2.0 2012-05-31 14:04:17 -0600 2015-09-13 12:56:13 -0600 ECMDB04077 M2MDB000597 Glyceric acid Glyceric acid is a colorless syrupy acid, obtained from oxidation of glycerol. It is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Several phosphate derivatives of glyceric acid, including 2-phosphoglyceric acid, 3-phosphoglyceric acid, 2,3-bisphosphoglyceric acid, and 1,3-bisphosphoglyceric acid, are important biochemical intermediates. (Wikipedia) (R)-glycerate (R)-glyceric acid D-glycerate A,b-Hydroxypropionate A,b-Hydroxypropionic acid Alpha,beta-Hydroxypropionate Alpha,beta-Hydroxypropionic acid D-Glycerate D-Glyceric acid Glycerate Glyceric acid α,β-Hydroxypropionate α,β-Hydroxypropionic acid C3H6O4 106.0773 106.02660868 (2R)-2,3-dihydroxypropanoic acid glycerate 473-81-4 OC[C@@H](O)C(O)=O InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1 RBNPOMFGQQGHHO-UWTATZPHSA-N Liquid Cytosol Extra-organism Periplasm logp -1.72 ALOGPS logs 0.78 ALOGPS solubility 6.39e+02 g/l ALOGPS logp -1.5 ChemAxon pka_strongest_acidic 3.42 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2R)-2,3-dihydroxypropanoic acid ChemAxon average_mass 106.0773 ChemAxon mono_mass 106.02660868 ChemAxon smiles OC[C@@H](O)C(O)=O ChemAxon formula C3H6O4 ChemAxon inchi InChI=1S/C3H6O4/c4-1-2(5)3(6)7/h2,4-5H,1H2,(H,6,7)/t2-/m1/s1 ChemAxon inchikey RBNPOMFGQQGHHO-UWTATZPHSA-N ChemAxon polar_surface_area 77.76 ChemAxon refractivity 20.38 ChemAxon polarizability 8.96 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Pentose phosphate pathway ec00030 Glycine, serine and threonine metabolism ec00260 Methane metabolism ec00680 Glyoxylate and dicarboxylate metabolism ec00630 Glycerolipid metabolism ec00561 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 glycolate and glyoxylate degradation Glycolic 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. PW000827 Metabolic superpathway 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. PW000795 Metabolic glycolate and glyoxylate degradation II Oxaloglycolate (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. PW002021 Metabolic 2-O-alpha-mannosyl-D-glycerate degradation 2-O-α-Mannosyl-D-glycerate (MG) is an osmolyte utilized by hyperthermophilic archaea and bacteria. E. coli is able to utilize MG as a carbon source but not as protection against osmotic stress. MG utilization is controlled by the divergently transcribed mngR gene and mngAB operon. MngR acts as a repressor of the expression both mngR and mngAB. MngA is the EII of a PEP-dependent sugar phosphotransferase system responsible for the uptake and phosphorylation of MG to 2-O-(6-phospho-α-mannosyl)-D-glycerate, which is subsequently converted to mannose-6-phosphate and glycerate by the α-mannosidase MngB. Glycerate can be converted to 2-phosphoglycerate by glycerate kinase I encoded by the garK gene which is also induced when cells are grown in MG. (EcoCyc) PW002096 Metabolic glycolate and glyoxylate degradation I GLYCOLATEMET-PWY D-galactarate degradation I GALACTARDEG-PWY D-glucarate degradation I GLUCARDEG-PWY 2-O-α-mannosyl-D-glycerate degradation PWY0-1300 Specdb::CMs 365 Specdb::CMs 1050 Specdb::CMs 2550 Specdb::CMs 30159 Specdb::CMs 30556 Specdb::CMs 31018 Specdb::CMs 37316 Specdb::CMs 130558 Specdb::CMs 138292 Specdb::CMs 1051423 Specdb::CMs 1051425 Specdb::CMs 1051427 Specdb::CMs 1051428 Specdb::CMs 1051430 Specdb::CMs 1051432 Specdb::CMs 1051434 Specdb::CMs 1051435 Specdb::CMs 1051437 Specdb::CMs 1051439 Specdb::CMs 1051441 Specdb::CMs 1051442 Specdb::CMs 1051444 Specdb::NmrOneD 1106 Specdb::NmrOneD 142490 Specdb::NmrOneD 142491 Specdb::NmrOneD 142492 Specdb::NmrOneD 142493 Specdb::NmrOneD 142494 Specdb::NmrOneD 142495 Specdb::NmrOneD 142496 Specdb::NmrOneD 142497 Specdb::NmrOneD 142498 Specdb::NmrOneD 142499 Specdb::NmrOneD 142500 Specdb::NmrOneD 142501 Specdb::NmrOneD 142502 Specdb::NmrOneD 142503 Specdb::NmrOneD 142504 Specdb::NmrOneD 142505 Specdb::NmrOneD 142506 Specdb::NmrOneD 142507 Specdb::NmrOneD 142508 Specdb::NmrOneD 142509 Specdb::MsMs 212 Specdb::MsMs 213 Specdb::MsMs 214 Specdb::MsMs 3047 Specdb::MsMs 3048 Specdb::MsMs 3049 Specdb::MsMs 3050 Specdb::MsMs 3051 Specdb::MsMs 3053 Specdb::MsMs 178419 Specdb::MsMs 178420 Specdb::MsMs 178421 Specdb::MsMs 180738 Specdb::MsMs 180739 Specdb::MsMs 180740 Specdb::MsMs 437706 Specdb::MsMs 437707 Specdb::MsMs 437708 Specdb::MsMs 437709 Specdb::MsMs 437710 Specdb::MsMs 439228 Specdb::MsMs 2226409 Specdb::MsMs 2231137 Specdb::MsMs 2233082 Specdb::MsMs 2233454 Specdb::NmrTwoD 1164 HMDB00139 439194 388334 C00258 16659 GLYCERATE DGY Glyceric acid Keseler, I. 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Journal of Organic Chemistry (1987), 52(11), 2318-19. http://hmdb.ca/system/metabolites/msds/000/000/096/original/HMDB00139.pdf?1358462162 2-hydroxy-3-oxopropionate reductase P0ABQ2 GARR_ECOLI garR http://ecmdb.ca/proteins/P0ABQ2.xml Glycerate kinase 2 P23524 GLXK2_ECOLI garK http://ecmdb.ca/proteins/P23524.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml Glyoxylate/hydroxypyruvate reductase A P75913 GHRA_ECOLI ghrA http://ecmdb.ca/proteins/P75913.xml D-malate dehydrogenase [decarboxylating] P76251 DMLA_ECOLI dmlA http://ecmdb.ca/proteins/P76251.xml 2-hydroxy-3-oxopropionate reductase_ P77161 GLXR_ECOLI glxR http://ecmdb.ca/proteins/P77161.xml Glycerate kinase 1 P77364 GLXK1_ECOLI glxK http://ecmdb.ca/proteins/P77364.xml Alpha-mannosidase mngB P54746 MNGB_ECOLI mngB http://ecmdb.ca/proteins/P54746.xml Probable glucarate transporter Q46916 GUDP_ECOLI gudP http://ecmdb.ca/proteins/Q46916.xml Probable galactarate transporter P0AA80 GARP_ECOLI garP http://ecmdb.ca/proteins/P0AA80.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD R01745 RXN0-5289 Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD R01388 Hydrogen ion + Hydroxypyruvic acid + NADPH > Glyceric acid + NADP R01392 RXN0-300 Adenosine triphosphate + Glyceric acid > 3-Phosphoglycerate + ADP + Hydrogen ion GLY3KIN-RXN Water + 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate > Glyceric acid + Mannose 6-phosphate RXN0-5216 Adenosine triphosphate + Glyceric acid > 2-Phospho-D-glyceric acid + ADP + Hydrogen ion GKI-RXN Glyceric acid + NAD <> Hydroxypyruvic acid + NADH + Hydrogen ion R01388 Glyceric acid + NADP <> Hydroxypyruvic acid + NADPH + Hydrogen ion R01392 Adenosine triphosphate + Glyceric acid <> ADP + 3-Phospho-D-glycerate R01514 Glyceric acid + NAD <> Tartronate semialdehyde + NADH + Hydrogen ion R01745 RXN0-5289 Glyceric acid + NADP <> Tartronate semialdehyde + NADPH + Hydrogen ion R01747 Tartaric acid <> Glyceric acid + Carbon dioxide R01751 NAD(P)+ + Glyceric acid < NAD(P)H + Tartronate semialdehyde + Hydrogen ion TSA-REDUCT-RXN Glyceric acid + NAD(P)(+) > Tartronate semialdehyde + NAD(P)H Glyceric acid + NAD(P)(+) > Hydroxypyruvic acid + NAD(P)H Adenosine triphosphate + Glyceric acid > ADP + 2-Phospho-D-glyceric acid Adenosine triphosphate + Glyceric acid > ADP + 3-Phospho-D-glycerate R01514 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid Glyceric acid + NAD + NADP <> Tartronate semialdehyde + NADH + NADPH + Hydrogen ion R01745 R01747 2(alpha-D-Mannosyl-6-phosphate)-D-glycerate + Water <> Mannose 6-phosphate + Glyceric acid R09645 Tartronate semialdehyde + Hydrogen ion + NADPH + NADPH > NADP + Glyceric acid PW_R002727 Glyceric acid + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + 2-Phosphoglyceric acid + ADP + 2-Phosphoglyceric acid PW_R002728 Glyceric acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + 3-Phosphoglyceric acid + ADP + 3-Phosphoglycerate PW_R002984 Tartronate semialdehyde + NADH + Hydrogen ion > NAD + Glyceric acid PW_R002983 2-O-(6-Phospho-alpha-D-mannosyl)-D-glycerate + Water > Mannose 6-phosphate + Glyceric acid PW_R006116 Adenosine triphosphate + Glyceric acid <> ADP +3 3-Phospho-D-glycerate Adenosine triphosphate + Glyceric acid > ADP +3 3-Phospho-D-glycerate Tartronate semialdehyde + Hydrogen ion + NADH <> Glyceric acid + NAD Hydrogen ion + Hydroxypyruvic acid + NADH > Glyceric acid + NAD Adenosine triphosphate + Glyceric acid <> ADP +3 3-Phospho-D-glycerate Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucose Shake flask and filter culture 1410.0 uM 0.0 37 oC K12 NCM3722 Mid-Log Phase 5640000 0 Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. 19561621