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Furanose sugar nucleotides, Campylobacter jejuni, Mycobacterium tuberculosis

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.





Autor: Snitynsky, Ryan Blake

Fuente: https://era.library.ualberta.ca/


Introducción



University of Alberta Synthesis of Furanose Sugar Nucleotides from Mycobacterium tuberculosis and Campylobacter jejuni by Ryan Blake Snitynsky A thesis submitted to the Faculty of Graduate Studies and Research in partial fulfillment of the requirements for the degree of Master of Science Department of Chemistry © Ryan Blake Snitynsky Spring 2014 Edmonton, Alberta 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 authors prior written permission . Dedicated to Anne Snitynsky and Mita Dasog; One gave me roots And the other gave me wings. 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 deve...





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