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Preparation and enzymatic recognition of α-D-mannopyranosyl-1-phosphate analogs Open Access


Other title
Mycobacterium tubeculosis
polyprenol phosphate analogs
mannopyranosyl-1-phosphate analogs
kinetic analysis
Type of item
Degree grantor
University of Alberta
Author or creator
Zou, Lu
Supervisor and department
Lowary, Todd L. (Chemistry)
Examining committee member and department
Cairo, Christopher W. (Chemistry)
Velazquez, Carlos A. (Pharmacy and Pharmaceutical Sciences)
Department of Chemistry

Date accepted
Graduation date
Master of Science
Degree level
Tuberculosis is a contagious disease, caused by Mycobacterium tuberculosis. Harsh requirements required to treat tuberculosis result from the structure of the mycobacterial cell wall. Lipoarabinomannan, an important component and major antigen of the cell wall, is able to modulate the host immune response. Among the glycosyltransferases that involved in LAM biosynthesis, a PPM-dependent α-(1→6)-ManT that transfers a mannose residue from a PPM donor to an oligosaccharide acceptor has been a research focus in our group. The PPM donor used by this enzyme is biosynthesized from mannose-1-phosphate by the action of a GDP-ManPP and a PPM synthase. To better understand how these enzymes interact with the mannose substrates, a series of methoxy and deoxy derivatives of mannose-1-phosphate were synthesized, then converted into the corresponding GDP-Man analogs. Steric interactions and hydrogen-bonding was mapped using an established colorimetric assay. Additionally, a PPM analog was synthesized and shown to be substrate for PPM synthase.
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