The structure of enterochelin and related 2,3-dihydroxy-N-benzoyne conjugates from Eschericha Coli

O'Brien, I.G.; Gibson, F.

doi:10.1016/0304-4165(70)90038-3

Cited by 353 publications

(218 citation statements)

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“…18,19 Compounds 2 and 3 are the partially degraded products of enterobactin, a cyclic trimer of N-2,3-dihydroxybenzoyl-L-serine responsible for virulence in some bacteria such as Salmonella typhimurium and Klebsiella pneumoniae. 11,19 To the best of our knowledge, this is the first report on the antiinvasive activities of 2 and 3. The compounds isolated in this study comprise simple building blocks, providing a starting point for optimization of new antiinvasive agents through analog synthesis.…”

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confidence: 81%

“…This unit is relatively rare in nature 11 while the 2,3-dihyroxybenzoyl group is common in siderophores produced by Gram-negative bacteria including human pathogens. 18,19 Compounds 2 and 3 are the partially degraded products of enterobactin, a cyclic trimer of N-2,3-dihydroxybenzoyl-L-serine responsible for virulence in some bacteria such as Salmonella typhimurium and Klebsiella pneumoniae.…”

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confidence: 99%

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Catechoserine, a new catecholate-type inhibitor of tumor cell invasion from Streptomyces sp.

et al. 2012

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Microbial natural products represent the primary resource for drug discovery, accounting for 420 000 bioactive compounds discovered to date. 1 The majority of microbial drug discovery research has focused on actinomycetes, in particular strains of the chemically prolific genus Streptomyces. Drug discovery efforts from actinomycetes, however, have been in decline, in part because of the relatively high frequency of the isolation of known compounds. To overcome this problem, extensive attempts have been directed toward the development of effective strain selection methods to improve the efficiency of the discovery process. 2-4 Sequence-based strain selection is one of the approaches to eliminate the strains which might be studied previously. Although it is not clear whether the phylogenic novelty is associated with the production ability of new compounds, recent studies have shown the occurrence of new metabolites in Streptomyces species that have a low 16S rRNA gene sequence homology to the known species. [5][6][7] In our continuing investigation on chemical diversity within this group, 8-10 a Streptomyces strain that shared a low 16S rRNA gene identity (96.3%) with the nearest type strain for S. albus was found to produce a new catecholate derivative, catechoserine (1), along with two known biosynthetically related metabolites, N,N¢-bis (Figure 1).The producing-strain TP-A0874 was isolated from a compost sample collected in Ishikawa, Japan, and identified as a member of the genus Streptomyces by 16S rRNA gene sequence analysis. The whole culture broth of strain TP-A0874 cultured in A-3M liquid medium was separated into the supernatant and the mycelium. The latter was then extracted with methanol, and the organic solvent was removed under reduced pressure. The remaining aqueous solution was combined with the supernatant and fractionated by HP-20 resin column chromatography. The fractions were further purified by reversed-phase HPLC to yield compounds 1-3.

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Catechoserine, a new catecholate-type inhibitor of tumor cell invasion from Streptomyces sp.

et al. 2012

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“…Enterobactin was first isolated from bacteria in 1970 by two independent research groups, Pollack and Neilands from Salmonella typhimurium [8] and O'Brien and Gibson from Escherichia coli [9]. Since then, significant advances have been made in the elucidation of the mechanisms behind the bacterial recognition and transport processes involved with the acquisition of Fe(III) from the environment via enterobactin [10,11].…”

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“…A variety of methods have been employed to probe the structure and binding of Fe(III) by enterobactin (entFe(III)). X-ray crystallography [12][13][14][15] and NMR [9,15,16] have been used for structural characterization. UV [9,14,17,18], IR [8,9,19,20] spectroscopy have been used to probe both the structure of enterobactin as well as the dependence of Fe(III) binding on solution pH.…”

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confidence: 99%

“…X-ray crystallography [12][13][14][15] and NMR [9,15,16] have been used for structural characterization. UV [9,14,17,18], IR [8,9,19,20] spectroscopy have been used to probe both the structure of enterobactin as well as the dependence of Fe(III) binding on solution pH. Other methods, such as cyclic voltametry [9,14,15,19] and circular dichroism [14,21,22] were also used for the determination of redox potentials and chirality, respectively.…”

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Infrared multiphoton dissociation of the siderophore enterobactin and its Fe(III) complex. Influence of Fe(III) binding on dissociation kinetics and relative energetics

Leslie

Daneshfar

Volmer

2007

J. Am. Soc. Mass Spectrom.

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The dissociation pathways of the siderophore enterobactin and its complex with Fe(III) were examined using infrared multiphoton dissociation (IRMPD). Under experimental conditions (pH ϭ 3.5), both compounds' electrospray spectra exhibited exclusively singly-charged anions. The compositions of the dissociation products were characterized by accurate mass measurements using Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR MS). The primary dissociation channel for both species was determined to be the loss of one serine group from the precursor molecules. To further investigate the influence of Fe(III) binding on the intramolecular interactions, dissociation kinetics and relative energetics for the loss of this serine group were determined using the focused radiation for gaseous multiphoton energytransfer (FRAGMENT) method. From the kinetic data, it was found that enterobactin was ϳseven times more reactive than its Fe(III) complex over the range of laser intensities investigated. The relative activation energies, however, exhibited similar values, ϳ7 kcal · mol Ϫ1 . These results suggest that at pH ϭ 3.5, Fe(III) interacts with only two of the three serine groups. The results from the present work are believed to be valuable for the characterization of novel siderophores as well as their associated metabolites and synthetic analogues. (J Am Soc Mass Spectrom 2007, 18, 632-641)

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Peptide siderophores

1998

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Siderophores are low molecular weight iron chelators, produced by virtually all bacteria, fungi and some plants. They serve to deliver the essential element iron, barely soluble under aerobic conditions, into microbial cells. Siderophores are therefore important secondary metabolites which are very often based on amino acids and their derivatives. Biosynthesis, transport, regulation and chemical synthesis of natural siderophores and their analogues is of considerable interest for the protein and peptide chemist. This review gives an overview of the structural classes of peptidic siderophores, along with data on their biosynthesis. On a number of representative examples, strategies and schemes of their chemical synthesis are described.

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The structure of enterochelin and related 2,3-dihydroxy-N-benzoyne conjugates from Eschericha Coli

Cited by 353 publications

References 16 publications

Catechoserine, a new catecholate-type inhibitor of tumor cell invasion from Streptomyces sp.

Catechoserine, a new catecholate-type inhibitor of tumor cell invasion from Streptomyces sp.

Infrared multiphoton dissociation of the siderophore enterobactin and its Fe(III) complex. Influence of Fe(III) binding on dissociation kinetics and relative energetics

Peptide siderophores

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