Description of Research with Mark Pugh
(In conjunction with Kerensa Sorensen-Stowell and Susan Ward)
I was formally trained to be a physical organic chemist, which means that I am trained to study stability, bond energy, enthalpies, entropies, etc. for organic molecules in relation to their modes or mechanism of action. The research I will be doing will be in conjunction with Sister Kerensa Sorensen-Stowell and Sister Susan Ward. Each semester one of us will be the principle investigator in charge of directing the organic research group.
I will likely accommodate 1-9 students the semester that I am the principle investigator on this combined research effort with Kerensa Sorensen-Stowell and Susan Ward. I will be in charge of these research projects Spring Semester 2017. If you are interested in doing research with me or with Sister Sorensen-Stowell or Sister Ward, come and talk to one of us.
Project #1: Isolation of a Furanocoumarin: Xanthotoxin from the Umbelliferae plant (aka Bishop's Flower). This research project was started by Dr. Pugh in an effort to isolate xanthotoxin from its natural source, Bishop's Flower. The molecule was used by ancient Egyptians to treat Leukoderma and other skin rashes. The individual that was to use this drug bathed in a bath of ground up Bishop's Flower. They would then lie out in the sun to treat their skin ailments. Today, xanthotoxin is widely used to treat T-cell lymphoma via extracorporeal photopheresis. The goal of the research project this fall is to increase isolated yields of xanthotoxin by the method of ultrasonification.
Projects #2 and #3: Formation of Imine Derivatives of Cinnamaldehyde. The key step in vision is the binding of retinol (vitamin A) to the enzyme opsin via a primary amine to form rhodopsin, an imine. When rhodopsin absorbs a photon of visible light, a cis double bond undergoes photochemical isomerization to trans. This change results in a nerve impulse that the brain interprets as a visual image. In an effort to mimic this process, we will be using the cis and trans versions of another conjugated aldehyde called cinnamaldehyde. We will then bind different primary amines, some alkyl and others aryl, to cinnamaldehyde via an imine bond. Currently we are binding aniline and cyclohexylamine to cinnamaldehyde. We will obtain colored and colorless products that are similar to rhodopsin. We will analyze these products via melting point, infrared spectroscopy, 1H NMR, 13C NMR, GC-MS, and UV-Vis spectroscopy.
Projects #4 and #5: Study of Stereoselective and Regioselective Reactions of the Bicyclic Alkene Nopol. These two projects are designed to study Markovnikov additions to a trisubstituted alkene, nopol. Because nopol is trisubstituted at the alkene, many addition reactions can be studied that are regiospecific. Nopol is also a sterically hindered bicyclic alkene, and will likely also result in stereospecific additions. Currently, we are investigating the formation of a halohydrin from the alkene nopol with NBS (N-bromosuccinimide) and water. Halohydrin reactions are both regiospecific and stereospecific (anti addition along double bond). We are also investigating the formation of an alcohol from the alkene nopol with mercuric acetate in tetrahydrofuran followed by reduction with basic sodium borohydride. This reaction known to be regiospecific and we hope due to the nature of nopol, stereospecific as well. We will analyze these products via melting point, infrared spectroscopy, 1H NMR, 13C NMR, and GC-MS.