RUI: Synthesis of N-Alkyl Pyridones: Mechanism, Methodology and Application to Organic Materials

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This award is funded under the American Recovery and Reinvestment Act of 2009 (Public Law 111-5). This project will focus on the development of methods for the formation of N-alkyl pyridone containing structures, including amino acid homologues. N-Alkyl pyridones are interesting motifs due to their prevalence in natural products as well as their ability to serve as biological mimics in pharmaceutical targets. Recent disclosure of a lithium iodide promoted alkyl migration for the synthesis of N-alkyl pyridones has appeared and will be studied further. The synthesis of beta- and gamma-amino acids containing an N-alkyl pyridone moiety will also be pursued. Incorporation of such amino acids into peptides is expected to provide protein mimics with unique folding tendencies for application to both medicinal and material applications.With this award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Carolyn Anderson of the Department of Chemistry and Biochemistry at Calvin College. Professor Anderson's research efforts revolve around the development of facile methods for the synthesis and application of structures containing N-alkyl pyridones. Such chemistry will contribute a unique class of amino acid homologues, which will subsequently be used to expand our understanding of the helical structure of peptides containing these subunits. Successful development of this methodology will have an impact on the synthetic community as well as those involved in the development of organic materials and medicinal targets.