Structure of acinetoferrin, a new citrate-based dihydroxamate siderophore from Acinetobacter haemolyticus

Biometals. 1994 Apr;7(2):170-6. doi: 10.1007/BF00140488.

Abstract

From low-iron cultures of Acinetobacter haemolyticus ATCC 17906, a new hydroxamate siderophore was purified by XAD-7 adsorption followed by preparative thin layer chromatography. The siderophore, named acinetoferrin, released citric acid, 1,3-diaminopropane and (E)-2-octenoic acid upon hydrolysis with HCl, reductive hydrolysis with HI and oxidation with periodate, respectively. Structure elucidation by a combination of NMR spectroscopy and positive fast atom bombardment mass spectrometry revealed that acinetoferrin is a derivative of citric acid, both of its terminal carboxyl groups being symmetrically amide-linked with the 1-amino-3-(N-hydroxy-N-2-octenylamino)propane residues. The (E)-2-octenoic acid is novel as a component of the siderophores.

MeSH terms

  • Acinetobacter / chemistry*
  • Acinetobacter / growth & development
  • Acinetobacter / metabolism
  • Citrates / analysis
  • Citric Acid
  • Culture Media
  • Hydroxamic Acids / chemistry*
  • Hydroxamic Acids / isolation & purification
  • Hydroxamic Acids / metabolism
  • Iron / metabolism
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Siderophores / biosynthesis
  • Siderophores / chemistry*
  • Siderophores / isolation & purification
  • Spectrometry, Mass, Fast Atom Bombardment
  • Tricarboxylic Acids / chemistry*
  • Tricarboxylic Acids / isolation & purification
  • Tricarboxylic Acids / metabolism

Substances

  • Citrates
  • Culture Media
  • Hydroxamic Acids
  • Siderophores
  • Tricarboxylic Acids
  • acinetoferrin
  • Citric Acid
  • Iron