Doctor of Philosophy (PhD)
Useful mechanistic studies to date concerning sugar detection by arylboronic acid chemosensors have mainly involved the elucidation of equilibrium constants and the role of boron-nitrogen interactions in signal transduction. However, several discreet sugarboronate complexes exist in solution. This is due to the complex equilibria between isomeric species of even the simplest monosaccharides. Relatively few reports have been devoted to a systematic study of the structures of each of the corresponding individual sugar-boronate complexes. We have investigated some of the precise regio- and stereochemical features of the various equilibrating sugar isomers that induce selective signal transduction. As a result of this study, one may be better able to predict selective spectrophotometric responses of a monosaccharide in a natural matrix. Additionally, our findings are potentially applicable to selective analyses of more complex compounds via their terminal sugar residue structures. Additionally, during the course of this work, a unique example of a chemosensor (3.1) that is selective for ribose, adenosine, nucleotides, nucleosides and congeners was discovered. The combined use of chemosensors exhibiting complementary reactivities was shown to obtain enhanced selectivity for ribose and rare saccharides. A structurally-related xanthene chemosensor (4.6) that is selective for the sulfur-containing amino acids cysteine and homocysteine is also described herein.
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Jiang, Shan, "Stereochemical and Regiochemical Trends in the Selective Spectrophotometric Detection of Biological Molecules" (2007). LSU Doctoral Dissertations. 2088.