Expanding the scope of dynamic combinatorial chemistry: New building blocks for the development of novel receptors

ORGN 419

Lindsey A. Ingerman, ingerman@email.unc.edu, Department of Chemistry, University of North Carolina, CB 3290, Chapel Hill, NC 27599 and Marcey L. Waters, mlwaters@email.unc.edu, Department of Chemistry, University of North Carolina at Chapel Hill, CB 3290, Chapel HIll, NC 27599.
Dynamic combinatorial chemistry (DCC) is a promising new method for rapidly developing new receptors with high affinity and selectivity for their targets. However, to date the building blocks which have been used to generate dynamic combinatorial libraries (DCLs) have largely lacked structural complexity and diversity. We are interested in integrating new types of building blocks which will expand both the scope of DCC and generate potentially interesting new receptors. Firstly, to further investigate nucleotide recognition we have incorporated beta-hairpin peptides to mimic the binding interactions between proteins and nucleotides. We are using cysteine containing peptides in conjunction with aromatic dithiols to generate host macrocycles via disulfide exchange. Secondly, we are exploring the generation of “doubly dynamic” DCLs through hydrazone exchange and the use of novel diazobenzene containing monomers which can undergo facile isomerization, expanding the potential host systems that can be generated. Results will be presented.
 

Heterocycles and Aromatics, Molecular Recognition and Self Assembly
8:00 PM-10:00 PM, Tuesday, April 8, 2008 Morial Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008