2.0 2012-05-31 13:57:38 -0600 2015-09-13 12:56:12 -0600 ECMDB03035 M2MDB000475 Glycolic acid Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid (AHA). In its pure form, glycolic acid is a colorless crystalline solid. Due to its excellent capability to penetrate skin, glycolic acid finds applications in skin care products, most often as a chemical peel. Glycolic acid is also used for tattoo removal. In E coli it is involved in glyoxylate and dicarboxylate metabolism. 2-Hydroxyacetate 2-Hydroxyacetic acid A-Hydroxyacetate A-Hydroxyacetic acid Alpha-Hydroxyacetate Alpha-Hydroxyacetic acid Glycocide Glycolate Glycolic acid Glycollate Glycollic acid GlyPure GlyPure 70 Hydroxyacetate Hydroxyacetic acid Hydroxyethanoate Hydroxyethanoic acid Sodium glycolate Sodium glycolic acid α-Hydroxyacetate α-Hydroxyacetic acid C2H4O3 76.0514 76.016043994 2-hydroxyacetic acid glycolic acid 79-14-1 OCC(O)=O InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) AEMRFAOFKBGASW-UHFFFAOYSA-N Solid Cytosol Extra-organism Periplasm logp -1.02 ALOGPS logs 0.90 ALOGPS solubility 6.08e+02 g/l ALOGPS melting_point 75-80 oC logp -1 ChemAxon pka_strongest_acidic 3.53 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 2-hydroxyacetic acid ChemAxon average_mass 76.0514 ChemAxon mono_mass 76.016043994 ChemAxon smiles OCC(O)=O ChemAxon formula C2H4O3 ChemAxon inchi InChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5) ChemAxon inchikey AEMRFAOFKBGASW-UHFFFAOYSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 14.35 ChemAxon polarizability 6.2 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon gamma-Hexachlorocyclohexane degradation ec00361 Glyoxylate and dicarboxylate metabolism ec00630 Microbial metabolism in diverse environments ec01120 Chloroalkane and chloroalkene degradation ec00625 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 inner membrane transport list of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol This pathway should be updated regularly with the new inner membrae transports added PW000786 Metabolic D-arabinose degradation I E. coli K-12 uses the enzymes of the fucose degradation pathway for utilization of D-arabinose. Expression of the enzymes in this pathway is normally induced by L-fucose and not by D-arabinose; thus, wild-type E. coli K-12 can not use D-arabinose as a sole source of carbon and energy without prior induction by growth on L-fucose. Growth on D-arabinose requires a mutation in the transcriptional regulator FucR. D-arabinose is metabolized yielding dihydroxy-acetone phosphate, an intermediate of glycolysis, which thereby enters central metabolism, and glycolaldehyde. Glycolaldehyde may be further catabolized to glycolate. (EcoCyc) PW002038 Metabolic Ethylene Glycol Degradation Although wild-type E. coli is unable to utilize ethylene glycol as a carbon source, mutant strains can be isolated that can utilize it. Such strains carry two regulatory mutations: one that elevates the levels of propanediol oxidoreductase, the normal function of which is to metabolize propanediol, and the other that elevates the levels of aldehyde reductases, an enzyme of low specificity which participates in the degradation of fucose. (EcoCyc) PW002093 Metabolic glycolate and glyoxylate degradation I GLYCOLATEMET-PWY superpathway of glycol metabolism and degradation GLYOXDEG-PWY ethylene glycol degradation PWY0-1280 D-arabinose degradation I DARABCATK12-PWY Specdb::CMs 331 Specdb::CMs 332 Specdb::CMs 910 Specdb::CMs 3449 Specdb::CMs 29929 Specdb::CMs 29930 Specdb::CMs 30129 Specdb::CMs 30560 Specdb::CMs 30870 Specdb::CMs 31002 Specdb::CMs 31970 Specdb::CMs 37300 Specdb::CMs 131943 Specdb::CMs 139677 Specdb::CMs 1050341 Specdb::CMs 1050342 Specdb::CMs 1050344 Specdb::CMs 1050346 Specdb::CMs 1050347 Specdb::EiMs 611 Specdb::NmrOneD 1089 Specdb::NmrOneD 2650 Specdb::NmrOneD 3336 Specdb::NmrOneD 4969 Specdb::NmrOneD 4970 Specdb::NmrOneD 5752 Specdb::NmrOneD 5753 Specdb::NmrOneD 5754 Specdb::NmrOneD 5755 Specdb::NmrOneD 5756 Specdb::NmrOneD 5757 Specdb::NmrOneD 5758 Specdb::NmrOneD 5759 Specdb::NmrOneD 5760 Specdb::NmrOneD 5761 Specdb::NmrOneD 5762 Specdb::NmrOneD 5763 Specdb::NmrOneD 5764 Specdb::NmrOneD 5765 Specdb::NmrOneD 5766 Specdb::NmrOneD 5767 Specdb::NmrOneD 5768 Specdb::NmrOneD 5769 Specdb::NmrOneD 5770 Specdb::NmrOneD 5771 Specdb::MsMs 165 Specdb::MsMs 166 Specdb::MsMs 167 Specdb::MsMs 2898 Specdb::MsMs 2899 Specdb::MsMs 2900 Specdb::MsMs 11648 Specdb::MsMs 11649 Specdb::MsMs 11650 Specdb::MsMs 18320 Specdb::MsMs 18321 Specdb::MsMs 18322 Specdb::MsMs 437680 Specdb::MsMs 437681 Specdb::MsMs 437682 Specdb::MsMs 1474283 Specdb::MsMs 1474284 Specdb::MsMs 1474285 Specdb::MsMs 1474286 Specdb::MsMs 1474287 Specdb::MsMs 1474288 Specdb::MsMs 1474289 Specdb::MsMs 1474290 Specdb::MsMs 1474291 Specdb::MsMs 1474292 Specdb::NmrTwoD 1147 HMDB00115 757 737 C03547 29805 GLYCOLLATE GOA Glycolic acid Keseler, I. 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Journal of the American Chemical Society (1917), 39 109-12. http://hmdb.ca/system/metabolites/msds/000/000/078/original/HMDB00115.pdf?1358894437 Glycolate oxidase subunit glcD P0AEP9 GLCD_ECOLI glcD http://ecmdb.ca/proteins/P0AEP9.xml Lactaldehyde dehydrogenase P25553 ALDA_ECOLI aldA http://ecmdb.ca/proteins/P25553.xml Phosphoglycolate phosphatase P32662 GPH_ECOLI gph http://ecmdb.ca/proteins/P32662.xml Glyoxylate/hydroxypyruvate reductase B P37666 GHRB_ECOLI ghrB http://ecmdb.ca/proteins/P37666.xml Glycolate oxidase iron-sulfur subunit P52074 GLCF_ECOLI glcF http://ecmdb.ca/proteins/P52074.xml Glyoxylate/hydroxypyruvate reductase A P75913 GHRA_ECOLI ghrA http://ecmdb.ca/proteins/P75913.xml Glycolate oxidase subunit glcE P52073 GLCE_ECOLI glcE http://ecmdb.ca/proteins/P52073.xml Cation/acetate symporter ActP P32705 ACTP_ECOLI actP http://ecmdb.ca/proteins/P32705.xml L-lactate permease P33231 LLDP_ECOLI lldP http://ecmdb.ca/proteins/P33231.xml Glycolate permease glcA Q46839 GLCA_ECOLI glcA http://ecmdb.ca/proteins/Q46839.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 Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP R00465 GLYOXYLATE-REDUCTASE-NADP+-RXN Glycolic acid + Ubiquinone-8 > Glyoxylic acid + Ubiquinol-8 Glycolic acid + Menaquinone 8 > Glyoxylic acid + Menaquinol 8 2-Demethylmenaquinone 8 + Glycolic acid > 2-Demethylmenaquinol 8 + Glyoxylic acid Glyoxylic acid + Hydrogen ion + NADH > Glycolic acid + NAD Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADH R01333 GLYCOLALD-DEHYDROG-RXN Phosphoglycolic acid + Water <> Glycolic acid + Phosphate + Glycolate R01334 GPH-RXN Glycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ion R00465 GLYOXYLATE-REDUCTASE-NADP+-RXN Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide R00475 Glycolaldehyde + NAD + Water <> Glycolic acid + NADH + Hydrogen ion R01333 GLYCOLALD-DEHYDROG-RXN Phosphoglycolic acid + Water <> Glycolic acid + Phosphate R01334 Water + NAD + Glycolaldehyde > Hydrogen ion + NADH + Glycolic acid GLYCOLALD-DEHYDROG-RXN an oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acid GLYCOLATEDEHYDRO-RXN Glycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acid GLYOXYLATE-REDUCTASE-NADP+-RXN Water + Phosphoglycolic acid > Glycolic acid + Phosphate R01334 GPH-RXN Glycolaldehyde + NAD + Water > Glycolic acid + NADH Glycolic acid + NADP > Glyoxylic acid + NADPH Phosphoglycolic acid + Water > Glycolic acid + Inorganic phosphate Glycolic acid + an oxidized electron-transfer flavoprotein  > Reduced acceptor + Glyoxylic acid PW_R002979 2 Glycolic acid + 2 an oxidized electron-transfer flavoprotein  >2 Reduced acceptor +2 Glyoxylic acid PW_R002981 Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADP Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide Glycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide