2.0 2015-06-04 15:15:06 -0600 2015-09-17 15:41:57 -0600 ECMDB23778 M2MDB004261 (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate The dicarboxylic acid dianion formed from (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid by proton loss from both carboxy groups; major species present at pH 7.3 (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinic acid (4S)-4-Hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinate (4S)-4-Hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid C7H7NO5 185.136 185.033519489 (2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid (2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid OC1CC(N=C(C1)C([O-])=O)C([O-])=O InChI=1S/C7H9NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h3-4,9H,1-2H2,(H,10,11)(H,12,13)/p-2 DVTPRYHENFBCII-UHFFFAOYSA-L logp -1.06 ALOGPS logs -1.15 ALOGPS solubility 1.33e+01 g/l ALOGPS logp -0.64 ChemAxon pka_strongest_acidic 3.13 ChemAxon pka_strongest_basic -2.3 ChemAxon iupac (2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acid ChemAxon average_mass 185.136 ChemAxon mono_mass 185.033519489 ChemAxon smiles OC1CC(N=C(C1)C([O-])=O)C([O-])=O ChemAxon formula C7H7NO5 ChemAxon inchi InChI=1S/C7H9NO5/c9-3-1-4(6(10)11)8-5(2-3)7(12)13/h3-4,9H,1-2H2,(H,10,11)(H,12,13)/p-2 ChemAxon inchikey DVTPRYHENFBCII-UHFFFAOYSA-L ChemAxon polar_surface_area 107.19 ChemAxon refractivity 39.74 ChemAxon polarizability 16.67 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 6 ChemAxon donor_count 3 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 Monobactam biosynthesis eco00261 Metabolic pathways eco01100 Specdb::MsMs 25982 Specdb::MsMs 25983 Specdb::MsMs 25984 Specdb::MsMs 32540 Specdb::MsMs 32541 Specdb::MsMs 32542 C20258 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 Tetrahydrodipicolinate + NAD + NADP + Water <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADH + NADPH + Hydrogen ion R04198 R04199 Pyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + Water R10147 L-Aspartate-semialdehyde + Pyruvic acid > Hydrogen ion + Water + (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate PW_R002527 (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + Hydrogen ion + NADPH + (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADPH > Water + NADP + (S)-2,3,4,5-tetrahydrodipicolinate PW_R002528