2.0 2012-05-31 14:21:21 -0600 2015-06-03 17:19:04 -0600 ECMDB12250 M2MDB000834 L-Aspartyl-4-phosphate L-Aspartyl-4-phosphate is involved in both the lysine biosynthesis and homoserine biosynthesis pathways. 4-Phospho-L-aspartate 4-Phospho-L-aspartic acid Asp-P L-&beta;-aspartyl-P L-&beta;-aspartyl-phosphate L-&beta;-aspartyl-phosphoric acid L-4-Aspartyl phosphate L-4-Aspartyl phosphoric acid L-Aspartate b-semialdehyde L-Aspartate beta-semialdehyde L-Aspartate β-semialdehyde L-Aspartic acid b-semialdehyde L-Aspartic acid beta-semialdehyde L-Aspartic acid β-semialdehyde L-aspartyl-&beta;-phosphate L-Aspartyl-&beta;-phosphoric acid L-aspartyl-4-P L-Aspartyl-4-phosphoric acid L-aspartyl-b-phosphate L-Aspartyl-b-phosphoric acid L-Aspartyl-beta-phosphate L-Aspartyl-beta-phosphoric acid L-Aspartyl-β-phosphate L-Aspartyl-β-phosphoric acid L-b-aspartyl-P L-b-aspartyl-phosphate L-b-Aspartyl-phosphoric acid L-beta-Aspartyl-P L-beta-Aspartyl-phosphate L-beta-Aspartyl-phosphoric acid L-β-Aspartyl-P L-β-Aspartyl-phosphate L-β-Aspartyl-phosphoric acid C4H8NO7P 213.0826 213.003838127 2-amino-4-oxo-4-(phosphonooxy)butanoic acid aspartyl phosphate 22138-53-0 NC(CC(=O)OP(O)(O)=O)C(O)=O InChI=1S/C4H8NO7P/c5-2(4(7)8)1-3(6)12-13(9,10)11/h2H,1,5H2,(H,7,8)(H2,9,10,11) IXZNKTPIYKDIGG-UHFFFAOYSA-N Solid Cytosol logp -1.91 ALOGPS logs -1.21 ALOGPS solubility 1.32e+01 g/l ALOGPS logp -3.4 ChemAxon pka_strongest_acidic 1.08 ChemAxon pka_strongest_basic 8.6 ChemAxon iupac 2-amino-4-oxo-4-(phosphonooxy)butanoic acid ChemAxon average_mass 213.0826 ChemAxon mono_mass 213.003838127 ChemAxon smiles NC(CC(=O)OP(O)(O)=O)C(O)=O ChemAxon formula C4H8NO7P ChemAxon inchi InChI=1S/C4H8NO7P/c5-2(4(7)8)1-3(6)12-13(9,10)11/h2H,1,5H2,(H,7,8)(H2,9,10,11) ChemAxon inchikey IXZNKTPIYKDIGG-UHFFFAOYSA-N ChemAxon polar_surface_area 147.15 ChemAxon refractivity 37.69 ChemAxon polarizability 16.08 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 4 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Cysteine and methionine metabolism ec00270 Glycine, serine and threonine metabolism ec00260 Lysine biosynthesis Lysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter , glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis). L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine. L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3. A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid. PW000771 ec00300 Metabolic Microbial metabolism in diverse environments ec01120 Monobactam biosynthesis eco00261 Metabolic pathways eco01100 Secondary Metabolites: threonine biosynthesis from aspartate The biosynthesis of threonine starts with L-aspartic acid being phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000976 Metabolic threonine biosynthesis The biosynthesis of threonine starts with oxalacetic acid interacting with an L-glutamic acid through an aspartate aminotransferase resulting in a oxoglutaric acid and an L-aspartic acid. The latter compound is then phosphorylated by an ATP driven Aspartate kinase resulting in an a release of an ADP and an L-aspartyl-4-phosphate. This compound interacts with a hydrogen ion through an NADPH driven aspartate semialdehyde dehydrogenase resulting in the release of a phosphate, an NADP and a L-aspartate-semialdehyde.The latter compound interacts with a hydrogen ion through a NADPH driven aspartate kinase / homoserine dehydrogenase resulting in the release of an NADP and a L-homoserine. L-homoserine is phosphorylated through an ATP driven homoserine kinase resulting in the release of an ADP, a hydrogen ion and a O-phosphohomoserine. The latter compound then interacts with a water molecule threonine synthase resulting in the release of a phosphate and an L-threonine. PW000817 Metabolic lysine biosynthesis I DAPLYSINESYN-PWY homoserine biosynthesis HOMOSERSYN-PWY Specdb::CMs 19030 Specdb::CMs 39885 Specdb::NmrOneD 324572 Specdb::NmrOneD 324573 Specdb::NmrOneD 324574 Specdb::NmrOneD 324575 Specdb::NmrOneD 324576 Specdb::NmrOneD 324577 Specdb::NmrOneD 324578 Specdb::NmrOneD 324579 Specdb::NmrOneD 324580 Specdb::NmrOneD 324581 Specdb::NmrOneD 324582 Specdb::NmrOneD 324583 Specdb::NmrOneD 324584 Specdb::NmrOneD 324585 Specdb::NmrOneD 324586 Specdb::NmrOneD 324587 Specdb::NmrOneD 324588 Specdb::NmrOneD 324589 Specdb::NmrOneD 324590 Specdb::NmrOneD 324591 Specdb::MsMs 27674 Specdb::MsMs 27675 Specdb::MsMs 27676 Specdb::MsMs 34232 Specdb::MsMs 34233 Specdb::MsMs 34234 HMDB12250 832 809 C03082 L-BETA-ASPARTYL-P Keseler, 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. 21097882 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Bifunctional aspartokinase/homoserine dehydrogenase 1 P00561 AK1H_ECOLI thrA http://ecmdb.ca/proteins/P00561.xml Bifunctional aspartokinase/homoserine dehydrogenase 2 P00562 AK2H_ECOLI metL http://ecmdb.ca/proteins/P00562.xml Lysine-sensitive aspartokinase 3 P08660 AK3_ECOLI lysC http://ecmdb.ca/proteins/P08660.xml Aspartate-semialdehyde dehydrogenase P0A9Q9 DHAS_ECOLI asd http://ecmdb.ca/proteins/P0A9Q9.xml L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-4-phosphate + ADP R00480 ASPARTATEKIN-RXN L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH R02291 ASPARTATE-SEMIALDEHYDE-DEHYDROGENASE-RXN L-Aspartic acid + Adenosine triphosphate > L-Aspartyl-4-phosphate + ADP ASPARTATEKIN-RXN L-Aspartic acid + Adenosine triphosphate + L-Aspartic acid > Adenosine diphosphate + L-Aspartyl-4-phosphate + ADP PW_R002525 L-Aspartyl-4-phosphate + NADPH + Hydrogen ion + NADPH > Phosphate + NADP + L-Aspartate-semialdehyde PW_R002526 L-Aspartic acid + Adenosine triphosphate <> L-Aspartyl-4-phosphate + ADP L-Aspartate-semialdehyde + NADP + Phosphate <> L-Aspartyl-4-phosphate + Hydrogen ion + NADPH