2.02012-05-31 09:57:38 -06002015-09-13 12:56:06 -0600ECMDB00119M2MDB000043Glyoxylic acidGlyoxylic acid or oxoacetic acid is an organic compound that is both an aldehyde and a carboxylic acid. It is an intermediate of the glyoxylate cycle, which enables certain organisms to convert fatty acids into carbohydrates.The conjugate base of gloxylic acid is known as glyoxylate. This compound is an intermediate of the glyoxylate cycle, which enables organisms, such as bacteria, fungi and plants to convert fatty acids into carbohydrates. Glyoxylate is the byproduct of the amidation process in biosynthesis of several amidated peptides. The glyoxylate cycle is a metabolic pathway occurring in plants, and several microorganisms, such as E. coli and yeast. (PMID: 16396466)A-KetoacetateA-Ketoacetic acidAlpha-KetoacetateAlpha-Ketoacetic acidFormylformateFormylformic acidGlyoxGlyoxalateGlyoxalic acidGlyoxylateGlyoxylic acidOxalaldehydateOxalaldehydic acidOxoacetateOxoacetic acidOxoethanoateOxoethanoic acidα-Ketoacetateα-Ketoacetic acidC2H2O374.035574.000393932-oxoacetic acidglyoxylic acid298-12-4OC(=O)C=OInChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)HHLFWLYXYJOTON-UHFFFAOYSA-NLiquidCytosollogp-0.59logs0.48solubility2.24e+02 g/lmelting_point-93 oClogp-0.13pka_strongest_acidic2.61pka_strongest_basic-9.2iupac2-oxoacetic acidaverage_mass74.0355mono_mass74.00039393smilesOC(=O)C=OformulaC2H2O3inchiInChI=1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)inchikeyHHLFWLYXYJOTON-UHFFFAOYSA-Npolar_surface_area54.37refractivity13.5polarizability5.35rotatable_bond_count1acceptor_count3donor_count1physiological_charge-1formal_charge0Pentose phosphate pathwayec00030Arginine and proline metabolismec00330Purine metabolismec00230Glycine, serine and threonine metabolismec00260Pyruvate metabolismec00620Methane metabolismec00680C5-Branched dibasic acid metabolismec00660Glyoxylate and dicarboxylate metabolismec00630Microbial metabolism in diverse environmentsec01120Chloroalkane and chloroalkene degradationec00625Metabolic pathwayseco01100Secondary Metabolites: Glyoxylate cycleThe glyoxylate cycle starts with the interaction of Acetyl-Coa with a water molecule and Oxalacetic acid interact through a Citrate synthase resulting in a release of a coenzyme a and citric acid. The citric acid gets dehydrated through a citrate hydro-lyase resulting in the release of a water molecule and cis-Aconitic acid. The cis-Aconitic acid is then hydrated in an reversible reaction through an aconitate hydratase resulting in an Isocitric acid. The isocitric acid then interacts in a reversible reaction through isocitrate lyase resulting in the release of a succinic acid and a glyoxylic acid. The glyoxylic acid then reacts in a reversible reaction with an acetyl-coa, and a water molecule in a reversible reaction, resulting in a release of a coenzyme A, a hydrogen ion and an L-malic acid. The L-malic acid interacts in a reversible reaction through a NAD driven malate dehydrogenase resulting in the release of NADH, a hydrogen ion and an Oxalacetic acid.PW000967Metabolicglycolate and glyoxylate degradationGlycolic acid is introduced into the cytoplasm through either a glycolate / lactate:H+ symporter or a acetate / glycolate transporter. Once inside, glycolic acid reacts with an oxidized electron-transfer flavoprotein through a glycolate oxidase resulting in a reduced acceptor and glyoxylic acid. Glyoxylic acid can also be obtained from the introduction of glyoxylic acid. It can also be obtained from the metabolism of (S)-allantoin.
S-allantoin is introduced into the cytoplasm through a purine and pyrimidine transporter(allantoin specific). Once inside, the compound reacts with water through a allantoinase resulting in hydrogen ion and allantoic acid. Allantoic acid then reacts with water and hydrogen ion through a allantoate amidohydrolase resulting in a carbon dioxide, ammonium and S-ureidoglycine. The latter compound reacts with water through a S-ureidoglycine aminohydrolase resulting in ammonium and S-ureidoglycolic acid which in turn reacts with a Ureidoglycolate lyase resulting in urea and glyoxylic acid.
Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle.
Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase.
PW000827Metabolicglycolate and glyoxylate degradation IIOxaloglycolate (2-Hydroxy-3-oxosuccinate) interacts with a tartrate dehydrogenase resulting in a L-tartrate. L-tartrate then interacts with tartrate dehydrogenase resulting in a Oxaloacetate. Oxaloacetate and acetyl-coa interact to result in a citrate which is processed by a aconitate hydratase resulting in a cis-Aconitate and further more into a isocitrate which will eventually be procressed into a glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase.PW002021Metabolicglyoxylate cycleGLYOXYLATE-BYPASSglycolate and glyoxylate degradation IGLYCOLATEMET-PWYsuperpathway of glycol metabolism and degradationGLYOXDEG-PWYallantoin degradation to glyoxylate IIIPWY-5705Specdb::CMs893Specdb::CMs2958Specdb::CMs31004Specdb::CMs37302Specdb::CMs162291Specdb::CMs1050359Specdb::EiMs1251Specdb::NmrOneD1091Specdb::NmrOneD4736Specdb::NmrOneD4737Specdb::NmrOneD142290Specdb::NmrOneD142291Specdb::NmrOneD142292Specdb::NmrOneD142293Specdb::NmrOneD142294Specdb::NmrOneD142295Specdb::NmrOneD142296Specdb::NmrOneD142297Specdb::NmrOneD142298Specdb::NmrOneD142299Specdb::NmrOneD142300Specdb::NmrOneD142301Specdb::NmrOneD142302Specdb::NmrOneD142303Specdb::NmrOneD142304Specdb::NmrOneD142305Specdb::NmrOneD142306Specdb::NmrOneD142307Specdb::NmrOneD142308Specdb::NmrOneD142309Specdb::MsMs171Specdb::MsMs172Specdb::MsMs173Specdb::MsMs2909Specdb::MsMs2910Specdb::MsMs2911Specdb::MsMs11255Specdb::MsMs11256Specdb::MsMs11257Specdb::MsMs17927Specdb::MsMs17928Specdb::MsMs17929Specdb::MsMs437683Specdb::MsMs437684Specdb::MsMs437685Specdb::MsMs2775380Specdb::MsMs2775381Specdb::MsMs2775382Specdb::MsMs2907258Specdb::MsMs2907259Specdb::MsMs2907260Specdb::NmrTwoD1149HMDB00119760740C0004816891GLYOXGLVGlyoxylic acidKeseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 5pp. http://hmdb.ca/system/metabolites/msds/000/000/081/original/HMDB00119.pdf?1358463323Malate synthase AP08997MASY_ECOLIaceBhttp://ecmdb.ca/proteins/P08997.xmlKHG/KDPG aldolaseP0A955ALKH_ECOLIedahttp://ecmdb.ca/proteins/P0A955.xmlIsocitrate lyaseP0A9G6ACEA_ECOLIaceAhttp://ecmdb.ca/proteins/P0A9G6.xmlGlyoxylate carboligaseP0AEP7GCL_ECOLIgclhttp://ecmdb.ca/proteins/P0AEP7.xmlGlycolate oxidase subunit glcDP0AEP9GLCD_ECOLIglcDhttp://ecmdb.ca/proteins/P0AEP9.xmlMalate synthase GP37330MASZ_ECOLIglcBhttp://ecmdb.ca/proteins/P37330.xmlGlyoxylate/hydroxypyruvate reductase BP37666GHRB_ECOLIghrBhttp://ecmdb.ca/proteins/P37666.xmlGlycolate oxidase iron-sulfur subunitP52074GLCF_ECOLIglcFhttp://ecmdb.ca/proteins/P52074.xmlGlyoxylate/hydroxypyruvate reductase AP75913GHRA_ECOLIghrAhttp://ecmdb.ca/proteins/P75913.xmlUreidoglycolate hydrolaseP77731ALLA_ECOLIallAhttp://ecmdb.ca/proteins/P77731.xmlAlkanesulfonate monooxygenaseP80645SSUD_ECOLIssuDhttp://ecmdb.ca/proteins/P80645.xmlGlycolate oxidase subunit glcEP52073GLCE_ECOLIglcEhttp://ecmdb.ca/proteins/P52073.xmlShort-chain fatty acids transporterP76460ATOE_ECOLIatoEhttp://ecmdb.ca/proteins/P76460.xmlGlyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADPR00465GLYOXYLATE-REDUCTASE-NADP+-RXNGlycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 82-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acidGlyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NADAcetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acidR00472MALSYN-RXN2 Hydrogen ion + Water + (S)-Ureidoglycolic acid > Carbon dioxide + Glyoxylic acid +2 Ammonium2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxideR00013GLYOCARBOLIG-RXNFMNH + Oxygen + Sulfoacetate > Flavin Mononucleotide + Glyoxylic acid + Hydrogen ion + Water + SulfiteIsocitric acid <> Glyoxylic acid + Succinic acidR00479ISOCIT-CLEAV-RXN2 Glyoxylic acid <> Tartronate semialdehyde + Carbon dioxideR00013Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ionR00465GLYOXYLATE-REDUCTASE-NADP+-RXN(S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxideR004694-Hydroxy-2-oxoglutaric acid <> Pyruvic acid + Glyoxylic acidR004704OH2OXOGLUTARALDOL-RXND-4-Hydroxy-2-oxoglutarate <> Pyruvic acid + Glyoxylic acidR00471L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acidR00472Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideR00475Dehydroglycine + Water > Glyoxylic acid + AmmoniaRXN-133294-Hydroxy-2-oxoglutaric acid Glyoxylic acid + Pyruvic acid4OH2OXOGLUTARALDOL-RXNan oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acidGLYCOLATEDEHYDRO-RXNHydrogen ion + Glyoxylic acid > Carbon dioxide + Tartronate semialdehydeGLYOCARBOLIG-RXNGlycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acidGLYOXYLATE-REDUCTASE-NADP+-RXNPropionyl-CoA + Water + Glyoxylic acid <> 2-hydroxyglutarate + Hydrogen ion + Coenzyme AHYDGLUTSYN-RXNAcetyl-CoA + Water + Glyoxylic acid > Hydrogen ion + L-Malic acid + Coenzyme AMALSYN-RXN(S)-Ureidoglycolic acid > Urea + Glyoxylic acidUREIDOGLYCOLATE-LYASE-RXNIsocitric acid > Succinic acid + Glyoxylic acid4-Hydroxy-2-oxoglutaric acid > Pyruvic acid + Glyoxylic acid(S)-Ureidoglycolic acid + Water > Glyoxylic acid +2 Ammonia + Carbon dioxide2 Glyoxylic acid > Tartronate semialdehyde + Carbon dioxideGlycolic acid + NADP > Glyoxylic acid + NADPHAcetyl-CoA + Water + Glyoxylic acid > L-Malic acid + CoA(S)-Ureidoglycolic acid <> Glyoxylic acid + UreaR00776 L-Alanine + Glyoxylic acid + L-Alanine <> Glycine + Pyruvic acidPW_R002587Glycolic acid + an oxidized electron-transfer flavoprotein > Reduced acceptor + Glyoxylic acidPW_R0029792 Glycolic acid + 2 an oxidized electron-transfer flavoprotein >2 Reduced acceptor +2 Glyoxylic acidPW_R002981Glyoxylic acid + Water + Acetyl-CoA > Coenzyme A + Hydrogen ion + L-Malic acid + L-Malic acidPW_R0029802 Glyoxylic acid + Hydrogen ion > Carbon dioxide + Tartronate semialdehydePW_R002982Isocitric acid + Isocitric acid <> Succinic acid + Glyoxylic acidPW_R003710Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid2 Glyoxylic acid + Hydrogen ion <> Tartronate semialdehyde + Carbon dioxide(S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxideGlyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADPIsocitric acid <> Glyoxylic acid + Succinic acidGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide(S)-Ureidoglycolic acid + Water <> Glyoxylic acid +2 Ammonia + Carbon dioxideGlyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADPIsocitric acid <> Glyoxylic acid + Succinic acidGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide