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Rhizobium leguminosarum bv viciae produces a novel cyclic trihydroxamate siderophore, vicibactin


Dilworth, MJ and Carson, KC and Giles, RGF and Byrne, LT and Glenn, AR, Rhizobium leguminosarum bv viciae produces a novel cyclic trihydroxamate siderophore, vicibactin, Microbiology, 144 pp. 781-791. ISSN 1350-0872 (1998) [Refereed Article]

DOI: doi:10.1099/00221287-144-3-781


Trihydroxamate siderophores were isolated from iron-deficient cultures of three strains of Rhizobium leguminosarum biovar viciae, two from Japan (WSM709, WSM710) and one from the Mediterranean (WU235), and from a Tn5-induced mutant of WSM710 (MNF7101). The first three all produced the same compound (vicibactin), which was uncharged and could be purified by solvent extraction into benzyl alcohol. The gallium and ferric complexes of vicibactin were extractable into benzyl alcohol at pH 5.0, while metal-free vicibactin could be extracted with good yield at pH 8.0. The trihydroxamate from MNF7101 (vicibactin 7101) could not be extracted into benzyl alcohol, but its cationic nature permitted purification by chromatography on Sephadex CM-25 (NH 4 + form). Relative molecular masses and empirical formulae were obtained from fast-atom-bombardment MS. The structures were derived from one- and two-dimensional 1 H and 13 C NMR spectroscopy, using DQF-COSY, NOESY, HMQC and HMBC techniques on the compounds dissolved in methanol-d 4 and DMSO-d 6 . Vicibactin proves to be a cyclic molecule containing three residues each of (R)-2,5-diamino-N 2 -acetyl-N 5 -hydroxypentanoic acid (N 2 -acetyl-N 5 -hydroxy-D-ornithine) and (R)-3-hydroxybutanoic acid, arranged alternately, with alternating ester and peptide bonds. Vicibactin 7101 differed only in lacking the acetyl substitution on the N 2 of the N 5 -hydroxyornithine, resulting in net positive charge; it was still functional as a siderophore and promoted 55 Fe uptake by iron-starved cells of WSM710 in the presence of an excess of phosphate. The rate of vicibactin biosynthesis by iron-deficient cells of WSM710 was essentially constant between pH 5.5 and 7.0, but much decreased at pH 5.0. When iron-starved cultures were supplemented with potential precursors for vicibactin, the rates of its synthesis were consistent with both β-hydroxybutyrate and ornithine being precursors. At least three genes seem likely to be involved in synthesis of vicibactin from ornithine and β-hydroxybutyrate: a hydroxylase adding the -OH group to the N 5 Of ornithine, an acetylase adding the acetyl group to the N 2 of ornithine, and a peptide synthetase system.

Item Details

Item Type:Refereed Article
Research Division:Biological Sciences
Research Group:Microbiology
Research Field:Bacteriology
Objective Division:Animal Production and Animal Primary Products
Objective Group:Pasture, browse and fodder crops
Objective Field:Pasture, browse and fodder crops not elsewhere classified
ID Code:15558
Year Published:1998
Web of Science® Times Cited:48
Deposited By:Agricultural Science
Deposited On:1998-08-01
Last Modified:2011-08-10

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