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

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

Research output: Contribution to journalArticle

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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

Fingerprint

Vibrio vulnificus
Siderophores
siderophores
Polyamines
polyamines
Salicylic acid
propane
Acids
Pathogens
acid hydrolysis
Propane
threonine
salicylic acid
Nuclear magnetic resonance spectroscopy
Mass spectrometry
nuclear magnetic resonance spectroscopy
Hydrolysis
Salicylic Acid
mass spectrometry
Threonine

Keywords

  • iron transport
  • siderophore
  • Vibrio vulnificus
  • vulnibactin

ASJC Scopus subject areas

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

Cite this

Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus. / Okujo, Noriyuki; Saito, Miki; Yamamoto, Shigeo; Yoshida, Takashi; Miyoshi, Shin-ichi; Shinoda, Sumio.

In: BioMetals, Vol. 7, No. 2, 04.1994, p. 109-116.

Research output: Contribution to journalArticle

Okujo, N, Saito, M, Yamamoto, S, Yoshida, T, Miyoshi, S & Shinoda, S 1994, 'Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus', BioMetals, vol. 7, no. 2, pp. 109-116. https://doi.org/10.1007/BF00140480
Okujo, Noriyuki ; Saito, Miki ; Yamamoto, Shigeo ; Yoshida, Takashi ; Miyoshi, Shin-ichi ; Shinoda, Sumio. / Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus. In: BioMetals. 1994 ; Vol. 7, No. 2. pp. 109-116.
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