28384-96-5

Basic information

• Product Name: Enterobactin
• Synonyms: Enterobactin;(3S,7S,11S)-3,7,11-Tris(2,3-dihydroxybenzoylamino)-1,5,9-trioxacyclododecane-2,6,10-trione;Enterochellin;N-(2,3-Dihydroxybenzoyl)cyclo[L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-N-(2,3-dihydroxybenzoyl)-L-Ser*-];Enterochelin
• CAS NO: 28384-96-5
• Molecular Formula: C₃₀H₂₇N₃O₁₅
• Molecular Weight: 669.55
• Mol File: 28384-96-5.mol
• Article Data: 11

Chemical Properties

• Melting Point: 202-203°
• Boiling Point: 1109.1°Cat760mmHg
• Flash Point: 624.6°C
• Appearance: /
• Density: 1.72g/cm³
• Storage Temp.: ?20°C
• PKA: 7.46±0.35(Predicted)
• CAS DataBase Reference: Enterobactin(CAS DataBase Reference)
• NIST Chemistry Reference: Enterobactin(28384-96-5)
• EPA Substance Registry System: Enterobactin(28384-96-5)

Safety Data

• Hazardous Substances Data: 28384-96-5(Hazardous Substances Data)

Usage

Description

Enterobactin is a siderophore, a small molecule secreted by bacteria to scavenge and sequester iron from their environment. It is a trilactone triserine cyclic ester that specifically binds to iron(III) with high affinity. Enterobactin is produced by various species of enteric bacteria and is known for its exceptional ability to chelate iron, making it an important molecule for bacterial survival and pathogenesis.

Uses

Used in Pharmaceutical Industry:
Enterobactin is used as a potential drug candidate for the treatment of iron-related diseases and infections due to its strong iron-binding capacity.
Used in Research Applications:
Enterobactin is used as a research tool to study the mechanisms of iron uptake and transport in bacteria, as well as the role of siderophores in bacterial pathogenesis.

Upstream product

• 56-45-1 L-serin 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 1185-53-1 tris hydrochloride 
• 104530-71-4 (3S,7S,11S)-3,7,11-triamino-1,5,9-trioxacyclodecane-2,6,10-trione trihydrochloride 
• 75299-18-2 (S)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid (S)-2-benzyloxycarbonylamino-2-[(S)-2-benzyloxycarbonylamino-2-(9,10-dioxo-9,10-dihydro-anthracen-2-ylmethoxycarbonyl)-ethoxycarbonyl]-ethyl ester 
• 74272-78-9 2,3-dibenzyloxybenzoic acid 
• 66168-82-9 (S)-2-Benzyloxycarbonylamino-3-hydroxy-propionic acid (S)-2-benzyloxycarbonylamino-2-((S)-2-benzyloxycarbonylamino-2-carboxy-ethoxycarbonyl)-ethyl ester 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 
• 66168-83-0 ((3S,7S,11S)-7,11-Bis-benzyloxycarbonylamino-2,6,10-trioxo-1,5,9-trioxa-cyclododec-3-yl)-carbamic acid benzyl ester 
• 174145-57-4 N,N-Dibenzyl-L-serine cyclic trimer 
• 69146-58-3 2,3-bis(benzyloxy)benzoyl chloride 
• 88109-07-3 tris(N-trityl-L-serine) trilactone 
• 88195-64-6 Hexa-O-benzylenterochelin 

Downstream Products

• 851900-99-7 N,N'-((3S,7S,11S)-11-(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7-diyl)bis(2,3-dihydroxybenzamide) 
• 768386-89-6 (S,R,R,S,R)-N,N'-((3S,7S,11S)-11-(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7-diyl)bis(2,3-dihydroxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzamide) 
• 30414-16-5 N,N',N''-tris(2,3-dihydroxybenzoyl)-O-L-seryl-O-L-seryl L-serine 
• 7724-78-9 2,3-dihydroxybenzoyl-L-serine 

Relevant articles and documents

Si-enterobactin from the endophytic Streptomyces sp. KT-S1-B5-a potential silicon transporter in Nature?

Si-enterobactin (2a), a hexacoordinated complex of the siderophore enterobactin (2b) with silicon as the central atom, was isolated from an endophytic Streptomyces sp. occurring in Piper guinensis roots. The structure and absolute configuration were determined from NMR and MS data, and by X-ray diffraction. The orientation of the molecule along the pseudo-3-fold axis shows that the coordination environment of the silicon atom complexed with three bidentate ligands is Δ. We assume that 2a or related complexes may be involved in the transport of silicon in plants, diatoms, or other silicon-dependent organisms. The Royal Society of Chemistry.

Facile and Versatile Chemoenzymatic Synthesis of Enterobactin Analogues and Applications in Bacterial Detection

Siderophores, such as enterobactin (Ent), are small molecules that can be selectively imported into bacteria along with iron by cognate transporters. Siderophore conjugates are thus a promising strategy for delivering functional reagents into bacteria. In this work, we present an easy-to-perform, one-pot chemoenzymatic synthesis of functionalized monoglucosylated enterobactin (MGE). When functionalized MGE is conjugated to a rhodamine fluorophore, which affords RhB-Glc-Ent, it can selectively label Gram-negative bacteria that utilize Ent, including some E. coli strains and P. aeruginosa. V. cholerae, a bacterium that utilizes linearized Ent, can also be weakly targeted. Moreover, the targeting is effective under iron-limiting but not iron-rich conditions. Our results suggest that the RhB-Glc-Ent probe is sensitive not only to the bacterial strain but also to the iron condition in the environment.

Structural change of the enterobactin synthetase in crowded solution and its relation to crowding-enhanced product specificity in nonribosomal enterobactin biosynthesis

Significant conformational change is detected by circular dichroism and fluorimetry for the major component of the enterobactin synthetase in crowded solutions mimicking the intracellular environment. The structural change correlates well with the extent of the crowding-induced side product suppression in nonribosomal enterobactin synthesis. In contrast, protein-stabilizing solvophobic agents such as glycerol have no effect on the formation of side products, excluding crowding-induced protein stability as a cause for the observed enhancement of the product specificity of the synthetase. These results strongly support that macromolecular crowding is an indispensable physiological factor for normal functioning of the nonribosomal enterobactin synthetase by altering the active sites to increase its product specificity.