ORGN 635 |
| N-substituted glycine oligomers, or peptoids, are a promising class of peptidomimetics that have potential applications as new biological probes and therapeutics. Understanding how amide side chain composition affects peptoid secondary structure is an important goal, as structure often dictates biological function. Peptoids containing α-chiral amide side chains have been shown to adopt helical and threaded loop conformations. Here we present our efforts toward modulating the stability of the peptoid helix by the strategic introduction of electronically deactivated and/or sterically hindered amines. Specifically, we show methods to destabilize threaded loop secondary structures, resulting in helical conformations. These studies have prompted the synthesis of new, deactivated amine building blocks for peptoid synthesis. We have found microwave irradiation to be a convenient and effective heating method for installing these amines into peptoids. This poster will present our ongoing synthetic work and structural characterization studies in this area. |
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Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |