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

Pseudaminic 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.

Name thesis:degree_name

Master of Science (MSc)

Discipline thesis:degree_discipline

Chemistry

Grantor dc:publisher.institution

Science

Year dc:date.issued

2019

Author dc:creator

• Sequeira, Carita-Louise Aurelle

Advisors dc:contributor.advisor

• Ling, Changchun
• Sutherland, Todd C.

Committee members dc:contributor.committeemember

• Derksen, Darren J.
• Back, Thomas George
• Roesler, Roland

• pseudaminic acid
• synthesis

Statement dc:rights

• University 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.

Language dc:language.iso

eng

DOI

http://dx.doi.org/10.11575/PRISM/37362

OAI identifier oai:identifier

oai:ucalgary.scholaris.ca:1880/111370