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

  • Author / Creator
    Zou, Lu
  • 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.

  • Subjects / Keywords
  • Graduation date
    2012-06
  • Type of Item
    Thesis
  • Degree
    Master of Science
  • DOI
    https://doi.org/10.7939/R3N58CX43
  • License
    This thesis is made available by the University of Alberta Libraries with permission of the copyright owner solely for non-commercial purposes. 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.
  • Language
    English
  • Institution
    University of Alberta
  • Degree level
    Master's
  • Department
    • Department of Chemistry
  • Supervisor / co-supervisor and their department(s)
    • Lowary, Todd L. (Chemistry)
  • Examining committee members and their departments
    • Velazquez, Carlos A. (Pharmacy and Pharmaceutical Sciences)
    • Cairo, Christopher W. (Chemistry)