Issue 9, 2009
From the journal:

Organic & Biomolecular Chemistry

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

John W. McGrath,a   Friedrich Hammerschmidt,*b   Werner Preusser,b   John P. Quinn*a  and  Anna Schweiferb  

* Corresponding authors

a School of Biology and Biochemistry, The Queen's University of Belfast, Medical Biology Centre, 97 Lisburn Rd., Belfast, Northern Ireland
E-mail: j.quinn@qub.ac.uk
Fax: +44 28 90975877
Tel: +44 28 90972287

b University of Vienna, Institute of Organic Chemistry, Währingerstrasse 38, Vienna, Austria
E-mail: friedrich.hammerschmidt@univie.ac.at
Fax: +43 (1) 4277 9521
Tel: +43 (1) 4277 52105

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

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Article information

DOI
https://doi.org/10.1039/B821829C
Article type
Paper
Submitted
05 Dec 2008
Accepted
23 Feb 2009
First published
23 Mar 2009

Org. Biomol. Chem., 2009,7, 1944-1953

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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

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