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Permanent link (DOI): https://doi.org/10.7939/R3BV7B405

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Synthesis of Furanose Sugar Nucleotides from Mycobacterium tuberculosis and Campylobacter jejuni Open Access

Descriptions

Other title
Subject/Keyword
Furanose sugar nucleotides
Campylobacter jejuni
Mycobacterium tuberculosis
Type of item
Thesis
Degree grantor
University of Alberta
Author or creator
Snitynsky, Ryan Blake
Supervisor and department
Lowary, Todd (Chemistry)
Examining committee member and department
Petersen, Nils (Chemistry)
Campbell, Robert (Chemistry)
Department
Department of Chemistry
Specialization

Date accepted
2014-04-02T10:58:19Z
Graduation date
2014-06
Degree
Master of Science
Degree level
Master's
Abstract
Five-membered ring furanose sugars, though absent in mammals, have been found in the cell walls of pathogenic bacteria such as Mycobacterium tuberculosis and Campylobacter jejuni. Because these sugars are only found in microorganisms, it has been proposed that inhibiting the enzymes these bacteria use to process furanose sugars could lead to the development of new targeted treatments against disease. To study these enzymes, access to their natural substrates and analogues is essential. In this work, we explored methods of producing these sugar nucleotides. First, activated donors were used to attempt to make a glycosyltransferase enzyme (GlfT2) work in reverse to produce sugar nucleotides. Subsequently, we attempted to expand the substrate scope of a nucleotidyltransferase (GalPUT). Finally, a wholly synthetic approach was developed to synthesize two nitrogen-containing furanose sugar nucleotides.
Language
English
DOI
doi:10.7939/R3BV7B405
Rights
Permission is hereby granted to the University of Alberta Libraries to reproduce single copies of this thesis and to lend or sell such copies for private, scholarly or scientific research purposes only. Where the thesis is converted to, or otherwise made available in digital form, the University of Alberta will advise potential users of the thesis of these terms. The author reserves all other publication and other rights in association with the copyright in the thesis and, except as herein before provided, neither the thesis nor any substantial portion thereof may be printed or otherwise reproduced in any material form whatsoever without the author's prior written permission.
Citation for previous publication
Snitynsky, R. B.; Lowary, T. L. Org. Lett. 2014, 16, 212-215.

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