The Development of Di-N-Acetyl-L-Pyranosides for the Synthesis of Pseudaminic Acid and 8-epi-Legionaminic Acid

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dc.contributor.advisorLing, Changchun
dc.contributor.advisorSutherland, Todd C.
dc.contributor.authorSequeira, Carita-Louise Aurelle
dc.contributor.committeememberDerksen, Darren J.
dc.contributor.committeememberBack, Thomas George
dc.contributor.committeememberRoesler, Roland
dc.date2020-02
dc.date.accessioned2019-12-20T22:39:26Z
dc.date.available2019-12-20T22:39:26Z
dc.date.issued2019-12-19
dc.description.abstractPseudaminic acid, Legionaminic acid, and epimers are key bacterial nonulosonic acids found in the flagella of pathogenic bacteria. These sugars are found to be crucial to flagellar assembly and are thus attractive targets for raising an immune response against. By retrosynthetic analysis, we hypothesized that using L-sugars as starting materials for synthesis of the key hexose intermediates was a novel and practical route. The primary goal of the thesis was to develop a synthetic methodology that was adaptable to synthesizing both di-2,4-N-acetyl-2,4,6-trideoxy-altropyranoside and di-2,4-N-acetyl-2,4,6-trideoxy-Lgulopyranoside: the key intermediates in the biosynthetic pathways of Pseudaminic acid and 8-epiLegionaminic acid from L-fucose and L-rhamnose respectively. Chapter 1 gives a brief introduction to immunity and bacterial nonulosonic acids; particularly, Pseudaminic acid and 8-epi-Legionaminic acid. The biosynthetic pathways of Pseudaminic acid and Legionaminic acid are also summarized. Chapter 2 provides detailed reviews on the chemical methodologies reported in the literature for the synthesis of Pseudaminic acid and 8-epi-Legionaminic acid. Chapter 3 contains the bulk of the work of this thesis toward the development of a new methodology toward the synthesis of the key hexoses di-2,4-N-acetyl-2,4,6-trideoxy-altropyranoside and di-2,4-Nacetyl-2,4,6-trideoxy-L-gulopyranoside. Chapter 4 details the experimental procedures and spectroscopic data of all synthesized compounds given in Chapter 3.en_US
dc.identifier.citationSequeira, C.-L. A. (2019). The Development of Di-N-Acetyl-L-Pyranosides for the Synthesis of Pseudaminic Acid and 8-epi-Legionaminic Acid (Master's thesis, University of Calgary, Calgary, Canada). Retrieved from https://prism.ucalgary.ca.en_US
dc.identifier.doihttp://dx.doi.org/10.11575/PRISM/37362
dc.identifier.urihttp://hdl.handle.net/1880/111370
dc.language.isoengen_US
dc.publisher.facultyScienceen_US
dc.publisher.institutionUniversity of Calgaryen
dc.rightsUniversity of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.en_US
dc.subjectpseudaminic aciden_US
dc.subjectsynthesisen_US
dc.subject.classificationImmunologyen_US
dc.subject.classificationChemistry--Organicen_US
dc.titleThe Development of Di-N-Acetyl-L-Pyranosides for the Synthesis of Pseudaminic Acid and 8-epi-Legionaminic Aciden_US
dc.typemaster thesisen_US
thesis.degree.disciplineChemistryen_US
thesis.degree.grantorUniversity of Calgaryen_US
thesis.degree.nameMaster of Science (MSc)en_US
ucalgary.item.requestcopytrueen_US
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