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.