Project 2 is devoted to the design and synthesis of libraries based on nature's building blocks. In one subproject, Professor Jeffrey Aubé of the KU Department of Medicinal Chemistry directs a program based on his group's continuing interest in peptide mimicry. The biological activity of a peptide often depends on its particular conformation or secondary structure, and so the design of small molecules that mimic specific conformations is one approach to biologically active molecules. The heterocyclic analog of the γ-turn structure shown is one example of this approach.
Professor Apurba Dutta, who also works in the KU Med Chem department, is interested in libraries based on library scaffolds. His group has worked out a number of straightforward, high-yielding methods to prepare carbohydrate-like structures that can be readily diversified using straightforward chemistry.
The example depicted below begins with the amino serine, which is straightforwardly converted into a furanose-inspired scaffold that contains multiple points for additional decoration.
