Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis

Shigeo Yamamoto, Noriyuki Okujo, Yasuhiro Fujita, Miki Saito, Takashi Yoshida, Sumio Shinoda

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

From low-iron cultures of Vibrio fluvialis AQ 0012, two new compounds with siderophore activity were purified by XAD-7 adsorption followed by preparative TLC. Norspermidine and 2,3-dihydroxybenzoic acid were identified as constituents common to both compounds by GC-MS analyses of their acid hydrolytic products. In addition, L-threonine was identified in the hydrolysate of one compound, named fluvibactin. Based on high magnetic NMR analyses, the structure of fluvibactin was established as iV4-[2-(2,3-dihydroxyphenyl)- ftra/is-5-methyl-2-oxa2oline-4-yl]carboxy-iV1, iV7-6is-(2,3-dihydroxybenzoyl)- norspermidine, and that of the other compound as iV, iV7-w-(2,3-dihydroxybenzoyl)- norspermidine. The structures were supported by fast atom bombardment mass spectrometry. Both of the purified compounds restored growth inhibition of the producer strain and V. cholerae Non-01 induced by ethylenediamine di-(o-hydroxyphenylacetic acid), a potent synthetic chelating agent of ferric iron. 1993

Original languageEnglish
Pages (from-to)538-544
Number of pages7
JournalJournal of Biochemistry
Volume113
Issue number5
Publication statusPublished - May 1993

Fingerprint

Polyamines
Siderophores
Vibrio
Iron
ethylenediamine
Acids
Mass Spectrometry
Adsorption
Iron Chelating Agents
Fast Atom Bombardment Mass Spectrometry
Cholera
Threonine
Chelating Agents
Chelation
Mass spectrometry
Nuclear magnetic resonance
Atoms
Growth
norspermidine
fluvibactin

ASJC Scopus subject areas

  • Statistics, Probability and Uncertainty
  • Applied Mathematics
  • Physiology (medical)
  • Radiology Nuclear Medicine and imaging
  • Molecular Biology
  • Biochemistry

Cite this

Yamamoto, S., Okujo, N., Fujita, Y., Saito, M., Yoshida, T., & Shinoda, S. (1993). Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis. Journal of Biochemistry, 113(5), 538-544.

Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis. / Yamamoto, Shigeo; Okujo, Noriyuki; Fujita, Yasuhiro; Saito, Miki; Yoshida, Takashi; Shinoda, Sumio.

In: Journal of Biochemistry, Vol. 113, No. 5, 05.1993, p. 538-544.

Research output: Contribution to journalArticle

Yamamoto, S, Okujo, N, Fujita, Y, Saito, M, Yoshida, T & Shinoda, S 1993, 'Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis', Journal of Biochemistry, vol. 113, no. 5, pp. 538-544.
Yamamoto S, Okujo N, Fujita Y, Saito M, Yoshida T, Shinoda S. Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis. Journal of Biochemistry. 1993 May;113(5):538-544.
Yamamoto, Shigeo ; Okujo, Noriyuki ; Fujita, Yasuhiro ; Saito, Miki ; Yoshida, Takashi ; Shinoda, Sumio. / Structures of two polyamine-containing catecholate siderophores from vibrio fluvialis. In: Journal of Biochemistry. 1993 ; Vol. 113, No. 5. pp. 538-544.
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