A dynamic combinatorial library of histidine-based pseudopeptide oligomers templated against transition metal ions

ORGN 700

Masaomi Matsumoto, Masaomi.matsumoto-1@ou.edu, Department of Chemistry and Biochemistry, The University of Oklahoma, 620 Parrington Oval, Norman, OK 73069 and Kenneth M. Nicholas, knicholas@ou.edu, Chemistry and Biochemistry, University of Oklahoma, 620 Parrington Oval, Norman, OK 73019.
Our long term goal is to develop dynamic combinatorial chemistry for constructing metalloenzyme mimics by templating a Dynamic Combinatorial Library (DCL) against a transition metal ion and a transition state mimic. In a DCL, reversible reactions are used to create a distribution of products under thermodynamic control. By applying conditions (such as a template) to thermodynamically favor one product, we can shift the equilibrium toward the "best binder". We have developed a DCL based on acid-catalyzed hydrazone exchange using α-N-(3-dimethoxymethylbenzoyl)L-histidine hydrazide (1) as the monomer. Under acidic conditions, 1 forms a small distribution of cyclic oligomers. Templating experiments using zinc and copper ion are ongoing. Progress in the development of this metal-templated DCL will be discussed.

 

Asymmetric Reactions, Molecular Recognition, Self Assembly, Bioorganic Chemistry, Process R&D
8:00 PM-10:00 PM, Wednesday, 16 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005