Sugar nucleotide recognition by Klebsiella pneumoniae UDP-D-galactopyranose mutase: Fluorinated substrates, kinetics and equilibria

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Errey, J.C. and Mann, M.C. and Fairhurst, S.A. and Hill, L. and McNeil, M.R. and Naismith, J.H. and Percy, J.M. and Whitfield, C. (2009) Sugar nucleotide recognition by Klebsiella pneumoniae UDP-D-galactopyranose mutase: Fluorinated substrates, kinetics and equilibria. Organic and Biomolecular Chemistry, 7 (5). pp. 1009-1016. ISSN 1477-0520 (http://dx.doi.org/10.1039/b815549f)

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Abstract

A series of selectively fluorinated and other substituted UDP-D-galactose derivatives have been evaluated as substrates for Klebsiella pneumoniae UDP-D-galactopyranose mutase. This enzyme, which catalyses the interconversion of the pyranose and furanose forms of galactose as its UDP adduct, is a prospective drug target for a variety of microbial infections. We show that none of the 2''-, 3''- or 6''-hydroxyl groups of UDP-D-galactopyranose are essential for substrate binding and turnover. However, steric factors appear to play an important role in limiting the range of substitutions that can be accommodated at C-2'' and C-6'' of the sugar nucleotide substrate. Attempts to invert the C-2'' stereochemistry from equatorial to axial, changing D-galacto- to D-talo-configuration, in an attempt to exploit the higher percentage of furanose at equilibrium in the talo-series, met with no turnover of substrate.

ORCID iDs

Errey, J.C., Mann, M.C., Fairhurst, S.A., Hill, L., McNeil, M.R., Naismith, J.H., Percy, J.M. ORCID logoORCID: https://orcid.org/0000-0001-8636-2704 and Whitfield, C.;
  • Item type:Article
    ID code:19266
    Dates:
    Date
    Event
    2009
    Published
    Notes:Strathprints' policy is to record up to 8 authors per publication, plus any additional authors based at the University of Strathclyde. More authors may be listed on the official publication than appear in the Strathprints' record.
    Subjects:Science > Chemistry
    Department:Faculty of Science > Pure and Applied Chemistry
    Depositing user: Strathprints Administrator
    Date deposited:29 Sep 2010 10:56
    Last modified:11 Nov 2024 09:23
    URI:https://strathprints.strath.ac.uk/id/eprint/19266
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