| Identification | Back Directory | [Name]
Enterobactin | [CAS]
28384-96-5 | [Synonyms]
Enterochelin
Enterobactin
Enterochellin
Enterobactin from Escherichia coli
(3S,7S,11S)-3,7,11-Tris(2,3-dihydroxybenzoylamino)-1,5,9-trioxacyclododecane-2,6,10-trione
N-(2,3-Dihydroxybenzoyl)cyclo[L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-]
N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)
Benzamide, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy- | [Molecular Formula]
C30H27N3O15 | [MDL Number]
MFCD16876395 | [MOL File]
28384-96-5.mol | [Molecular Weight]
669.55 |
| Chemical Properties | Back Directory | [Melting point ]
202-203° | [alpha ]
D25 +7.40° (ethanol) | [Boiling point ]
1109.1±65.0 °C(Predicted) | [density ]
1.72±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C | [form ]
Solid | [pka]
7.46±0.35(Predicted) | [color ]
White to off-white | [biological source]
Escherichia coli |
| Hazard Information | Back Directory | [Uses]
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. | [Definition]
ChEBI: Enterobactin is a macrotriolide produced by certain members of Enterobacteriaceae, e.g. Escherichia coli and Salmonella. It has a role as a bacterial metabolite and a siderophore. It is a crown compound, a member of catechols, a polyphenol and a macrotriolide. It is a conjugate acid of an enterobactin(6-) and an enterobactin(1-). | [Biological Activity]
Iron mobilization and uptake by microbes is mediated by low molecular weight complexing agents named siderophores. Enterobactin is a catechol (a benzenediolC6H4(OH)2) type siderophore produced in small quantities by Escherichia coli and related enteric bacteria when grown on iron deficient mediaand is one of the most powerful ferric ion complexing agents known. Enterobactin is a very effective sequestering agent for ironable to remove iron from proteinsinsoluble iron complexesand other siderophores. Studies of the chemistryregulationsynthesisrecognitionand transport of enterobactin make it the best-understood siderophore. |
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