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Isolation and structural identification of the trihydroxamate siderophore vicibactin and its degradative products from Rhizobium leguminosarum ATCC 14479 bv. trifolii

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Abstract

The Rhizobia are a group of free-living soil bacteria known for their ability to symbiotically infect the roots of specific host plants as well as to produce siderophores in order to compete with other microorganisms for the limited availability of iron in the rhizosphere. In this study, Rhizobium leguminosarum ATCC 14479, which preferentially infects the red clover Trifolium pratense, was found to produce the trihydroxamate siderophore vicibactin (C33H55N6O15) under iron restricted conditions. In addition, two other iron-binding, siderophore-like compounds: C20H36N4O10, C31H55N6O15, were isolated and purified from the culture media. Due to the structural similarity of the latter compounds to vicibactin based on electrospray-mass spectrometry and nuclear magnetic resonance data, these heretofore unreported molecules are thought to be either modified or degraded products of vicibactin. Although vicibactin has previously been found to be commonly produced by other rhizobial strains, this is the first time it has been chemically characterized from a clover infecting strain of R. leguminosarum.

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Acknowledgments

We thank Allan Forsman for critical reading of the manuscript, Ralph Coffman and Robin Grindstaff for technical support, and the Department of Biology, East Tennessee State University for use of equipment. This study was supported by the Department of Health Sciences, ETSU, analytical facilities of Eastman Chemical Company, Kingsport, National Institutes of Health Grant GM 069367 (RC), and Research Development Grant 08–027 M (RC) from ETSU.

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  1. Department of Health Sciences, College of Public Health, East Tennessee State University, Johnson City, TN, 37614, USA

    William Wright & Ranjan Chakraborty

  2. Eastman Chemical Company, Building 150, Kingsport, TN, 37662, USA

    James Little & Fang Liu

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  1. William Wright
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Correspondence to Ranjan Chakraborty.

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Wright, W., Little, J., Liu, F. et al. Isolation and structural identification of the trihydroxamate siderophore vicibactin and its degradative products from Rhizobium leguminosarum ATCC 14479 bv. trifolii . Biometals 26, 271–283 (2013). https://doi.org/10.1007/s10534-013-9609-3

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