Enantiomeric Excess Determination of Primary Amines

Abstract

Certain organic compounds can exist in two variations, known as enantiomers. Such compounds are characterized as being “chiral”. Enantiomers can exist in either R or S configurations, and the relative proportions of one configuration to another can be expressed in terms of something known as enantiomeric excess. When analyzing a particular sample of a compound, determination of the enantiomeric excess is important because enantiomers can display different effects biologically. For example, sometimes an enantiomer can have harmful effects while the other enantiomer has beneficial effects. The types of compounds we are focusing on in this project are known as primary amines. Primary amines play a critical role in various drugs, such as in L-Dopa that is commonly used in the treatment of Parkinson’s disease. This project sought to develop a method of determining the enantiomeric excess of chiral primary amines. This was to be accomplished by treating the amine with a specific reagent and then analyzing the product of that reaction by means of a technique known as NMR. Synthesis of the reagent has been successful and this reagent was treated with a primary amine to test if it had the ability to determine the enantiomeric excess of the amine.