title: Structure of pseudobactin A214, a siderophore from a bean-deleterious Pseudomonas.
abstract: Bean-deleterious Pseudomonas A214 produced the extracellular yellow-green, fluorescent siderophore [microbial iron(III) transport agent] pseudobactin A214 under iron-limiting conditions. Pseudobactin A214 has a molecular formula of C46H64N13O22 and a molecular mass of 1151 g/mol. Pseudobactin A214 contained an N-blocked linear octapeptide with the amino acid sequence Ser-Ala-Gly-Ser-Ala-threo-beta-OH-Asp-L-allo-Thr-N delta-OH-Orn with a yellow-green, fluorescent quinoline derivative attached via an amide bond to the amino terminus. A succinamide group was linked to carbon 3 of the quinoline derivative. Sequencing was accomplished by two-dimensional NMR spectroscopy and by Edman degradation of smaller peptides obtained from partial acid hydrolysis. Since pseudobactin A214 was not affected by nonspecific proteolytic enzymes, it might contain D-amino acids. The three bidentate iron-(III)-chelating groups consisted of a 1,2-dihydroxy aromatic group in the quinoline chromophore, an alpha-hydroxy acid group present as beta-hydroxyaspartic acid, and a hydroxamate group derived from N delta-acetyl-N delta-hydroxyornithine. The chemical structure of pseudobactin A214 is remarkably similar to those of pseudobactin and pseudobactin 7SR1, the siderophores of plant growth promoting and plant-deleterious Pseudomonas B10 and Pseudomonas 7SR1, respectively.
mesh_terms: D000595:Amino Acid Sequence; D007887:Fabaceae; D007476:Ionophores / Q000302:isolation & purification*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009842:Oligopeptides / Q000302:isolation & purification*; D010935:Plant Diseases; D010944:Plants; D010946:Plants, Medicinal; D011549:Pseudomonas / Q000472:pathogenicity
chemical_list: D007476:Ionophores; D009842:Oligopeptides; C050272:pseudobactin A214