H. Drechsel et al., STRUCTURE ELUCIDATION OF YERSINIABACTIN, A SIDEROPHORE FROM HIGHLY VIRULENT YERSINIA STRAINS, Liebigs Annalen, (10), 1995, pp. 1727-1733
From cultures of Yersinia enterocolitica H1852, an iron-complexing and
iron-transporting compound named yersiniabactin was isolated. The str
ucture of the siderophore was determined by a variety of spectroscopic
methods, including 2D NMR experiments on the metal-free ligand as wel
l 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 cent
ers, one of which is considerably epimerized. The compound forms stabl
e complexes with trivalent cations such as ferric iron and gallium.