Identifier

etd-02152007-114707

Degree

Doctor of Philosophy (PhD)

Department

Chemistry

Document Type

Dissertation

Abstract

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.

Date

2007

Document Availability at the Time of Submission

Secure the entire work for patent and/or proprietary purposes for a period of one year. Student has submitted appropriate documentation which states: During this period the copyright owner also agrees not to exercise her/his ownership rights, including public use in works, without prior authorization from LSU. At the end of the one year period, either we or LSU may request an automatic extension for one additional year. At the end of the one year secure period (or its extension, if such is requested), the work will be released for access worldwide.

Committee Chair

Robert Strongin

Included in

Chemistry Commons

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