2.0 2012-05-31 14:21:27 -0600 2015-06-03 17:19:04 -0600 ECMDB12267 M2MDB000836 N-Succinyl-L,L-2,6-diaminopimelate N-Succinyl-L,L-2,6-diaminopimelate is an intermediate in lysine biosynthesis. It is the third to last step in the synthesis of lysine and is converted from N-Succinyl-2-amino-6-ketopimelate via the enzyme succinyldiaminopimelate transferase (EC 2.6.1.17). It is then converted to L,L-diaminopimelate via the enzyme succinyl-diaminopimelate desuccinylase (EC 3.5.1.18). <i>N</i>-succinyl-L-2,6-diaminoheptanedioate <i>N</i>-succinyl-LL-2,6-diaminoheptanedioate L,L-Sdap N-Succinyl-L,L-2,6-diaminopimelic acid N-Succinyl-L-2,6-diaminoheptanedioate N-Succinyl-L-2,6-diaminoheptanedioic acid N-Succinyl-LL-2,6-diaminoheptanedioate N-Succinyl-LL-2,6-diaminoheptanedioic acid N-Succinyl-LL-2,6-diaminopimelate N-Succinyl-LL-2,6-diaminopimelic acid SDPA C11H18N2O7 290.2698 290.11140094 (6S)-2-amino-6-(3-carboxypropanamido)heptanedioic acid (6S)-2-amino-6-(3-carboxypropanamido)heptanedioic acid 26605-36-7 NC(CCC[C@H](NC(=O)CCC(O)=O)C(O)=O)C(O)=O InChI=1S/C11H18N2O7/c12-6(10(17)18)2-1-3-7(11(19)20)13-8(14)4-5-9(15)16/h6-7H,1-5,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t6?,7-/m0/s1 GLXUWZBUPATPBR-MLWJPKLSSA-N Solid Cytosol logp -3.08 ALOGPS logs -1.70 ALOGPS solubility 5.80e+00 g/l ALOGPS logp -3.8 ChemAxon pka_strongest_acidic 1.89 ChemAxon pka_strongest_basic 9.53 ChemAxon iupac (6S)-2-amino-6-(3-carboxypropanamido)heptanedioic acid ChemAxon average_mass 290.2698 ChemAxon mono_mass 290.11140094 ChemAxon smiles NC(CCC[C@H](NC(=O)CCC(O)=O)C(O)=O)C(O)=O ChemAxon formula C11H18N2O7 ChemAxon inchi InChI=1S/C11H18N2O7/c12-6(10(17)18)2-1-3-7(11(19)20)13-8(14)4-5-9(15)16/h6-7H,1-5,12H2,(H,13,14)(H,15,16)(H,17,18)(H,19,20)/t6?,7-/m0/s1 ChemAxon inchikey GLXUWZBUPATPBR-MLWJPKLSSA-N ChemAxon polar_surface_area 167.02 ChemAxon refractivity 63.98 ChemAxon polarizability 27.09 ChemAxon rotatable_bond_count 10 ChemAxon acceptor_count 8 ChemAxon donor_count 5 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon 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 Metabolic pathways eco01100 lysine biosynthesis I DAPLYSINESYN-PWY Specdb::CMs 19444 Specdb::CMs 39890 Specdb::CMs 133566 Specdb::CMs 141300 Specdb::NmrOneD 96838 Specdb::NmrOneD 96839 Specdb::NmrOneD 96840 Specdb::NmrOneD 96841 Specdb::NmrOneD 96842 Specdb::NmrOneD 96843 Specdb::NmrOneD 96844 Specdb::NmrOneD 96845 Specdb::NmrOneD 96846 Specdb::NmrOneD 96847 Specdb::NmrOneD 96848 Specdb::NmrOneD 96849 Specdb::NmrOneD 96850 Specdb::NmrOneD 96851 Specdb::NmrOneD 96852 Specdb::NmrOneD 96853 Specdb::NmrOneD 96854 Specdb::NmrOneD 96855 Specdb::NmrOneD 96856 Specdb::NmrOneD 96857 Specdb::MsMs 27317 Specdb::MsMs 27318 Specdb::MsMs 27319 Specdb::MsMs 33875 Specdb::MsMs 33876 Specdb::MsMs 33877 Specdb::MsMs 2671161 Specdb::MsMs 2671162 Specdb::MsMs 2671163 Specdb::MsMs 3011076 Specdb::MsMs 3011077 Specdb::MsMs 3011078 HMDB12267 25202447 C04421 N-SUCCINYLLL-2-6-DIAMINOPIMELATE 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 Succinyl-diaminopimelate desuccinylase P0AED7 DAPE_ECOLI dapE http://ecmdb.ca/proteins/P0AED7.xml Acetylornithine/succinyldiaminopimelate aminotransferase P18335 ARGD_ECOLI argD http://ecmdb.ca/proteins/P18335.xml Water + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acid R02734 SUCCDIAMINOPIMDESUCC-RXN alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate R04475 Oxoglutaric acid + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate SUCCINYLDIAMINOPIMTRANS-RXN N-Succinyl-2-amino-6-ketopimelate + L-Glutamic acid + L-Glutamate > N-Succinyl-L,L-2,6-diaminopimelate + Oxoglutaric acid PW_R002530 N-Succinyl-L,L-2,6-diaminopimelate + Water > Succinic acid + Diaminopimelic acid PW_R002531 alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate Water + N-Succinyl-L,L-2,6-diaminopimelate <> Diaminopimelic acid + Succinic acid