2.02012-07-30 14:54:58 -06002015-06-03 17:20:54 -0600ECMDB21212M2MDB001620EnterochelinEnterobactin (also known as Enterochelin) is a high affinity siderophore that acquires iron for microbial systems. It is primarily found in Gram-negative bacteria, such as Escherichia coli and Salmonella typhimurium.(3S-(3R*,7R*,11R*))-N,N',N''-(2,6,10-trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl)tris(2,3-dihydroxybenzamide)EnterobactinEnterochelinH6entN,N',N''-[(3S,7S,11S)-2,6,10-Trioxo-1,5,9-trioxacyclododecane-3,7,11-triyl]tris(2,3-dihydroxybenzamide)Tri-(2,3-dihydroxy-N-benzoyl-L-serine)-esterTri-(N-(2,3-dihydroxybenzoyl)-L-serine)-esterC30H27N3O15669.5465669.144217209N-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamideenterobactin28384-96-5OC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1OInChI=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/s1SERBHKJMVBATSJ-BZSNNMDCSA-NCytosolExtra-organismMembranePeriplasmlogp1.62logs-3.82solubility1.00e-01 g/llogp2.26pka_strongest_acidic7.82pka_strongest_basic-6.3iupacN-[(3S,7S,11S)-7,11-bis(2,3-dihydroxybenzamido)-2,6,10-trioxo-1,5,9-trioxacyclododecan-3-yl]-2,3-dihydroxybenzamideaverage_mass669.5465mono_mass669.144217209smilesOC1=CC=CC(C(=O)N[C@H]2COC(=O)[C@H](COC(=O)[C@H](COC2=O)NC(=O)C2=CC=CC(O)=C2O)NC(=O)C2=CC=CC(O)=C2O)=C1OformulaC30H27N3O15inchiInChI=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/s1inchikeySERBHKJMVBATSJ-BZSNNMDCSA-Npolar_surface_area287.58refractivity157.87polarizability61.87rotatable_bond_count6acceptor_count12donor_count9physiological_charge0formal_charge0Enterobactin BiosynthesisEnterobactin is a catecholate siderophore produced almost exclusively by enterobacteria, although it has been reported in some Streptomyces species. It is a cyclic compound made of three units of 2,3-dihydroxybenzoylserine joined in a cyclic structure by lactone linkages (only the δ-cis isomer of the ferric chelate is biologically active). Not only the cyclic molecule, but also the biosynthetic precursor 2,3-dihydroxy-N-benzoylserine and its linear dimer and trimer condensation products are able to transport iron into enterobacteria.
Enterobactin is synthesized under iron-deficient conditions and excreted into the environment where it binds Fe(III) with high affinity and specificity. The ferrisiderophore complexes are taken up into the cell by specific transport components. Enterobactin synthesis is divided into two parts: 1) the conversion of chorismate to 2,3-dihydroxybenzoate 2) the synthesis of enterobactin from 2,3-dihydroxybenzoate and L-serine. (EcoCyc)PW002048Metabolicenterobactin biosynthesisENTBACSYN-PWYSpecdb::CMs21119Specdb::CMs701671Specdb::CMs701672Specdb::CMs701673Specdb::CMs701674Specdb::CMs701675Specdb::CMs701676Specdb::CMs701677Specdb::CMs701678Specdb::CMs701679Specdb::CMs701680Specdb::CMs701681Specdb::CMs701682Specdb::CMs701683Specdb::CMs701684Specdb::CMs701685Specdb::CMs701686Specdb::CMs701687Specdb::CMs701688Specdb::CMs701689Specdb::CMs701690Specdb::CMs701691Specdb::CMs701692Specdb::CMs701693Specdb::CMs701694Specdb::MsMs26417Specdb::MsMs26418Specdb::MsMs26419Specdb::MsMs32975Specdb::MsMs32976Specdb::MsMs32977Specdb::MsMs2697390Specdb::MsMs2697391Specdb::MsMs2697392Specdb::MsMs2982059Specdb::MsMs2982060Specdb::MsMs29820613423131543C0582128855ENTEROBACTINEB4EnterochelinKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25.17765195Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Enterobactin synthase component FP11454ENTF_ECOLIentFhttp://ecmdb.ca/proteins/P11454.xmlEnterochelin esteraseP13039FES_ECOLIfeshttp://ecmdb.ca/proteins/P13039.xml4'-phosphopantetheinyl transferase entDP19925ENTD_ECOLIentDhttp://ecmdb.ca/proteins/P19925.xmlEnterobactin exporter entSP24077ENTS_ECOLIentShttp://ecmdb.ca/proteins/P24077.xmlOuter membrane protein tolCP02930TOLC_ECOLItolChttp://ecmdb.ca/proteins/P02930.xml3 (2,3-Dihydroxybenzoyl)adenylic acid + 3 L-Seryl-AMP >6 Adenosine monophosphate + Enterochelin +9 Hydrogen ionENTG-RXNEnterochelin + 3 Water >3 2,3-Dihydroxybenzoylserine +3 Hydrogen ionRXN0-1661Enterochelin + Fe3+ > Ferric enterobactin(2,3-Dihydroxybenzoyl)adenylic acid + L-Seryl-AMP <> Hydrogen ion + Enterochelin + Adenosine monophosphateENTG-RXNEnterochelin + Water > Hydrogen ion + 2,3-DihydroxybenzoylserineRXN0-1661Adenosine triphosphate + L-Serine + 2-Pyrocatechuic acid > Hydrogen ion + Pyrophosphate + Adenosine monophosphate + EnterochelinENTMULTI-RXN3 a DHB-seryl-[EntF peptidyl-carrier protein] > Enterochelin +3 a holo-[EntF peptidyl-carrier protein]PW_R005982