Cyclic aromatic donor-acceptor foldmers with a hairpin turn

ORGN 188

Chelsea R. Martinez, seachel@mail.utexas.edu, Department of Chemistry and Biochemistry, University of Texas at Austin, 1 University Station A5300, Austin, TX 78712 and Brent L. Iverson, Department of Chemistry and Biochemistry, The University of Texas at Austin, 1 University Station, A5300, Austin, TX 78712.
We have employed aromatic donor-acceptor interactions between the electron-rich 1,5-dialkoxy-naphthalene (Dan) and electron-poor 1,4,5,8-naphthalene-tetracarboxylic diimide (Ndi) modular units in the past to program both inter- and intramolecular folding and assembly. Solid-phase peptide synthetic methods in concert with native chemical ligation were used to constrain non-alternating sequences of Dan and Ndi into cyclic molecules intended to adopt a hairpin-like folding topology. For example, a trimer of linked Dan-Dan-Ndi units was synthesized and cyclized such that the Ndi intercalates between Dan units in the cyclic structure. We are currently characterizing the structures and properties of the molecules.
 

Total Synthesis, Materials, Devices and Switches, Molecular Recognition and Self-Assembly, Biologically-Related Molecules and Processes
8:00 PM-10:00 PM, Sunday, August 19, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007