E3910
Enterobactin
from Escherichia coli, ≥98% (HPLC)
Sinónimos:
Enterochelin
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About This Item
Fórmula empírica (notación de Hill):
C30H27N3O15
Número CAS:
Peso molecular:
669.55
MDL number:
UNSPSC Code:
12191503
NACRES:
NA.25
Nombre del producto
Enterobactin, from Escherichia coli, ≥98% (HPLC)
SMILES string
N([C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)c4c(c(ccc4)O)O)NC(=O)c3c(c(ccc3)O)O)C(=O)c1c(c(ccc1)O)O
InChI
1S/C30H27N3O15/c34-19-7-1-4-13(22(19)37)25(40)31-16-10-46-29(44)18(33-27(42)15-6-3-9-21(36)24(15)39)12-48-30(45)17(11-47-28(16)43)32-26(41)14-5-2-8-20(35)23(14)38/h1-9,16-18,34-39H,10-12H2,(H,31,40)(H,32,41)(H,33,42)/t16-,17-,18-/m0/s1
InChI key
SERBHKJMVBATSJ-BZSNNMDCSA-N
biological source
Escherichia coli
assay
≥98% (HPLC)
shipped in
wet ice
storage temp.
−20°C
Quality Level
Application
Enterobactin has been used:
- as a positive control in tryptophan fluorescence quenching experiments
- as a reference standard in high performance liquid chromatography to quantify Kosakonia radicincitans culture medium siderophores
- in the crystallization reservoir to remove iron contamination in the medium and in Fe-enterbactin binding studies
This preparation of enterobactin is not bound to iron and will bind to Fe3+ and Fe2+ in solution.
Biochem/physiol Actions
Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type iron siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media. It is one of the most powerful ferric ion complexing agents known.
Iron mobilization and uptake by microbes is mediated by low molecular weight complexing agents named siderophores. Enterobactin is a catechol (a benzenediol, C6H4(OH)2) type siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient media, and is one of the most powerful ferric ion complexing agents known. Enterobactin is a very effective sequestering agent for iron, able to remove iron from proteins, insoluble iron complexes, and other siderophores. Studies of the chemistry, regulation, synthesis, recognition, and transport of enterobactin make it the best-understood siderophore.
General description
Enterobactin synthesis occurs via nonribosomal peptide synthetases. The precursor chorismic acid is converted to intermediates isochorismate, 2,3-dihydro-2,3-dihydroxybenzoate and 2,3-dihydroxybenzoic acid (DHB). Final step involves the DHB and L-serine amide linkage. A total of six enzymes (ent A −F) mediate enterobactin biosynthesis.
Clase de almacenamiento
11 - Combustible Solids
flash_point_f
Not applicable
flash_point_c
Not applicable
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Enterobactin: an archetype for microbial iron transport
Raymond KN, et al.
Proceedings of the National Academy of Sciences of the USA, 100(7), 3584-3588 (2003)
Beata Krawczyk et al.
Pathogens (Basel, Switzerland), 9(5) (2020-04-30)
Escherichia coli were isolated from three patients with chronic rhinosinusitis (CRS) by intraoperative sinus tissue biopsy. Taking into account the unusual replicative niche and previous treatment failures, it was decided to focus on the virulence and drug resistance of these
Tobias Fuhrer et al.
Molecular systems biology, 13(1), 907-907 (2017-01-18)
Metabolism is one of the best-understood cellular processes whose network topology of enzymatic reactions is determined by an organism's genome. The influence of genes on metabolite levels, however, remains largely unknown, particularly for the many genes encoding non-enzymatic proteins. Serendipitously
Emily M Saad et al.
Nature communications, 8(1), 1590-1590 (2017-11-19)
The chromium (Cr) isotope system has emerged as a potential proxy for tracing the Earth's atmospheric evolution based on a redox-dependent framework for Cr mobilization and isotope fractionation. Although studies have demonstrated that redox-independent pathways can also mobilize Cr, no
Production of siderophores by the bacterium Kosakonia radicincitans and its application to control of phytopathogenic fungi
Lambrese Y, et al.
bioresource technology reports, 3(28), 82-87 (2018)
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