Arabinose 5-phosphate analogues as mechanistic probes for Neisseria meningitidis 3-deoxy-D-manno-octulosonate 8-phosphate synthase

Bioorg Med Chem. 2008 Nov 15;16(22):9830-6. doi: 10.1016/j.bmc.2008.09.056. Epub 2008 Sep 26.

Abstract

3-Deoxy-D-manno-octulosonate 8-phosphate (KDO8P) synthase catalyses the condensation reaction between phosphoenolpyruvate and D-arabinose 5-phosphate (D-A5P) in a key step in lipopolysaccharide biosynthesis in Gram-negative bacteria. The KDO8P synthase from Neisseria meningitidis was cloned into Escherichia coli, overexpressed and purified. A variety of D-A5P stereoisomers were tested as substrates, of these only D-A5P and l-X5P were substrates. The Asn59Ala mutant of N. meningitidis KDO8P synthase was constructed and this mutant retained less than 1% of the wild-type activity. These results are consistent with a catalytic mechanism for this enzyme in which the C2 and C3 hydroxyl groups of D-A5P and Asn59 are critical.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehyde-Lyases / biosynthesis
  • Aldehyde-Lyases / isolation & purification
  • Aldehyde-Lyases / metabolism*
  • Kinetics
  • Neisseria meningitidis / enzymology*
  • Pentosephosphates / chemical synthesis
  • Pentosephosphates / chemistry*
  • Pentosephosphates / pharmacology
  • Phosphoenolpyruvate / chemistry
  • Phosphoenolpyruvate / metabolism
  • Stereoisomerism

Substances

  • Pentosephosphates
  • arabinose 5-phosphate
  • Phosphoenolpyruvate
  • 2-dehydro-3-deoxyphosphooctonate aldolase
  • Aldehyde-Lyases