2.02012-08-09 09:16:11 -06002015-09-13 15:15:32 -0600ECMDB21419M2MDB0018142-Phosphoglyceric acid2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia)2-(dihydrogen phosphate)Glycerate2-(dihydrogen phosphate)Glyceric acid2-(Dihydrogen phosphoric acid)glyceric acid2-P-D-Glycerate2-P-D-glyceric acid2-P-glycerate2-P-glyceric acid2-Phospho-(D)-glycerate2-phospho-(D)-Glyceric acid2-Phospho-(R)-glycerate2-phospho-(R)-Glyceric acid2-Phospho-D-glycerate2-Phospho-D-glyceric acid2-phospho-DL-Glycerate2-Phospho-DL-glyceric acid2-Phosphoglycerate3-Hydroxy-2-phosphonooxypropanoate3-Hydroxy-2-phosphonooxypropanoic acidD-2-Phosphoglycerate D-2-Phosphoglyceric acid D-Glycerate 2-phosphateD-Glyceric acid 2-phosphoric acidDL-2-PhosphoglycerateDL-2-Phosphoglyceric acidGlycerate 2-phosphateGlyceric acid 2-phosphateGlyceric acid 2-phosphoric acidPhosphoglyceratePhosphoglyceric acidC3H7O7P186.0572185.992939093-hydroxy-2-(phosphonooxy)propanoic acid2-phosphoglyceric acid2553-59-5OCC(OP(O)(O)=O)C(O)=OInChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)GXIURPTVHJPJLF-UHFFFAOYSA-NSolidCytoplasmlogp-2.24logs-0.96solubility2.03e+01 g/llogp-1.6pka_strongest_acidic0.81pka_strongest_basic-3.1iupac3-hydroxy-2-(phosphonooxy)propanoic acidaverage_mass186.0572mono_mass185.99293909smilesOCC(OP(O)(O)=O)C(O)=OformulaC3H7O7PinchiInChI=1S/C3H7O7P/c4-1-2(3(5)6)10-11(7,8)9/h2,4H,1H2,(H,5,6)(H2,7,8,9)inchikeyGXIURPTVHJPJLF-UHFFFAOYSA-Npolar_surface_area124.29refractivity31.26polarizability13.37rotatable_bond_count4acceptor_count6donor_count4physiological_charge-3formal_charge0Gluconeogenesis from L-malic acidGluconeogenesis from L-malic acid starts from the introduction of L-malic acid into cytoplasm either through a C4 dicarboxylate / orotate:H+ symporter or a dicarboxylate transporter (succinic acid antiporter). L-malic acid is then metabolized through 3 possible ways: NAD driven malate dehydrogenase resulting in oxalacetic acid, NADP driven malate dehydrogenase B resulting pyruvic acid or malate dehydrogenase, NAD-requiring resulting in pyruvic acid.
Oxalacetic acid is processed by phosphoenolpyruvate carboxykinase (ATP driven) while pyruvic acid is processed by phosphoenolpyruvate synthetase resulting in phosphoenolpyruvic acid. This compound is dehydrated by enolase resulting in an 2-phosphoglyceric acid. This compound is then isomerized by 2,3-bisphosphoglycerate-independent phosphoglycerate mutase resulting in a 3-phosphoglyceric acid which is phosphorylated by an ATP driven phosphoglycerate kinase resulting in an glyceric acid 1,3-biphosphate. This compound undergoes an NADH driven glyceraldehyde 3-phosphate dehydrogenase reaction resulting in a D-Glyceraldehyde 3-phosphate which is first isomerized into dihydroxyacetone phosphate through an triosephosphate isomerase. D-glyceraldehyde 3-phosphate and Dihydroxyacetone phosphate react through a fructose biphosphate aldolase protein complex resulting in a fructose 1,6-biphosphate. This compound is metabolized by a fructose-1,6-bisphosphatase resulting in a Beta-D-fructofuranose 6-phosphate which is then isomerized into a Beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase.
PW000819Metabolicsuperpathway of D-glucarate and D-galactarate degradation
Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth.
The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--).
The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde.
Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA.
The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid.
The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid.PW000795MetabolicSpecdb::CMs16065Specdb::CMs37465Specdb::CMs132761Specdb::CMs140495Specdb::CMs1059474Specdb::CMs1059476Specdb::CMs1059478Specdb::CMs1059480Specdb::CMs1059481Specdb::CMs1059483Specdb::CMs1059485Specdb::CMs1059486Specdb::CMs1059488Specdb::CMs1059490Specdb::CMs1059492Specdb::CMs1059494Specdb::CMs1059495Specdb::NmrOneD143670Specdb::NmrOneD143671Specdb::NmrOneD143672Specdb::NmrOneD143673Specdb::NmrOneD143674Specdb::NmrOneD143675Specdb::NmrOneD143676Specdb::NmrOneD143677Specdb::NmrOneD143678Specdb::NmrOneD143679Specdb::NmrOneD143680Specdb::NmrOneD143681Specdb::NmrOneD143682Specdb::NmrOneD143683Specdb::NmrOneD143684Specdb::NmrOneD143685Specdb::NmrOneD143686Specdb::NmrOneD143687Specdb::NmrOneD143688Specdb::NmrOneD143689Specdb::MsMs10028Specdb::MsMs10029Specdb::MsMs10030Specdb::MsMs16700Specdb::MsMs16701Specdb::MsMs16702Specdb::MsMs2228781Specdb::MsMs2230647Specdb::MsMs2231109Specdb::MsMs2233115Specdb::MsMs2233498Specdb::MsMs2235419Specdb::MsMs2289168Specdb::MsMs2289169Specdb::MsMs2289170Specdb::MsMs2650052Specdb::MsMs2650053Specdb::MsMs2650054HMDB003625958243442-Phosphoglyceratevan 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 370:17-25.17765195Winder, 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 80:2939-2948.18331064Reed, G. H., Poyner, R. R., Larsen, T. M., Wedekind, J. E., Rayment, I. (1996). "Structural and mechanistic studies of enolase." Curr Opin Struct Biol 6:736-743.8994873Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18.15882454Fujii H: [Red cell glycolytic intermediates] Nippon Rinsho. 1995 Mar;53 Su Pt 2:234-8.8753225Wang Y, Wei Z, Liu L, Cheng Z, Lin Y, Ji F, Gong W: Crystal structure of human B-type phosphoglycerate mutase bound with citrate. Biochem Biophys Res Commun. 2005 Jun 17;331(4):1207-15.15883004Comi GP, Fortunato F, Lucchiari S, Bordoni A, Prelle A, Jann S, Keller A, Ciscato P, Galbiati S, Chiveri L, Torrente Y, Scarlato G, Bresolin N: Beta-enolase deficiency, a new metabolic myopathy of distal glycolysis. Ann Neurol. 2001 Aug;50(2):202-7.11506403Hakobyan D, Nazaryan K: Investigation of interaction between enolase and phosphoglycerate mutase using molecular dynamics simulation. J Biomol Struct Dyn. 2006 Jun;23(6):625-34.16615808Tsujino S, Shanske S, Sakoda S, Toscano A, DiMauro S: Molecular genetic studies in muscle phosphoglycerate mutase (PGAM-M) deficiency. Muscle Nerve. 1995;3:S50-3.7603528Mulquiney PJ, Bubb WA, Kuchel PW: Model of 2,3-bisphosphoglycerate metabolism in the human erythrocyte based on detailed enzyme kinetic equations: in vivo kinetic characterization of 2,3-bisphosphoglycerate synthase/phosphatase using 13C and 31P NMR. Biochem J. 1999 Sep 15;342 Pt 3:567-80.10477268Reher M, Bott M, Schonheit P: Characterization of glycerate kinase (2-phosphoglycerate forming), a key enzyme of the nonphosphorylative Entner-Doudoroff pathway, from the thermoacidophilic euryarchaeon Picrophilus torridus. FEMS Microbiol Lett. 2006 Jun;259(1):113-9.16684110Wold, Finn. L-Glyceric acid monophosphates. Journal of Organic Chemistry (1961), 26 197-9. EnolaseP0A6P9ENO_ECOLIenohttp://ecmdb.ca/proteins/P0A6P9.xmlGlycerate kinase 2P23524GLXK2_ECOLIgarKhttp://ecmdb.ca/proteins/P23524.xml2,3-bisphosphoglycerate-independent phosphoglycerate mutaseP37689GPMI_ECOLIgpmIhttp://ecmdb.ca/proteins/P37689.xml2-Phosphoglyceric acid + 2-Phosphoglyceric acid > 3-Phosphoglyceric acid + 3-PhosphoglyceratePW_R002933Phosphoenolpyruvic acid > Water + 2-Phosphoglyceric acid + 2-Phosphoglyceric acidPW_R0029322-Phosphoglyceric acid + 2-Phosphoglyceric acid <> Water + Phosphoenolpyruvic acidPW_R003674Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acidPW_R002728