Bis-amino acids: A building block approach to macromolecules with tailored shapes and properties

ORGN 391

Christian E. Schafmeister, meister@pitt.edu, Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260
We have developed a synthetic methodology for synthesizing oligomers with complex and designed three-dimensional structures. Our approach involves the synthesis of stereochemically pure cyclic bis-amino acid molecular building blocks 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. In this presentation we will describe the synthesis and characterization of nanometer scale oligomers designed to have different linear and curved structures.