From cultures of Yersinia enterocolitica H1852, an iron‐complexing and iron‐transporting compound named yersiniabactin was isolated. The structure of the siderophore was determined by a variety of spectroscopic methods, including 2D NMR experiments on the metal‐free ligand as well as its gallium complex. The metal‐free ligand, derivatives, as well as iron and gallium complexes were examined by high‐resolution FAB‐MS, API‐MS, API‐MS/MS and GC‐MS. The novel siderophore contains a benzene and a thiazolidine ring, as well as two thiazoline rings (Figure 1). Its stereochemistry is noteworthy for the presence of five chiral centers, one of which is considerably epimerized. The compound forms stable complexes with trivalent cations such as ferric iron and gallium.

This paper describes the chemical characterization of staphyloferrin B, a new complexone type siderophore isolated from low iron cultures of Staphylococcus hyicus DSM 20459. Purification of the very hydrophilic metabolite was achieved by anion exchange high performance liquid chromatography HPLC. Mass spectrometry showed a molecular mass of 448 amu. Hydrolysis with 8 M HCl revealed the presence of L-2,3-diaminopropionic acid, citrate, ethylenediamine and succinic semialdehyde. The connections between the four building blocks were determined by two-dimensional nuclear magnetic resonance measurements. UV/Vis and circular dichroism spectra are consistent with the proposed structure, which could also be confirmed by precursor feeding. The siderophore activity of staphyloferrin B was demonstrated by iron transport measurements.

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A highly hydrophilic compound was isolated from low iron culture broth of Staphylococcus hyicus DSM 20459 which exhibits siderophore activity to the producer and 37 other staphylococci. The previously unknown metabolite was designated staphyloferrin A and constists of two molecules of citric acid, each linked to d‐ornitine by an amide bond. Using an iron‐pair HPLC‐system we detected staphyloferrin A and a second iron regulated compound (staphyloferrin B) in the culture fluid of several Staphylococcus strains. We found no evidence that staphylococci synthesize catecholor hydroxamate‐type siderophores.

A highly hydrophilic compound with siderophore activity has been isolated from the supernatant of Staphylococcus hyicus DSM 20459 grown under iron-restricted conditions. The metabolite, named staphyloferrin B, is strictly iron-regulated and produced by a large variety of staphylococci strains. In vivo iron transport measurements and the growth-promoting activity in a bioassay establish staphyloferrin B as the second siderophore for staphylococci besides the previously described staphyloferrin A. The structure elucidation revealed 2,3-diaminopropionic acid, citrate, ethylenediamine and 2-ketoglutaric acid as structural components of the compound. Thus, staphyloferrin B is a structurally new siderophore of the complexone type.