Studies on the biodegradation of fosfomycin: synthesis of 13C-labeled intermediates, feeding experiments with Rhizobium huakuii PMY1, and isolation of labeled amino acids from cell mass by HPLC

Chemistry. 2011 Nov 18;17(47):13341-8. doi: 10.1002/chem.201100725. Epub 2011 Oct 20.

Abstract

Racemic (1R*,2R*)-1,2-dihydroxy-[1-(13)C(1)]propylphosphonic acid and 1-hydroxy-[1-(13)C(1)]acetone were synthesized and fed to R. huakuii PMY1. Alanine and a mixture of valine and methionine were isolated as their N-acetyl derivatives from the cell hydrolysate by reversed-phase HPLC and analyzed by NMR spectroscopy. It was found that the carbon atoms of the respective carboxyl groups were highly (13)C-labeled (up to 65 %). Hydroxyacetone is therefore considered an obligatory intermediate of the biodegradation of fosfomycin by R. huakuii PMY1.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetone / chemistry*
  • Amino Acids / chemistry*
  • Amino Acids / isolation & purification*
  • Amino Acids / metabolism
  • Biodegradation, Environmental
  • Biotransformation
  • Carbon / chemistry*
  • Carbon / metabolism
  • Chromatography, High Pressure Liquid
  • Fosfomycin / chemistry*
  • Fosfomycin / metabolism*
  • Isotope Labeling
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry*
  • Propane / analogs & derivatives*
  • Propane / chemical synthesis
  • Propane / chemistry
  • Rhizobium / chemistry*
  • Rhizobium / metabolism*
  • Stereoisomerism

Substances

  • (1R*,2R*)-1,2-dihydroxy-(1-(13)C(1))propylphosphonic acid
  • Amino Acids
  • Organophosphonates
  • Acetone
  • Fosfomycin
  • Carbon
  • Propane