Jump to main content
Jump to site search

Issue 9, 2009
Previous Article Next Article

Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically

Author affiliations

Abstract

The first step of the mineralisation of fosfomycin by R. huakuii PMY1 is hydrolytic ring opening with the formation of (1R,2R)-1,2-dihydroxypropylphosphonic acid. This phosphonic acid and its three stereoisomers were synthesised by chemical means and tested as their ammonium salts for mineralisation as evidenced by release of Pi. Only the (1R,2R)-isomer was degraded. A number of salts of phosphonic acids such as (±)-1,2-epoxybutyl-, (±)-1,2-dihydroxyethyl-, 2-oxopropyl-, (S)-2-hydroxypropyl-, (±)-1-hydroxypropyl- and (±)-1-hydroxy-2-oxopropylphosphonic acid were synthesised chemically, but none supported growth. In vitro C–P bond cleavage activity was however detected with the last phosphonic acid. A mechanism involving phosphite had to be discarded as it could not be used as a phosphorus source. R. huakuii PMY1 grew well on (R)- and (S)-lactic acid and hydroxyacetone, but less well on propionic acid and not on acetone or (R)- and (±)-1,2-propanediol. The Pi released from (1R,2R)-1,2-dihydroxypropylphosphonic acid labelled with one oxygen-18 in the PO3H2group did not stay long enough in the cells to allow complete exchange of 18O for 16O by enzymic turnover.

Graphical abstract: Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically

Back to tab navigation

Publication details

The article was received on 05 Dec 2008, accepted on 23 Feb 2009 and first published on 23 Mar 2009


Article type: Paper
DOI: 10.1039/B821829C
Citation: Org. Biomol. Chem., 2009,7, 1944-1953
  •   Request permissions

    Studies on the biodegradation of fosfomycin: Growth of Rhizobium huakuii PMY1 on possible intermediates synthesised chemically

    J. W. McGrath, F. Hammerschmidt, W. Preusser, J. P. Quinn and A. Schweifer, Org. Biomol. Chem., 2009, 7, 1944
    DOI: 10.1039/B821829C

Search articles by author

Spotlight

Advertisements