2.0 2012-05-31 14:03:48 -0600 2015-06-03 15:54:41 -0600 ECMDB04056 M2MDB000588 2,3-Dihydrodipicolinic acid L-2,3-Dihydrodipicolinate is involved in the lysine biosynthesis pathway. L-2,3-Dihydrodipicolinate is produced from a reaction between pyruvate and L-aspartate-semialdehyde, with water as a byproduct. The reaction is catalyzed by dihydrodipicolinate synthase. 2,3-Di-H-Dipicolinate 2,3-Di-H-Dipicolinic acid 2,3-Dihydrodipicolinate 2,3-DPA Dihydrodipicolinate Dihydrodipicolinic acid L-2,3-Dihydrodipicolinate L-2,3-Dihydrodipicolinic acid C7H7NO4 169.1348 169.037507717 2,3-dihydropyridine-2,6-dicarboxylic acid 2,3-dihydrodipicolinic acid 16052-12-3 OC(=O)C1CC=CC(=N1)C(O)=O InChI=1S/C7H7NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-2,5H,3H2,(H,9,10)(H,11,12) UWOCFOFVIBZJGH-UHFFFAOYSA-N Solid Cytosol logp 0.12 ALOGPS logs -1.39 ALOGPS solubility 6.84e+00 g/l ALOGPS melting_point 135.2 logp 0.66 ChemAxon pka_strongest_acidic 3.17 ChemAxon pka_strongest_basic -1.1 ChemAxon iupac 2,3-dihydropyridine-2,6-dicarboxylic acid ChemAxon average_mass 169.1348 ChemAxon mono_mass 169.037507717 ChemAxon smiles OC(=O)C1CC=CC(=N1)C(O)=O ChemAxon formula C7H7NO4 ChemAxon inchi InChI=1S/C7H7NO4/c9-6(10)4-2-1-3-5(8-4)7(11)12/h1-2,5H,3H2,(H,9,10)(H,11,12) ChemAxon inchikey UWOCFOFVIBZJGH-UHFFFAOYSA-N ChemAxon polar_surface_area 86.96 ChemAxon refractivity 39.36 ChemAxon polarizability 15.08 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 5 ChemAxon donor_count 2 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 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 lysine biosynthesis I DAPLYSINESYN-PWY Specdb::CMs 14882 Specdb::CMs 39883 Specdb::CMs 164885 Specdb::NmrOneD 96598 Specdb::NmrOneD 96599 Specdb::NmrOneD 96600 Specdb::NmrOneD 96601 Specdb::NmrOneD 96602 Specdb::NmrOneD 96603 Specdb::NmrOneD 96604 Specdb::NmrOneD 96605 Specdb::NmrOneD 96606 Specdb::NmrOneD 96607 Specdb::NmrOneD 96608 Specdb::NmrOneD 96609 Specdb::NmrOneD 96610 Specdb::NmrOneD 96611 Specdb::NmrOneD 96612 Specdb::NmrOneD 96613 Specdb::NmrOneD 96614 Specdb::NmrOneD 96615 Specdb::NmrOneD 96616 Specdb::NmrOneD 96617 Specdb::MsMs 32003 Specdb::MsMs 32004 Specdb::MsMs 32005 Specdb::MsMs 2443606 Specdb::MsMs 2443607 Specdb::MsMs 2443608 Specdb::MsMs 25445 Specdb::MsMs 25446 Specdb::MsMs 25447 Specdb::MsMs 2521989 Specdb::MsMs 2521990 Specdb::MsMs 2521991 HMDB12247 17 16 C03340 30620 2-3-DIHYDRODIPICOLINATE 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 Dihydrodipicolinate reductase P04036 DAPB_ECOLI dapB http://ecmdb.ca/proteins/P04036.xml Dihydrodipicolinate synthase P0A6L2 DAPA_ECOLI dapA http://ecmdb.ca/proteins/P0A6L2.xml Uncharacterized protein yjhH P39359 YJHH_ECOLI yjhH http://ecmdb.ca/proteins/P39359.xml Uncharacterized protein yagE P75682 YAGE_ECOLI yagE http://ecmdb.ca/proteins/P75682.xml 2,3-Dihydrodipicolinic acid + Hydrogen ion + NADPH > NADP + Tetrahydrodipicolinate R04199 L-Aspartate-semialdehyde + Pyruvic acid > 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water R02292 DIHYDRODIPICSYN-RXN L-Aspartate-semialdehyde + Pyruvic acid <> 2,3-Dihydrodipicolinic acid +2 Water R02292 Tetrahydrodipicolinate + NAD <> 2,3-Dihydrodipicolinic acid + NADH + Hydrogen ion R04198 Tetrahydrodipicolinate + NADP <> 2,3-Dihydrodipicolinic acid + NADPH + Hydrogen ion R04199 Pyruvic acid + L-Aspartate-semialdehyde <> Hydrogen ion + Water + 2,3-Dihydrodipicolinic acid DIHYDRODIPICSYN-RXN NAD(P)⁺ + Tetrahydrodipicolinate < NAD(P)H + 2,3-Dihydrodipicolinic acid + Hydrogen ion DIHYDROPICRED-RXN L-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water 2 2,3-Dihydrodipicolinic acid + Hydrogen ion + NADPH > NADP + Tetrahydrodipicolinate L-Aspartate-semialdehyde + Pyruvic acid >2 2,3-Dihydrodipicolinic acid + Hydrogen ion +2 Water