NSF Award
1900483
With this Award, the Chemical Synthesis Program of the NSF Division of Chemistry is supporting the research of Professor Jeffrey Cannon at Occidental College who works with undergraduate researchers to synthesize unnatural amino acids. Amino acids are one of the fundamental building-blocks of biological systems. Professor Cannon and his research team are devising new strategies for the synthesis of these building blocks that can provide useful quantities of amino acids that are not readily isolated from natural sources. Furthermore, because their three-dimensional shape or stereochemistry is critical for proper function, this research is working to control the exact arrangement of atoms in the amino acid products so that the products function properly in biological systems. Professor Cannon and his research team then apply these results to the chemical synthesis of a family of molecules known as indolizidines. The indolizidine structure is found in many biologically-active molecules. Molecules of this type have many applications as pharmaceuticals and other biological agents. The broader impacts include new syntheses and applications of unnatural amino acids as well as the development of biologically-active nitrogen-containing molecules. This project also creates summer research fellowships for undergraduates in synthetic chemistry with an emphasis on support for underrepresented students.<br/><br/>There are many limitations to the syntheses of unnatural amino acids, especially those that are fully-substituted. Professor Cannon and his students are developing the reactions of dianionic enolates to provide ready stereoselective access to unnatural amino acid derivatives and other synthetic precursors. His research group is investigating the use of a chiral auxiliary to direct the stereochemistry of reactions of dianionic enolates. These reactions are studied experimentally as well as computationally in order to understand the elements of control provided by these auxiliaries. The goal is to provide a robust and accessible system for the synthesis of amino acids. These reactions are tested in complex settings in order to understand their limitations and inspire further reaction development.<br/><br/>This award reflects NSF's statutory mission and has been deemed worthy of support through evaluation using the Foundation's intellectual merit and broader impacts review criteria.
