Molecular Architectures and Assemblies from Natural and Unnatural Amino Acids
James S. Nowick Department of Chemistry University of California, Irvine

Abstract: This talk will describe my program of research involving the design, synthesis, and structural evaluation of molecules that are inspired by proteins. My students and I are developing unnatural building blocks that can be used alone or combined with natural amino acids to make synthetic molecules that mimic some of the structures and interactions of proteins.

The first half of the talk will focus on the development of molecules that mimic the folding and interaction of protein β-sheets. β-Sheets are nearly ubiquitous features of proteins that consist of extended peptide strands that held together in part by a network of hydrogen bonds. A particularly exciting and important feature of β-sheets is their ability to interact by means of the unsatisfied hydrogen-bonding valences along their edges. Interactions between the edges of β-sheets occur widely in proteins and are involved in both normal protein function and in diseases ranging from cancer and AIDs to Alzheimer's and Huntington's disease. Our research group has developed unnatural amino acids such as "Hao" that induce mimic the hydrogen-bonding properties of β-sheets and induce β-sheet structure and interactions when incorporated into peptides. By studying the structure and interactions of peptides containing unnatural amino acids such as "Hao", we hope to gain insight into β-sheet interactions between proteins and develop new treatments for diseases. Some of these studies will be described.

The second half of the talk will focus on the development of nanometer-scale amino acids for biomolecular nanotechnology. Proteins get their remarkable properties as receptors, catalysts, and effectors of biological processes in part because their relatively large size (nanometers, rather than angstroms) allows them to grip and engulf other molecules. Dozens or hundreds of naturally occurring α-amino acids are required to make up a protein, and it is not generally possible to design functional proteins from scratch in part because of their relatively complexity. With the goal of creating molecules that mimic some of the structures and functions of proteins, our group has developed the giant amino acid building blocks "Adc" and "Abc" as building blocks for the creation of nanometer-scale structures that are designed to mimic and interact with proteins and other biomacromolecules. Studies of water-soluble nanorods of up to 10 nm in length, nanometer-scale macrocyclic receptors, and other giant peptides will be described.


"What I Have Learned by Using Chemical Model Systems to Study Biomolecular Structure and Interactions" Nowick, J. S. Org. Biomol. Chem. 2006, 4, 3869-3885.

"Nanometer-Scale Amino Acids for Biomolecular Nanotechnology" Nowick, J. S.; Gothard, C. M.; Kang, S.-W.; Maitra, S. In Understanding Biology Using Peptides, Proceedings of the 19th American Peptide Symposium; Blondelle, S. E.; Ed.; Springer: New York, NY, 2006; pp. 673-674.

"Enantioselective Molecular Recognition between β-Sheets" Chung, D. M.; Nowick, J. S. J. Am. Chem. Soc. 2004, 126, 3062-3063. "Sequence-Selective Molecular Recognition Between β-Sheets", Nowick, J. S.; Chung, D. M. Angew. Chem., Int. Ed. 2003, 42, 1765-1768.

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