CAS 28384-96-5

Enterobactin

Description:

Enterobactin, with the CAS number 28384-96-5, is a high-affinity iron-chelating compound produced by various bacteria, particularly those in the Enterobacteriaceae family, such as Escherichia coli. This siderophore is a cyclic trimer of a catechol derivative, specifically composed of three 2,3-dihydroxybenzoyl groups linked by a central serine residue. Enterobactin plays a crucial role in microbial iron acquisition, allowing bacteria to thrive in iron-limited environments, such as the human body. Its structure enables it to bind iron(III) ions with exceptional affinity, facilitating the transport of iron into bacterial cells. Enterobactin is notable for its stability and solubility in aqueous solutions, which enhances its effectiveness as a chelator. Additionally, it has implications in pathogenesis, as its production can contribute to the virulence of certain bacterial strains. The study of enterobactin and similar compounds is significant in understanding microbial ecology and developing potential therapeutic strategies against bacterial infections.

Formula: C₃₀H₂₇N₃O₁₅

InChI: InChI=1/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: InChIKey=SERBHKJMVBATSJ-BZSNNMDCSA-N

SMILES: C(N[C@@H]1C(=O)OC[C@H](NC(=O)C2=C(O)C(O)=CC=C2)C(=O)OC[C@H](NC(=O)C3=C(O)C(O)=CC=C3)C(=O)OC1)(=O)C4=C(O)C(O)=CC=C4

Synonyms:

• 1,5,9-Trioxacyclododecane, benzamide deriv.
• 28384-96-5
• Benzamide, N,N′,N′′-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy-, [3S-(3R*,7R*,11R*)]-
• Benzamide, N,N′,N′′-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-
• Cyclotris(N-2,3-dihydroxybenzoyl-<span class="text-smallcaps">L</span>-seryl)
• Enterobactin
• Enterochelin
• Enterochellin
• N,N',N''-(2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris-o-pyrocatechuamide
• N,N',N''-(2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris[2,3-dihydroxy]benzamide
• N-(2,3-Dihydroxybenzoyl)-<span class="text-smallcaps">L</span>-serine trimolecular cyclic ester
• benzenecarboximidic acid, N,N',N''-[(3S,7S,11S)-2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxy-
• o-Pyrocatechuamide, N,N′,N′′-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris-
• N,N′,N′′-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris[2,3-dihydroxybenzamide]
• N,N',N''-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)
• (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*-]

Enterobactin

CAS: 28384-96-5

Enterobactin

Formula: C₃₀H₂₇N₃O₁₅

Purity: ≥95%

Molecular weight: 669.55

Ref: 54-BUP03488

Enterobactin

CAS: 28384-96-5

N,N',N''-((3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)

Formula: C₃₀H₂₇N₃O₁₅

Purity: 98% (NMR)

Molecular weight: 669.55

Ref: IN-DG00793711

Enterobactin

CAS: 28384-96-5

Enterobactin (Enterochelin) is a high-affinity siderophore that acquires iron for microbial systems.

Formula: C₃₀H₂₇N₃O₁₅

Purity: 96.73%

Color and Shape: Solid

Molecular weight: 669.55

Ref: TM-T9501

Enterobactin

CAS: 28384-96-5

Enterobactin is a siderophore that is produced by the bacteria Enterobacter. It has been shown to have various biological activities, including iron homeostasis and mitochondrial functions. Enterobactin has been used as a model system to study enterochelin synthesis in the wild-type strain of Escherichia coli. This siderophore also has antimicrobial properties and can be used as an antibiotic for bowel disease. Enterobactin binds to penicillin-binding proteins on the surface of bacterial cells, which inhibits their growth and causes cell death.

Formula: C₃₀H₂₇N₃O₁₅

Purity: Min. 95%

Molecular weight: 669.55 g/mol

Ref: 3D-FE177921

Enterobactin

CAS: 28384-96-5

Formula: C₃₀H₂₇N₃O₁₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 669.5465

Ref: IN-DA00BPLO

Enterobactin

CAS: 28384-96-5

Purity: 98% (NMR)

Molecular weight: 669.552002

Ref: 10-F863436