Structure and membrane affinity of new amphiphilic siderophores produced by Ochrobactrum sp. SP18

Jessica D. Martin, Yusai Ito, Vanessa V. Homann, Margo Haygood, Alison Butler

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

The coastal α-proteobacterium Ochrobactrum sp. SP18 produces a suite of three citrate-derived, cell-associated amphiphilic siderophores, ochrobactins A-C. The ochrobactins are composed of a citric acid backbone amide-linked to two lysine residues. Each ε-amine of lysine is hydroxylated and acylated forming two hydroxamic acid moieties. One of the acylated appendages of each ochrobactin is (E)-2-decenoic acid. The other acylated appendages for ochrobactins A-C are (E)-2-octenoic acid, octanoic acid and (E)-2-decenoic acid, respectively. The ferric ochrobactin complexes are photoreactive in UV light, producing an oxidized ligand with loss of 46 mass units that can still coordinate Fe(III). The relative partitioning of the apo-ochrobactins, Fe(III) ochrobactins and Fe(III) photoproducts into 1,2-dimyristoyl-sn-glycero-3- phosphocholine vesicles is presented. The ochrobactins are the first example of aerobactin-based siderophores with two fatty acid appendages produced in a suite with varying acyl appendage lengths.

Original languageEnglish (US)
Pages (from-to)633-641
Number of pages9
JournalJournal of Biological Inorganic Chemistry
Volume11
Issue number5
DOIs
StatePublished - Jul 2006

Fingerprint

Ochrobactrum
Siderophores
Citric Acid
Lysine
Hydroxamic Acids
Membranes
Proteobacteria
Phosphorylcholine
Ultraviolet Rays
Amides
Ultraviolet radiation
Amines
Fatty Acids
Ligands
Acids
2-decenoic acid

Keywords

  • α-Proteobacterium
  • Ochrobactins
  • Photoreactive amphiphilic siderophore

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry

Cite this

Structure and membrane affinity of new amphiphilic siderophores produced by Ochrobactrum sp. SP18. / Martin, Jessica D.; Ito, Yusai; Homann, Vanessa V.; Haygood, Margo; Butler, Alison.

In: Journal of Biological Inorganic Chemistry, Vol. 11, No. 5, 07.2006, p. 633-641.

Research output: Contribution to journalArticle

Martin, Jessica D. ; Ito, Yusai ; Homann, Vanessa V. ; Haygood, Margo ; Butler, Alison. / Structure and membrane affinity of new amphiphilic siderophores produced by Ochrobactrum sp. SP18. In: Journal of Biological Inorganic Chemistry. 2006 ; Vol. 11, No. 5. pp. 633-641.
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