2.02015-06-04 15:15:06 -06002015-09-17 15:41:57 -0600ECMDB23778M2MDB004261(2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinateThe 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 acidC7H7NO5185.136185.033519489(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 acidOC1CC(N=C(C1)C([O-])=O)C([O-])=OInChI=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-2DVTPRYHENFBCII-UHFFFAOYSA-Llogp-1.06logs-1.15solubility1.33e+01 g/llogp-0.64pka_strongest_acidic3.13pka_strongest_basic-2.3iupac(2S,4S)-4-hydroxy-2,3,4,5-tetrahydropyridine-2,6-dicarboxylic acidaverage_mass185.136mono_mass185.033519489smilesOC1CC(N=C(C1)C([O-])=O)C([O-])=OformulaC7H7NO5inchiInChI=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-2inchikeyDVTPRYHENFBCII-UHFFFAOYSA-Lpolar_surface_area107.19refractivity39.74polarizability16.67rotatable_bond_count2acceptor_count6donor_count3physiological_charge-2formal_charge0Lysine biosynthesisLysine 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.PW000771ec00300MetabolicMicrobial metabolism in diverse environmentsec01120Monobactam biosynthesiseco00261Metabolic pathwayseco01100Specdb::MsMs25982Specdb::MsMs25983Specdb::MsMs25984Specdb::MsMs32540Specdb::MsMs32541Specdb::MsMs32542C20258Dihydrodipicolinate reductaseP04036DAPB_ECOLIdapBhttp://ecmdb.ca/proteins/P04036.xmlDihydrodipicolinate synthaseP0A6L2DAPA_ECOLIdapAhttp://ecmdb.ca/proteins/P0A6L2.xmlUncharacterized protein yjhHP39359YJHH_ECOLIyjhHhttp://ecmdb.ca/proteins/P39359.xmlUncharacterized protein yagEP75682YAGE_ECOLIyagEhttp://ecmdb.ca/proteins/P75682.xmlTetrahydrodipicolinate + NAD + NADP + Water <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + NADH + NADPH + Hydrogen ionR04198 R04199 Pyruvic acid + L-Aspartate-semialdehyde <> (2S,4S)-4-Hydroxy-2,3,4,5-tetrahydrodipicolinate + WaterR10147 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-tetrahydrodipicolinatePW_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-tetrahydrodipicolinatePW_R002528