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E3910

Sigma-Aldrich

Enterobactin

from Escherichia coli, ≥98% (HPLC)

Synonym(s):

Enterochelin

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About This Item

Empirical Formula (Hill Notation):
C30H27N3O15
CAS Number:
28384-96-5
Molecular Weight:
669.55
UNSPSC Code:
12191503
NACRES:
NA.25

biological source

Escherichia coli

Quality Level

200

Assay

≥98% (HPLC)

shipped in

wet ice

storage temp.

−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

InChI key

SERBHKJMVBATSJ-BZSNNMDCSA-N

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.

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

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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - Combustible Solids

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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)
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)
Pyoverdine, the major siderophore in Pseudomonas aeruginosa, evades NGAL recognition
Peek ME, et al.
Interdisciplinary perspectives on infectious diseases, 2012 (2012)
Use of a molecular decoy to segregate transport from antigenicity in the FrpB iron transporter from Neisseria meningitidis
Saleem M, et al.
PLoS ONE, 8(2), e56746-e56746 (2013)
Maud E S Achard et al.
The Biochemical journal, 454(3), 543-549 (2013-06-29)
Iron acquisition is an important aspect of the host-pathogen interaction. In the case of Salmonella it is established that catecholate siderophores are important for full virulence. In view of their very high affinity for ferric iron, functional studies of siderophores
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