ORGN 199 |
Conformational switching in a new family of water-soluble peptoid oligomers
| Sung B. Y. Shin and Kent Kirshenbaum. Department of Chemistry, New York University, 100 Washington Square East, Room 1001, New York, NY 10003 |
| Oligo-N-substituted glycines, or peptoids, are an important class of sequence-specific “foldamers” capable of forming stable helical structures even at short chain lengths. Previous examples of folded peptoids have relied upon the incorporation of bulky hydrophobic sidechains to drive folding, complicating efforts to identify sequences capable of forming stable structures in aqueous conditions. Here we utilize L-phenylalanine tert-butyl ester as a low-cost submonomer reagent for the solid phase synthesis of a family of (S)-N-(1-carboxy-2-phenylethyl)-glycine oligomers. We demonstrate that these oligomers form stable helical structures in aqueous solution. Circular dichroism spectra indicate that the conformation is dramatically responsive to variations in pH and solvent composition. 
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Asymmetric Reactions and Syntheses, Metal-Mediated Reactions, Materials, Molecular Recognition
8:00 PM-10:00 PM, Sunday, August 22, 2004 Pennsylvania Convention Center -- Hall D, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- Hall D, Sci-Mix
Division of Organic Chemistry
The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004
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