(Georgia Institute of Technology, 2021-08-19)
Mckenna, Kristin Ruth
The origin and prebiotic functions of carbohydrates are not well characterized. Limitations in analytical methodology to analyze the regio- and stereochemistry of carbohydrates in complex mixtures exacerbates this problem. Several ion mobility-tandem mass spectrometry techniques were developed to study model prebiotic carbohydrate reactions. Covalent derivatization with 3-carboxy-5-nitrophenylboronic acid (3C5NBA) was determined to improve these characterizations and allow for more complete structural analysis by tandem mass spectrometry. Cyclic ion mobility spectrometry improved the ability to distinguish four monosaccharide and eight disaccharide isomers as their 3C5NBA derivatives. Organic acids were also analyzed for their potential to improve carbohydrate separations as noncovalent modifiers. The optimal organic acid modifiers were determined to be L-malic acid and N-methyl-D-aspartic acid, which were further characterized through a more sensitive, Fourier transform-based ion mobility method.