E3910
Enterobactin
from Escherichia coli, ≥98% (HPLC)
Synonyme(s) :
Enterochelin
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About This Item
Formule empirique (notation de Hill):
C30H27N3O15
Numéro CAS:
Poids moléculaire :
669.55
Code UNSPSC :
12191503
Nomenclature NACRES :
NA.25
Source biologique
Escherichia coli
Niveau de qualité
Pureté
≥98% (HPLC)
Conditions d'expédition
wet ice
Température de stockage
−20°C
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
Clé InChI
SERBHKJMVBATSJ-BZSNNMDCSA-N
Description générale
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.
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.
Actions biochimiques/physiologiques
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.
Produit(s) apparenté(s)
Réf. du produit
Description
Tarif
Code de la classe de stockage
11 - Combustible Solids
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
Certificats d'analyse (COA)
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Neal Paragas et al.
Biochimica et biophysica acta, 1823(9), 1451-1458 (2012-06-26)
Kidney damage induces the expression of a myriad of proteins in the serum and in the urine. The function of these proteins in the sequence of damage and repair is now being studied in genetic models and by novel imaging
Shubhangi Agarwal et al.
Scientific reports, 7, 42812-42812 (2017-02-22)
Molecular mechanisms of xenosiderophore and heme acquisitions using periplasmic binding protein (PBP) dependent ATP-binding cassette transporters to scavenge the essential nutrient iron are elusive yet in Vibrio cholerae. Our current study delineates the structures, dynamics and ligand binding properties of
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
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
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