Irreversible inhibition of type I dehydroquinase by substrates for type II dehydroquinase

Bioorg Med Chem Lett. 2000 Mar 6;10(5):407-9. doi: 10.1016/s0960-894x(00)00057-3.

Abstract

Mechanistic differences between type I and type II dehydroquinases have been exploited in the design of type specific inhibitors. (2R)-2-Bromo-3-dehydroquinic acid (3), (2R)-2-fluoro-3-dehydroquinic acid (5) and 2-bromo-3-dehydroshikimic acid (4), all excellent substrates for type II dehydroquinase, are shown to be irreversible inhibitors of type I dehydroquinase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Inhibitors / pharmacology*
  • Escherichia coli / enzymology
  • Hydro-Lyases / antagonists & inhibitors*
  • Hydro-Lyases / metabolism*
  • Mycobacterium tuberculosis / enzymology
  • Quinic Acid / analogs & derivatives*
  • Quinic Acid / chemical synthesis
  • Quinic Acid / pharmacology
  • Shikimic Acid / analogs & derivatives*
  • Shikimic Acid / chemical synthesis
  • Shikimic Acid / metabolism
  • Shikimic Acid / pharmacology

Substances

  • 2-bromo-3-dehydroquinic acid
  • 2-bromo-3-dehydroshikimic acid
  • 2-fluoro-3-dehydroquinic acid
  • Enzyme Inhibitors
  • Quinic Acid
  • Shikimic Acid
  • Hydro-Lyases
  • 3-dehydroquinate dehydratase