Abstract
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.
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetone / chemistry*
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Amino Acids / chemistry*
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Amino Acids / isolation & purification*
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Amino Acids / metabolism
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Biodegradation, Environmental
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Biotransformation
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Carbon / chemistry*
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Carbon / metabolism
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Chromatography, High Pressure Liquid
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Fosfomycin / chemistry*
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Fosfomycin / metabolism*
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Isotope Labeling
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Magnetic Resonance Spectroscopy
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Molecular Structure
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Organophosphonates / chemical synthesis*
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Organophosphonates / chemistry*
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Propane / analogs & derivatives*
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Propane / chemical synthesis
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Propane / chemistry
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Rhizobium / chemistry*
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Rhizobium / metabolism*
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Stereoisomerism
Substances
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(1R*,2R*)-1,2-dihydroxy-(1-(13)C(1))propylphosphonic acid
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Amino Acids
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Organophosphonates
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Acetone
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Fosfomycin
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Carbon
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Propane