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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

Authors

  • Dr. John W. McGrath,

    1. School of Biological Sciences, The Queen's University of Belfast, Medical Biology Centre, 97 Lisburn Road, Belfast BT9 7BL (Northern Ireland), Fax: (+44) 28-90975877
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  • Prof. Dr. Friedrich Hammerschmidt,

    Corresponding author
    1. Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria), Fax: (+43) 1-4277-9521
    • Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria), Fax: (+43) 1-4277-9521
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  • Prof. Dr. Hanspeter Kählig,

    1. Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria), Fax: (+43) 1-4277-9521
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  • Dr. Frank Wuggenig,

    1. Institute of Organic Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria), Fax: (+43) 1-4277-9521
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  • Prof. Dr. Günther Lamprecht,

    1. Institute of Analytical Chemistry, University of Vienna, Währingerstrasse 38, 1090 Vienna (Austria)
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  • Dr. John P. Quinn

    Corresponding author
    1. School of Biological Sciences, The Queen's University of Belfast, Medical Biology Centre, 97 Lisburn Road, Belfast BT9 7BL (Northern Ireland), Fax: (+44) 28-90975877
    • School of Biological Sciences, The Queen's University of Belfast, Medical Biology Centre, 97 Lisburn Road, Belfast BT9 7BL (Northern Ireland), Fax: (+44) 28-90975877
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Abstract

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.

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