Degradation pathway and generation of monohydroxamic acids from the trihydroxamate siderophore deferrioxamine B

Siderophores are avid ferric ion-chelating molecules that sequester the metal for microbes. Microbes elicit siderophores in numerous and different environments, but the means by which these molecules reenter the carbon and nitrogen cycles is poorly understood. The metabolism of the trihydroxamic aci...

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Published in:Applied and Environmental Microbiology 2004-02, Vol.70 (2), p.831-836
Main Authors: Pierwola, A, Krupinski, T, Zalupski, P, Chiarelli, M, Castignetti, D
Format: Article
Language:English
Subjects:
Alphaproteobacteria - enzymology
Alphaproteobacteria - isolation & purification
Alphaproteobacteria - metabolism
Biodegradation
Biodegradation, Environmental
Biological and medical sciences
Chromatography, High Pressure Liquid
deferoxamine
Deferoxamine - chemistry
Deferoxamine - metabolism
Fundamental and applied biological sciences. Psychology
Hydrolases - metabolism
hydroxamic acids
Hydroxamic Acids - chemistry
Hydroxamic Acids - metabolism
Mass Spectrometry
Mesorhizobium loti
metabolism
metabolites
Microbiology
Siderophores - chemistry
Siderophores - metabolism
soil bacteria
Soil Microbiology
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Summary:Siderophores are avid ferric ion-chelating molecules that sequester the metal for microbes. Microbes elicit siderophores in numerous and different environments, but the means by which these molecules reenter the carbon and nitrogen cycles is poorly understood. The metabolism of the trihydroxamic acid siderophore deferrioxamine B by a Mesorhizobium loti isolated from soil was investigated. Specifically, the pathway by which the compound is cleaved into its constituent monohydroxamates was examined. High-performance liquid chromatography and mass-spectroscopy analyses demonstrated that M. loti enzyme preparations degraded deferrioxamine B, yielding a mass-to-charge (m/z) 361 dihydroxamic acid intermediate and an m/z 219 monohydroxamate. The dihydroxamic acid was further degraded to yield a second molecule of the m/z 219 monohydroxamate as well as an m/z 161 monohydroxamate. These studies indicate that the dissimilation of deferrioxamine B by M. loti proceeds by a specific, achiral degradation and likely represents the reversal by which hydroxamate siderophores are thought to be synthesized.
ISSN:0099-2240
1098-5336
DOI:10.1128/AEM.70.2.831-836.2004