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-(13)C(1)]propylphosphonic acid and 1-hydroxy-[1-(13)C(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 (13)C-labeled (up to 65 %). Hydroxyacetone is therefore considered an obligatory intermediate of the biodegradation of fosfomycin by R. huakuii PMY1.
School of Biological Sciences, The Queen's University of Belfast, Medical Biology Centre, 97 Lisburn Road, Belfast BT9 7BL, Northern Ireland. j.mcgrath@qub.ac.uk
John W
JW
McGrath
Friedrich
F
Hammerschmidt
Hanspeter
H
Kählig
Frank
F
Wuggenig
Günther
G
Lamprecht
John P
JP
Quinn
D000096:Acetone / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry* / Q000302:isolation & purification* / Q000378:metabolism; D001673:Biodegradation, Environmental; D001711:Biotransformation; D002244:Carbon / Q000737:chemistry* / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D005578:Fosfomycin / Q000737:chemistry* / Q000378:metabolism*; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry*; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D012231:Rhizobium / Q000737:chemistry* / Q000378:metabolism*; D013237:Stereoisomerism
C570944:(1R*,2R*)-1,2-dihydroxy-(1-(13)C(1))propylphosphonic acid; D000596:Amino Acids; D063065:Organophosphonates; D000096:Acetone; D005578:Fosfomycin; D002244:Carbon; D011407:Propane