Physical and structural characterization of yersiniophore, a siderophore produced by clinical isolates of Yersinia enterocolitica

Biometals. 1996 Apr;9(2):157-67. doi: 10.1007/BF00144621.

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.

Publication types

  • Comparative Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum
  • Animals
  • Chromatography, High Pressure Liquid
  • Chromatography, Ion Exchange
  • Feces / microbiology
  • Humans
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Peptides*
  • Phenols / chemistry
  • Pseudomonas aeruginosa
  • Siderophores / biosynthesis
  • Siderophores / chemistry*
  • Siderophores / isolation & purification
  • Spectrometry, Fluorescence
  • Spectrophotometry, Ultraviolet
  • Structure-Activity Relationship
  • Thiazoles*
  • Vibrio
  • Yersinia enterocolitica / isolation & purification
  • Yersinia enterocolitica / physiology*

Substances

  • Peptides
  • Phenols
  • Siderophores
  • Thiazoles
  • yersiniabactin
  • pyochelin
  • anguibactin
  • Aluminum