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Determining the Solution Conformational Entropy of Oligosaccharides

Title: Determining the Solution Conformational Entropy of Oligosaccharides: Isolating the Effects of Anomeric Configuration, Glycosidic Linkage, Degree of Polymerization, Linearity versus Cyclicity and Hydrogen Bonding.
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Name(s): Boone, Marcus Alexander, 1977-, author
Striegel, André M., professor directing dissertation
Collins, Emmanuel, outside committee member
Dorsey, John, committee member
Nymeyer, Hugh, committee member
Department of Chemistry and Biochemistry, degree granting department
Florida State University, degree granting institution
Type of Resource: text
Genre: Text
Issuance: monographic
Date Issued: 2009
Publisher: Florida State University
Place of Publication: Tallahassee, Florida
Physical Form: computer
online resource
Extent: 1 online resource
Language(s): English
Abstract/Description: Oligosaccharides have various fundamental roles, ranging from providing nutritional and flavoring support to being involved in fertilization and parasite infection processes. Maltooligosaccharides are used heavily in the food and pharmaceutical industries, cellooligosaccharides have shown promise as prebiotic candidates, and cyclodextrins are potential candidates for drug delivery. Factors such as degree of polymerization and hydrogen bonding play key roles in the aforementioned processes and phenomena. Other factors such as anomeric configuration have been shown to influence bacterial binding and docking, while the glycosidic linkage is known to be a factor in binding processes such as those related to the interspecies spreading of avian influenza virus. Our group has pioneered the use of size-exclusion chromatography (SEC) in investigating solution conformational entropy (∆S) of select O-linked disaccharides and their monosaccharide constituents. I recently expanded the scope of these investigations to quantitate the ∆S of several homologous series of oligosaccharides, malto- and cellooligosaccharides and cyclodextrins. By using SEC and appropriate selection of hydrogen-bond accepting or non hydrogen-bond accepting solvents, I was able to isolate and quantitate the individual contributions of degree of polymerization, anomeric configuration, linearity versus cyclicity, and hydrogen bonding to the solution conformational entropy of the oligosaccharides. Due to the importance of oligosaccharides in biomolecular recognition phenomena, the next step was to study oligosaccharides at quasi-physiological conditions, i.e., in an aqueous solvent, at 37° C, and at a pH of 7.39. In the final step of the research I isolated the effects of glycosidic linkage on solution conformational entropy. To this effect, I compared homologous series of α-(1→6) and β-(1→3) oligomers, individually, to their α-(1→ 4) and β-(1→4) counterparts, respectively. The α-(1→6) oligomers were the isomaltosides with DP 2-7, which were compared to the maltooligosaccharides. The β-(1→3) series examined were the laminarbiosides with DP 2-7, compared to the previously studied cellooligosaccharides.
Identifier: FSU_migr_etd-3533 (IID)
Submitted Note: A Dissertation submitted to the Department of Chemistry and Biochemistry in partial fulfillment of the requirements for the degree of Doctor of Philosophy.
Degree Awarded: Spring Semester, 2009.
Date of Defense: February 27, 2009.
Keywords: Size-exclusion Chromatography, Conformational Entropy, Oligosaccharides
Bibliography Note: Includes bibliographical references.
Advisory Committee: André M. Striegel, Professor Directing Dissertation; Emmanuel Collins, Outside Committee Member; John Dorsey, Committee Member; Hugh Nymeyer, Committee Member.
Subject(s): Biochemistry
Biophysics
Molecular biology
Persistent Link to This Record: http://purl.flvc.org/fsu/fd/FSU_migr_etd-3533
Owner Institution: FSU

Choose the citation style.
Boone, M. A. (2009). Determining the Solution Conformational Entropy of Oligosaccharides: Isolating the Effects of Anomeric Configuration, Glycosidic Linkage, Degree of Polymerization, Linearity versus Cyclicity and Hydrogen Bonding. Retrieved from http://purl.flvc.org/fsu/fd/FSU_migr_etd-3533