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

John W. McGrath, Friedrich Hammerschmidt, Hanspeter Kaehlig, Frank Wuggenig, Guenther Lamprecht, John P. Quinn

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

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

Original languageEnglish
Pages (from-to)13341-13348
Number of pages8
JournalChemistry - A European Journal
Volume17
Issue number47
Early online date20 Oct 2011
DOIs
Publication statusPublished - 18 Nov 2011

ASJC Scopus subject areas

  • Chemistry(all)

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