ORGN 443 |
Progress in the development of a molecular building block approach toward nanoscale scaffolds
| Christopher G. Levins and Christian E. Schafmeister. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260 |
| We are developing methodology for the modular synthesis of nanoscale molecular scaffolds with designable three dimensional shapes. These scaffolds are assembled on solid support from orthogonally protected bis-amino acids in two steps: amide bonds are formed between each monomer using the standard Fmoc peptide synthesis techniques; the flexible scaffolds are conformationally rigidified through the formation of diketopiperazine rings between neighboring monomers. Currently, we are investigating the rigidity of the scaffold structure using fluorescence resonance energy transfer (FRET). Toward this end, four scaffolds, each with a different sequence of 4-hydroxyproline monomer stereoisomers, were synthesized, and the termini were functionalized with napthyl (donor) and dansyl (acceptor) groups. The structure and conformation of these scaffolds is being determined by 2D-NMR, and will be compared to predictions based upon molecular mechanics calculations. 
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Total Synthesis, Process R&D, Combinatorial, Bioorganic, Physical Organic Chemistry
8:00 PM-10:00 PM, Tuesday, August 24, 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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