The syntheses of new classes of oligocarbamates with differing substitution patterns towards the identification of novel folding patterns are proposed, which should ultimately lead to rational control of biological activity. A flexible synthetic route to oligocarbamates using the asymmetric reactions of epoxides to generate monomers and solid phase techniques to form oligomers is proposed. Helical structure can be verified experimentally (using a combination of NOESY NMR structural data and restrained molecular dynamics calculations) important questions regarding the relationship between monomer structure and oligomer secondary structure will be addressed. Finally, the biological activity of folded oligocarbates will be investigated. In particular, the synthesis of a potential anti-bacterial agent and students into the membrane permeability using this class of unnatural oligomer are proposed.
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| Peelen, Timothy J; Chi, Yonggui; Gellman, Samuel H (2005) Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate. J Am Chem Soc 127:11598-9 |
| Peelen, Timothy J; Chi, Yonggui; English, Emily Payne et al. (2004) Synthesis of 4,4-disubstituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into 12-helical beta-peptides. Org Lett 6:4411-4 |
