2.02012-05-31 14:36:39 -06002015-07-07 10:42:07 -0600ECMDB20274M2MDB001114EthylenediamineEthylenediamine (abbreviated as en when a ligand) is the organic compound with the formula C2H4(NH2)2. This colorless liquid with an ammonia-like odor is a strongly basic amine. It is a widely used building block in chemical synthesis, with approximately 500,000,000 kg being produced in 1998.In terms of quantities produced, ethylenediamine is the most significant diamine (aside from diaminohexane, which is a precursor to Nylon 6-6). Related derivatives of ethylenediamine include tetramethylethylenediamine, abbreviated (TMEDA), (CH3)2N-CH2CH2-N(CH3)2 and tetraethylethylenediamine, abbreviated (TEEDA), (C2H5)2N-CH2CH2-N(C2H5)2The bleaching activator tetraacetylethylenediamine is generated from ethylenediamine. The derivative N,N-ethylenebis(stearamide) (EBS) is a commercially significant mold-release agent and a surfactant in gasoline and motor oil."1,2-Diamino-ethaan1,2-Diamino-ethano1,2-Diaminoaethan1,2-Diaminoethane1,2-Diaminoethane dihydrochloride1,2-Ethanediamine1,2-Ethanediamine, dihydrochloride1,2-Ethylenediamine1,2-ETHYLENEDIAMINE(HYDROCHLORIDE)1,4-Butanediamine1,4-DiaminobutaneAethaldiaminAethylenediaminb-AminoethylamineBeta-AminoethylamineChlor-ethamineDiaminoethaneDimethylenediamineDimethylenediamine dihydrochlorideDimethylenediamine diydrochlorideEthane-1,2-diamineEthanediamineEthyleendiamineEthylendiamineEthylenediamine di HCLEthylenediamine dihydrochlorideEthylenediamine hydrochloride (van)Ethylenediamine, dihydrochlorideEthylenediammonium chlorideEthylenediammonium dichlorideH2NCH2CH2NH2PutrescineTetramethylenediamineβ-AminoethylamineC2H9N261.106361.0765732982-aminoethan-1-aminium2-aminoethanaminium333-18-6NCC[NH3+]InChI=1S/C2H8N2/c3-1-2-4/h1-4H2/p+1PIICEJLVQHRZGT-UHFFFAOYSA-OLiquidCytoplasmPeriplasmlogp-3.01logs0.13solubility1.30e+02 g/lmelting_point 9 °Clogp-1.4pka_strongest_basic9.69iupac2-aminoethan-1-aminiumaverage_mass61.1063mono_mass61.076573298smilesNCC[NH3+]formulaC2H9N2inchiInChI=1S/C2H8N2/c3-1-2-4/h1-4H2/p+1inchikeyPIICEJLVQHRZGT-UHFFFAOYSA-Opolar_surface_area53.66refractivity29.16polarizability7.42rotatable_bond_count1acceptor_count1donor_count2physiological_charge1formal_charge1Glutathione metabolismThe biosynthesis of glutathione starts with the introduction of L-glutamic acid through either a glutamate:sodium symporter, glutamate / aspartate : H+ symporter GltP or a
glutamate / aspartate ABC transporter. Once in the cytoplasm, L-glutamice acid reacts with L-cysteine through an ATP glutamate-cysteine ligase resulting in gamma-glutamylcysteine. This compound reacts which Glycine through an ATP driven glutathione synthetase thus catabolizing Glutathione.
This compound is metabolized through a spontaneous reaction with an oxidized glutaredoxin resulting in a reduced glutaredoxin and an oxidized glutathione. This compound is reduced by a NADPH glutathione reductase resulting in a glutathione.
PW000833ec00480MetabolicArginine and proline metabolismec00330Cysteine and methionine metabolismec00270beta-Alanine metabolismThe Beta-Alanine Metabolism starts with a product of Aspartate metabolism. Aspartate is decarboxylated by aspartate 1-decarboxylase, releasing carbon dioxide and Beta-alanine. Beta alanine is then metabolized through a pantothenate synthetase resulting in Pantothenic acid undergoes phosphorylation through a ATP driven pantothenate kinase, resulting in D-4-phosphopantothenate.
Pantothenate (vitamin B5) is the universal precursor for the synthesis of the 4'-phosphopantetheine moiety of coenzyme A and acyl carrier protein. Only plants and microorganismscan synthesize pantothenate de novo - animals require a dietary supplement. The enzymes of this pathway are therefore considered to be antimicrobial drug targets.PW000896ec00410MetabolicABC transportersec02010Metabolic pathwayseco01100Specdb::NmrOneD331322Specdb::NmrOneD331323Specdb::NmrOneD331324Specdb::NmrOneD331325Specdb::NmrOneD331326Specdb::NmrOneD331327Specdb::NmrOneD331328Specdb::NmrOneD331329Specdb::NmrOneD331330Specdb::NmrOneD331331Specdb::NmrOneD331332Specdb::NmrOneD331333Specdb::NmrOneD331334Specdb::NmrOneD331335Specdb::NmrOneD331336Specdb::NmrOneD331337Specdb::NmrOneD331338Specdb::NmrOneD331339Specdb::NmrOneD331340Specdb::NmrOneD331341Specdb::MsMs27944Specdb::MsMs27945Specdb::MsMs27946Specdb::MsMs34502Specdb::MsMs34503Specdb::MsMs3450450636604240651C0013430347CPD-3682Keseler, 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-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776Spermidine synthaseP09158SPEE_ECOLIspeEhttp://ecmdb.ca/proteins/P09158.xmlSpermidine N(1)-acetyltransferaseP0A951ATDA_ECOLIspeGhttp://ecmdb.ca/proteins/P0A951.xmlOrnithine decarboxylase, constitutiveP21169DCOR_ECOLIspeChttp://ecmdb.ca/proteins/P21169.xmlOrnithine decarboxylase, inducibleP24169DCOS_ECOLIspeFhttp://ecmdb.ca/proteins/P24169.xmlPutrescine aminotransferaseP42588PAT_ECOLIpatAhttp://ecmdb.ca/proteins/P42588.xmlAgmatinaseP60651SPEB_ECOLIspeBhttp://ecmdb.ca/proteins/P60651.xmlGamma-glutamylputrescine synthetaseP78061PUUA_ECOLIpuuAhttp://ecmdb.ca/proteins/P78061.xmlAgmatine + Water <> Putrescine + Urea + EthylenediamineR01157AGMATIN-RXNEthylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + WaterR10064 S-Adenosylmethioninamine + Putrescine + Ethylenediamine <> 5'-Methylthioadenosine + Hydrogen ion + SpermidineR01920SPERMIDINESYN-RXNHydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + EthylenediamineR00670ORNDECARBOX-RXNAdenosine triphosphate + L-Glutamate + Putrescine + Ethylenediamine <> ADP + gamma-Glutamyl-L-putrescine + Hydrogen ion + PhosphateR07414RXN0-3901S-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + SpermidineHydrogen ion + Ornithine + L-Ornithine <> Carbon dioxide + Putrescine + EthylenediamineS-Adenosylmethioninamine + Putrescine + Ethylenediamine <>5 5'-Methylthioadenosine + Hydrogen ion + Spermidine48 mM Na2HPO4, 22 mM KH2PO4, 10 mM NaCl, 45 mM (NH4)2SO4, supplemented with 1 mM MgSO4, 1 mg/l thiamine·HCl, 5.6 mg/l CaCl2, 8 mg/l FeCl3, 1 mg/l MnCl2·4H2O, 1.7 mg/l ZnCl2, 0.43 mg/l CuCl2·2H2O, 0.6 mg/l CoCl2·2H2O and 0.6 mg/l Na2MoO4·2H2O. 4 g/L GlucoBioreactor, pH controlled, O2 and CO2 controlled, dilution rate: 0.2/h69.5uM0.037 oCBW25113Stationary Phase, glucose limited2780000Ishii, N., Nakahigashi, K., Baba, T., Robert, M., Soga, T., Kanai, A., Hirasawa, T., Naba, M., Hirai, K., Hoque, A., Ho, P. Y., Kakazu, Y., Sugawara, K., Igarashi, S., Harada, S., Masuda, T., Sugiyama, N., Togashi, T., Hasegawa, M., Takai, Y., Yugi, K., Arakawa, K., Iwata, N., Toya, Y., Nakayama, Y., Nishioka, T., Shimizu, K., Mori, H., Tomita, M. (2007). "Multiple high-throughput analyses monitor the response of E. coli to perturbations." Science 316:593-597.17379776