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

Racemic (1R*,2R*)‐1,2‐dihydroxy‐1‐¹³C₁]propylphosphonic acid and 1‐hydroxy‐1‐¹³C₁]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 ¹³C‐labeled (up to 65 %). Hydroxyacetone is therefore considered an obligatory intermediate of the biodegradation of fosfomycin by R. huakuii PMY1.