Frequency and Mechanism of Resistance to Antibacterial Action of ZM 240401, (6S)-6-fluoro-shikimic Acid

Antimicrob Agents Chemother. 1995 Jan;39(1):87-93. doi: 10.1128/aac.39.1.87.


Spontaneous resistance to (6S)-6-fluoro-shikimic acid arose in Escherichia coli and other enterobacteria at high frequencies, between 10(-5) and 10(-4). Two resistant variants of E. coli were tested for their susceptibilities to the diastereomeric compound, (6R)-6-fluoro-shikimate, and both of them had become resistant to this compound as well. (6S)-6-Fluoro-shikimate-resistant variants of E. coli generally failed to transport [14C]shikimate. In E. coli K-12, (6S)-6-fluoro-shikimate resistance cotransduced with his at the same frequency as shiA, a gene locus that governs shikimate transport phenotypes. We propose that the loss of susceptibility to (6S)-6-fluoro-shikimic acid in spontaneous resistant variants is due to the loss of activity of the transport system by which it enters the bacterial cytoplasm.

Publication types

  • Comparative Study

MeSH terms

  • Anti-Bacterial Agents / pharmacokinetics
  • Anti-Bacterial Agents / pharmacology*
  • Drug Resistance, Microbial
  • Enterobacter / drug effects*
  • Escherichia coli / drug effects
  • Escherichia coli / metabolism
  • Microbial Sensitivity Tests
  • Shikimic Acid / analogs & derivatives*
  • Shikimic Acid / pharmacokinetics
  • Shikimic Acid / pharmacology
  • Stereoisomerism


  • 6-fluoroshikimic acid
  • Anti-Bacterial Agents
  • Shikimic Acid