Our objective is to develop a simple, inexpensive model to better understand the biologically relevant reactions of halogenated hydrocarbons and characterize them by NMR spectroscopy. We currently have a model that mimics the adduct created by the reaction of ethylene dibromide (a known toxin and carcinogen) with cysteine and guanosine 5’-monophosphate. Early attempts led to side products including ethylene oxide and ethylene glycol; however, our most promising method to date reacts cysteine with 2-bromoethanol in sodium methoxide/methanol followed by reaction of the 2-hydroxyethyl adduct with HCl and later with guanosine 5’-monophosphate. By reacting other halogenated hydrocarbons through the same method, we can directly compare their unknown reactivity to the known toxicity of ethylene dibromide. If the adducts are similar, additional research on these chemicals can be conducted and if determined toxic, classify them in a means that prevents their use. However through this method, reactions with 3-bromopropanol and 70% 1-bromo-2-propanol/ 30% 2-bromo-1-propanol have failed to convert from their hydroxypropyl adduct to their hydrochloropropyl adduct, indicating the model needs additional research and development.
Advisor(s) or Committee Chair
Dr. Kevin Williams
Morgan, Brittany S., "Reaction of Halogenated Hydrocarbons with Cysteine and Nucleotides" (2012). Mahurin Honors College Capstone Experience/Thesis Projects. Paper 384.