ERA

Download the full-sized PDF of Synthesis of Lipooligosaccharide Antigens from MycobacteriaDownload the full-sized PDF

Analytics

Share

Permanent link (DOI): https://doi.org/10.7939/R3Q23R986

Download

Export to: EndNote  |  Zotero  |  Mendeley

Communities

This file is in the following communities:

Graduate Studies and Research, Faculty of

Collections

This file is in the following collections:

Theses and Dissertations

Synthesis of Lipooligosaccharide Antigens from Mycobacteria Open Access

Descriptions

Other title
Subject/Keyword
lipooligosaccharide
Mycobacteria
3,6-dideoxy
xylose
trehalose
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Bai, Bing
Supervisor and department
Lowary, Todd L. (Chemistry)
Examining committee member and department
Rivard, Eric (Chemistry)
Clive, Derrick L. J. (Chemistry)
West, Frederick G. (Chemistry)
Rempel, Brian (Chemistry, Augustana Campus)
Turnbull, Bruce (School of Chemistry, University of Leeds)
Department
Department of Chemistry
Specialization

Date accepted
2014-10-02T14:12:30Z
Graduation date
2014-11
Degree
Doctor of Philosophy
Degree level
Doctoral
Abstract
Lipooligosaccharides (LOSs) are one of the three major classes of glycolipids produced by mycobacteria. Over 15 LOSs have been isolated and characterized in the past three decades. However, there are only a small number of studies that have focused on the synthesis of LOSs molecules. In this thesis, I have developed a synthetic route to oligosaccharide fragments of LOS III from Mycobacterium gastri. To achieve our purpose, eight different building blocks were designed and synthesized. The L-xylopyranosides were prepared via stannanylidene acetal, a key intermediate for the selective protection of the hydroxyl groups. Two synthesized D-glucopyranosides were then coupled into an α,α-trehalose in 49% yield, while the coupling between the 3,6-dideoxy sugar alkene and terminal olefin failed to give any desired product. In the synthesis of the oligosaccharide target, a key intermediate pentasaccharide was prepared using a 2+1+2 strategy. Upon obtaining this pentasaccharide, two oligosaccharides, a nonasaccharide and an ocatasaccharide, were synthesized as key advanced intermediates to the LOS target.
Language
English
DOI
doi:10.7939/R3Q23R986
Rights
This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for the purpose of private, scholarly or scientific research. This thesis, or any portion thereof, may not otherwise be copied or reproduced without the written consent of the copyright owner, except to the extent permitted by Canadian copyright law.
Citation for previous publication

File Details

Date Uploaded
Date Modified
2014-10-06T15:47:48.953+00:00
Audit Status
Audits have not yet been run on this file.
Characterization
File format: pdf (PDF/A)
Mime type: application/pdf
File size: 4569144
Last modified: 2016:11:16 16:10:33-07:00
Filename: Bai_Bing_201409_PhD.pdf
Original checksum: 788e9f84e36e75247fb7c2da0ee79d3f
Activity of users you follow
User Activity Date