed research offers an excellent basis for conveying to undergraduates in the classroom the essence, appeal, and significance of modern chemistry research. Specifically, this topic enables a lecturer to show how classical topics in organic reactivity and synthesis can be used to address new research challenges.