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E3910

Sigma-Aldrich

Enterobactin

from Escherichia coli, ≥98% (HPLC)

Sinônimo(s):

Enterochelin

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About This Item

Fórmula empírica (Notação de Hill):
C30H27N3O15
Número CAS:
Peso molecular:
669.55
Código UNSPSC:
12191503
NACRES:
NA.25

fonte biológica

Escherichia coli

Nível de qualidade

Ensaio

≥98% (HPLC)

Condições de expedição

wet ice

temperatura de armazenamento

−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

chave InChI

SERBHKJMVBATSJ-BZSNNMDCSA-N

Descrição geral

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.

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

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Código de classe de armazenamento

11 - Combustible Solids

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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