Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus

Noriyuki Okujo, Miki Saito, Shigeo Yamamoto, Takashi Yoshida, Shin-ichi Miyoshi, Sumio Shinoda

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Abstract

A new siderophore named vulnibactin has been isolated from low iron cultures of Vibrio vulnificus, a human pathogen. The structure was established as N-[3-(2,3-dihydroxybenzamido)propyl]-1,3-bis[2-(2-hydroxyphenyl)-trans-5-methyl-2-oxazoline-4-carboxamido]propane by a combination of acid hydrolysis, nuclear magnetic resonance spectroscopy and positive fast atom bombardment mass spectrometry. Vulnibactin is characterized as containing one residue of 2,3-dihydroxybenzoic acid as well as two residues of salicylic acid, both of which are involved in the formation of oxazoline rings with l-threonine bound to a norspermidine backbone. In addition, two other compounds with siderophore activity were purified and their structures were also determined. These two compounds provided further support for the structure of vulnibactin.

Original languageEnglish
Pages (from-to)109-116
Number of pages8
JournalBioMetals
Volume7
Issue number2
DOIs
Publication statusPublished - Apr 1994

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Keywords

  • iron transport
  • siderophore
  • Vibrio vulnificus
  • vulnibactin

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Agricultural and Biological Sciences(all)

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