In this project, funded by the Chemical Structure, Dynamics, and Mechanisms-B Program of the Chemistry Division, Professor Babak Borhan of the Chemistry Department at Michigan State University (MSU) is developing new methods to identify the chirality of organic molecules. Chirality, also referred to as handedness, is an important property of molecules. Human hands are not identical, but mirror images of each other (the two hands are not superimposable). The relationship between two objects that are mirror images of each other, have a center of chirality, and are referred to as enantiomers. There are numerous examples of enantiomers in biology and medicine. For example, Thalidomide, a drug that was used in the late 1960s and early 1970s, led to the embryonic mis-development of a number of babies is an example of a mixture of enantiomers. One of the enantiomers was biologically active as an anti-nausea agent to treat morning sickness in pregnant women. The other enantiomer was teratogenic, which interfered with the correct embryonic development. The drug was given as a mixture of the two enantiomers, causing tragedy. From this experience, scientists have learned that the ability to identify the chirality of a molecule is of utmost importance. The Borhan group is developing new methods to rapidly identify the chirality of organic molecules to ensure the safety of drugs such as Thalidomide. Professor Borhan organizes and leads Project SEED activities at MSU. Project SEED is a ten-week summer program funded in part through the American Chemical Society and various organizations at MSU, to support the research of high school students from financially-disadvantaged families.
The goals of the project are to provide simple, rapid, efficient, and non-ambiguous procedures for the absolute stereochemical determination of chiral organic molecules, many of which are synthetic intermediates of bioactive compounds or newly isolated pharmacologically-active metabolites. The project relies heavily on Circular Dichroism (CD) as the tool for observing the host-guest interactions between the chiral compounds and the receptors. The functionalities of interest include chiral epoxides, phosphines, phosphine oxides, boranes, alkenes, alkynes, and alkyl arenes. In addition, the endowed helicity of the supramolecular complexes, induced through interactions with the bound asymmetric guest molecules, will be used towards asymmetric catalysis.
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.
