Fluorinated substrates result in variable leakage of a reaction intermediate during catalysis by dehydroquinate synthase

Org Biomol Chem. 2011 Apr 21;9(8):2861-7. doi: 10.1039/c0ob01141j. Epub 2011 Mar 8.


Incubation of (3S)-3-fluoro-3-deoxy-D-arabino-heptulosonate 7-phosphate with dehydroquinate (DHQ) synthase from three phylogenetically distinct sources resulted in the production of (6S)-6-fluoroDHQ and its epimer 1-epi-(6S)-6-fluoroDHQ. The differences in the product ratios of the reactions catalysed by each enzyme imply that 1-epi-(6S)-6-fluoroDHQ formation occurs by an unusual partial leakage of a reaction intermediate from the enzyme.

MeSH terms

  • Aspergillus nidulans / enzymology*
  • Biocatalysis*
  • Escherichia coli / enzymology*
  • Fluorine Compounds / chemistry*
  • Fluorine Compounds / metabolism
  • Isomerism
  • Molecular Structure
  • Phosphorus-Oxygen Lyases / metabolism*
  • Pyrococcus furiosus / enzymology*
  • Substrate Specificity


  • Fluorine Compounds
  • Phosphorus-Oxygen Lyases