A synthetic approach to water soluble nanoscale molecules with controlled structures

ORGN 735

Christian E. Schafmeister, Stephen A. Habay, Christopher G. Levins, Paul M. Morgan, and Gregory H. Bird. Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260
We have developed a general approach to the design and synthesis of functionalized macromolecules with predictable three-dimensional structures. Our approach involves the synthesis of stereochemically pure cyclic bis-amino acid monomers that are coupled through pairs of amide bonds to create spiro-linked oligomers of specific constitution. The oligomers are efficiently assembled on solid support using peptide synthesis techniques to first create a flexible oligomer that is then rigidified by the simultaneous formation of a second set of amide bonds between each adjacent pair of monomers. The structure of the resulting spiro-linked oligomers is controlled by the sequence and stereochemistry of the component monomers. Most of the oligomers that we have synthesized are soluble in aqueous solution, making them compatible with bioactivity studies. Potential uses for these molecules are in drug design and in the construction of nanoscale molecular devices. This presentation will describe the synthesis of several monomers, their assembly into functionalized spiro-linked oligomers and their structural characterization.

 

Proteins, Peptides, and Amino Acids
8:00 AM-12:00 PM, Thursday, August 26, 2004 Pennsylvania Convention Center -- 201A, Oral

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004