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Merck
모든 사진(1)

주요 문서

E3910

Sigma-Aldrich

Enterobactin

from Escherichia coli, ≥98% (HPLC)

동의어(들):

Enterochelin

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About This Item

실험식(Hill 표기법):
C30H27N3O15
CAS Number:
Molecular Weight:
669.55
MDL number:
UNSPSC 코드:
12191503
NACRES:
NA.25

생물학적 소스

Escherichia coli

Quality Level

분석

≥98% (HPLC)

배송 상태

wet ice

저장 온도

−20°C

SMILES string

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

InChI key

SERBHKJMVBATSJ-BZSNNMDCSA-N

일반 설명

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.

애플리케이션

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.

생화학적/생리학적 작용

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.

관련 제품

제품 번호
설명
가격

Storage Class Code

11 - Combustible Solids

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable


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문서 라이브러리 방문

Enterobactin: an archetype for microbial iron transport
Raymond KN, et al.
Proceedings of the National Academy of Sciences of the USA, 100(7), 3584-3588 (2003)
Beata Krawczyk et al.
Pathogens (Basel, Switzerland), 9(5) (2020-04-30)
Escherichia coli were isolated from three patients with chronic rhinosinusitis (CRS) by intraoperative sinus tissue biopsy. Taking into account the unusual replicative niche and previous treatment failures, it was decided to focus on the virulence and drug resistance of these
Emily M Saad et al.
Nature communications, 8(1), 1590-1590 (2017-11-19)
The chromium (Cr) isotope system has emerged as a potential proxy for tracing the Earth's atmospheric evolution based on a redox-dependent framework for Cr mobilization and isotope fractionation. Although studies have demonstrated that redox-independent pathways can also mobilize Cr, no
Tobias Fuhrer et al.
Molecular systems biology, 13(1), 907-907 (2017-01-18)
Metabolism is one of the best-understood cellular processes whose network topology of enzymatic reactions is determined by an organism's genome. The influence of genes on metabolite levels, however, remains largely unknown, particularly for the many genes encoding non-enzymatic proteins. Serendipitously
Agustín Estrada-Peña et al.
Pathogens (Basel, Switzerland), 9(4) (2020-04-26)
Ixodes scapularis ticks harbor microbial communities including pathogenic and non-pathogenic microbes. Pathogen infection increases the expression of several tick gut proteins, which disturb the tick gut microbiota and impact bacterial biofilm formation. Anaplasma phagocytophilum induces ticks to express I. scapularis

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