Anion recognition and membrane transport using zinc (II)-coordinated tyrosine derivatives

ORGN 199

Edward J. O'Neil, eoneil@nd.edu, Hua Jiang, and Bradley D. Smith, smith.115@nd.edu. Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556
The construction of complicated multivalent molecular recognition systems requires the development of versatile building blocks that can be readily attached to organic scaffolds or incorporated into oligomers. Amino acid derivatives are attractive for the obvious reason that they can be incorporated into peptides. Here we report that tyrosine-derived Zn2+ coordination complexes and their fluorescent dye-conjugates can be synthesized in a short, high yielding procedure via Mannich reaction. The Zn2+ complexes are highly water-soluble but in the presence of lipophilic anions they readily transfer into vesicle membranes. Furthermore, they induce the translocation of anionic phospholipids. The facilitated transport of anions in and out of cells will also be presented.

 

Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006