Enterobactin

Base Information

• Chemical Name: Enterobactin
• CAS No.: 28384-96-5
• Molecular Formula: C30H27 N3 O15
• Molecular Weight: 669.555
• UNII: 35C9R2N24F
• DSSTox Substance ID: DTXSID40182617
• Nikkaji Number: J17.543I
• Wikipedia: Enterobactin
• Wikidata: Q523354
• Metabolomics Workbench ID: 45322
• ChEMBL ID: CHEMBL432995
• Mol file: 28384-96-5.mol

Synonyms:Enterobactin;Enterochelin

Chemical Property of Enterobactin

Chemical Property:

• Melting Point: 202-203°
• Boiling Point: 1109.1°Cat760mmHg
• PKA: 7.46±0.35(Predicted)
• Flash Point: 624.6°C
• PSA: 298.05000
• Density: 1.72g/cm³
• LogP: 0.98340
• Storage Temp.: ?20°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 15
• Rotatable Bond Count: 6
• Exact Mass: 669.14421716
• Heavy Atom Count: 48
• Complexity: 1060

Purity/Quality:

99% ^*data from raw suppliers

Enterobactin ≥98% (HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(=O)OCC(C(=O)OCC(C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O
• Isomeric SMILES: C1[C@@H](C(=O)OC[C@@H](C(=O)OC[C@@H](C(=O)O1)NC(=O)C2=C(C(=CC=C2)O)O)NC(=O)C3=C(C(=CC=C3)O)O)NC(=O)C4=C(C(=CC=C4)O)O

Technology Process of Enterobactin

There total 17 articles about Enterobactin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

Hexa-O-benzylenterochelin (88195-64-6) → L-enterobactin (28384-96-5)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; ethyl acetate; for 24h;

DOI:10.1002/anie.201603921

Reference yield:

(3S,7S,11S)-3,7,11-triamino-1,5,9-trioxacyclodecane-2,6,10-trione trihydrochloride (104530-71-4) → L-enterobactin (28384-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: H₂ / Pd/C

With hydrogen; triethylamine; palladium on activated charcoal;

DOI:10.1016/S0040-4039(96)02452-5

Reference yield:

tris(N-trityl-L-serine) trilactone (88109-07-3) → L-enterobactin (28384-96-5)

Guidance literature:

Multi-step reaction with 3 steps

1: HCl / ethanol

2: Et₃N

3: H₂ / Pd/C

With hydrogenchloride; hydrogen; triethylamine; palladium on activated charcoal; In ethanol;

DOI:10.1016/S0040-4039(96)02452-5

upstream raw materials:

Hexa-O-benzylenterochelin

(3S,7S,11S)-3,7,11-triamino-1,5,9-trioxacyclodecane-2,6,10-trione trihydrochloride

tris(N-trityl-L-serine) trilactone

2,3-bis(benzyloxy)benzoyl chloride

Downstream raw materials:

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)

(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)

N,N',N''-tris(2,3-dihydroxybenzoyl)-O-L-seryl-O-L-seryl L-serine

2,3-dihydroxybenzoyl-L-serine

Refernces

• 1、 Shanzer, Abraham,Libman, Jacqueline. "Total Synthesis of Enterobactin via an Organotin Template". . p. 846 - 847. Retrieved 1983.
• 2、 Baramov, Todor,Keijzer, Karlijn,Irran, Elisabeth,Moesker, Eva,Baik, Mu-Hyun,Suessmuth, Roderich. "Synthesis and structural characterization of hexacoordinate silicon, germanium, and titanium complexes of the E. coli siderophore enterobactin". supporting information. p. 10536 - 10542. Retrieved 2013/08/23.