title: Physical and structural characterization of yersiniophore, a siderophore produced by clinical isolates of Yersinia enterocolitica.
abstract: Clinical isolates of Yersinia enterocolitca, which belong to mouse-lethal serotypes, produce the siderophore yersiniophore. Siderophore production was shown to be iron regulated and to reach maximum production in late log phase. Yersiniophore is a fluorescent siderophore with maximum excitation at 270 nm and a major emission peak at 428 nm. Absorption maxima were seen at 210 and 250 nm with a low broad peak from 280 to 320 nm. Purification of unchelated yersiniophore for structural analysis was made difficult by low yields (1-2 mg mg-1), and susceptibility to acid hydrolysis, oxidation and possibly polymerization. Yersinophore was therefore purified as an Al3+ chelate, which was found to be stable in solution for several weeks. To purify Al(3+)-yersinophore, unchelated yersiniophore was first extracted from culture supernatants with dichloromethane, concentrated by rotary evaporation and adsorbed to a DEAE-sephacel column. Al(3+)-yersiniophore was eluted with 0.01 M AlCl3 and further purified by HPLC. The structure was established by a combination of elemental analysis, high resolution mass spectrometry and two-dimensional NMR experiments. Yersiniophore is a phenolate-thiazole siderophore with the formula C21H24N3O4S3Al and a molecular weight of 505.07404 when chelated to Al3+. The structure of yersiniophore was determined to be closely related to the structures of pyochelin, produced by Pseudomonas aeruginosa, and anguibactin, produced by Vibrio anguillarum.
authors: Department of Microbiology, University of Calgary, Alberta, Canada.
authors: C E
authors: CE
authors: Chambers
authors: D D
authors: DD
authors: McIntyre
authors: M
authors: M
authors: Mouck
authors: P A
authors: PA
authors: Sokol
mesh_terms: D000535:Aluminum; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002852:Chromatography, Ion Exchange; D005243:Feces / Q000382:microbiology; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D051379:Mice; D010455:Peptides; D010636:Phenols / Q000737:chemistry; D011550:Pseudomonas aeruginosa; D017262:Siderophores / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification; D013050:Spectrometry, Fluorescence; D013056:Spectrophotometry, Ultraviolet; D013329:Structure-Activity Relationship; D013844:Thiazoles; D014733:Vibrio; D015008:Yersinia enterocolitica / Q000302:isolation & purification / Q000502:physiology*
chemical_list: D010455:Peptides; D010636:Phenols; D017262:Siderophores; D013844:Thiazoles; C104398:yersiniabactin; C025316:pyochelin; C049469:anguibactin; D000535:Aluminum