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E3910

Sigma-Aldrich

Enterobactin

from Escherichia coli, ≥98% (HPLC)

Synonyme(s) :

Enterochelin

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About This Item

Formule empirique (notation de Hill):
C30H27N3O15
Numéro CAS:
28384-96-5
Poids moléculaire :
669.55
Code UNSPSC :
12191503
Nomenclature NACRES :
NA.25

Source biologique

Escherichia coli

Niveau de qualité

200

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

06693

Timestrip Plus™ -20 °C

Code de la classe de stockage

11 - Combustible Solids

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Consulter la Bibliothèque de documents

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
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
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)
Enterobactin biosynthesis in Escherichia coli: isochorismate lyase (EntB) is a bifunctional enzyme that is phosphopantetheinylated by EntD and then acylated by EntE using ATP and 2, 3-dihydroxybenzoate
Gehring AM, et al.
Biochemistry, 36(28), 8495-8503 (1997)
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