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
Numéro MDL:
Code UNSPSC :
12191503
Nomenclature NACRES :
NA.25
Produits recommandés
Source biologique
Escherichia coli
Niveau de qualité
Essai
≥98% (HPLC)
Conditions d'expédition
wet ice
Température de stockage
−20°C
Chaîne SMILES
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
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
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.
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
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