E3910
Enterobactin
from Escherichia coli, ≥98% (HPLC)
Synonym(s):
Enterochelin
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About This Item
Empirical Formula (Hill Notation):
C30H27N3O15
CAS Number:
Molecular Weight:
669.55
UNSPSC Code:
12191503
NACRES:
NA.25
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![(±)-(E)-4-Ethyl-2-[(Z)-hydroxyimino]-5-nitro-3-hexen-1-yl-nicotinamide ≥97%](/deepweb/assets/sigmaaldrich/product/structures/285/524/99543643-31d0-4c4f-b8da-9b1f872868ad/640/99543643-31d0-4c4f-b8da-9b1f872868ad.png)
biological source
Escherichia coli
Quality Level
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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