2.02012-05-31 13:57:38 -06002015-09-13 12:56:12 -0600ECMDB03035M2MDB000475Glycolic acidGlycolic 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-Hydroxyacetate2-Hydroxyacetic acidA-HydroxyacetateA-Hydroxyacetic acidAlpha-HydroxyacetateAlpha-Hydroxyacetic acidGlycocideGlycolateGlycolic acidGlycollateGlycollic acidGlyPureGlyPure 70HydroxyacetateHydroxyacetic acidHydroxyethanoateHydroxyethanoic acidSodium glycolateSodium glycolic acidα-Hydroxyacetateα-Hydroxyacetic acidC2H4O376.051476.0160439942-hydroxyacetic acidglycolic acid79-14-1OCC(O)=OInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)AEMRFAOFKBGASW-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp-1.02logs0.90solubility6.08e+02 g/lmelting_point75-80 oClogp-1pka_strongest_acidic3.53pka_strongest_basic-3.6iupac2-hydroxyacetic acidaverage_mass76.0514mono_mass76.016043994smilesOCC(O)=OformulaC2H4O3inchiInChI=1S/C2H4O3/c3-1-2(4)5/h3H,1H2,(H,4,5)inchikeyAEMRFAOFKBGASW-UHFFFAOYSA-Npolar_surface_area57.53refractivity14.35polarizability6.2rotatable_bond_count1acceptor_count3donor_count2physiological_charge-1formal_charge0gamma-Hexachlorocyclohexane degradationec00361Glyoxylate and dicarboxylate metabolismec00630Microbial metabolism in diverse environmentsec01120Chloroalkane and chloroalkene degradationec00625glycolate 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.
PW000827Metabolicinner membrane transportlist 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 addedPW000786MetabolicD-arabinose degradation IE. 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)PW002038MetabolicEthylene Glycol DegradationAlthough 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)PW002093Metabolicglycolate and glyoxylate degradation IGLYCOLATEMET-PWYsuperpathway of glycol metabolism and degradationGLYOXDEG-PWYethylene glycol degradationPWY0-1280D-arabinose degradation IDARABCATK12-PWYSpecdb::CMs331Specdb::CMs332Specdb::CMs910Specdb::CMs3449Specdb::CMs29929Specdb::CMs29930Specdb::CMs30129Specdb::CMs30560Specdb::CMs30870Specdb::CMs31002Specdb::CMs31970Specdb::CMs37300Specdb::CMs131943Specdb::CMs139677Specdb::CMs1050341Specdb::CMs1050342Specdb::CMs1050344Specdb::CMs1050346Specdb::CMs1050347Specdb::EiMs611Specdb::NmrOneD1089Specdb::NmrOneD2650Specdb::NmrOneD3336Specdb::NmrOneD4969Specdb::NmrOneD4970Specdb::NmrOneD5752Specdb::NmrOneD5753Specdb::NmrOneD5754Specdb::NmrOneD5755Specdb::NmrOneD5756Specdb::NmrOneD5757Specdb::NmrOneD5758Specdb::NmrOneD5759Specdb::NmrOneD5760Specdb::NmrOneD5761Specdb::NmrOneD5762Specdb::NmrOneD5763Specdb::NmrOneD5764Specdb::NmrOneD5765Specdb::NmrOneD5766Specdb::NmrOneD5767Specdb::NmrOneD5768Specdb::NmrOneD5769Specdb::NmrOneD5770Specdb::NmrOneD5771Specdb::MsMs165Specdb::MsMs166Specdb::MsMs167Specdb::MsMs2898Specdb::MsMs2899Specdb::MsMs2900Specdb::MsMs11648Specdb::MsMs11649Specdb::MsMs11650Specdb::MsMs18320Specdb::MsMs18321Specdb::MsMs18322Specdb::MsMs437680Specdb::MsMs437681Specdb::MsMs437682Specdb::MsMs1474283Specdb::MsMs1474284Specdb::MsMs1474285Specdb::MsMs1474286Specdb::MsMs1474287Specdb::MsMs1474288Specdb::MsMs1474289Specdb::MsMs1474290Specdb::MsMs1474291Specdb::MsMs1474292Specdb::NmrTwoD1147HMDB00115757737C0354729805GLYCOLLATEGOAGlycolic acidKeseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510van 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). 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Xenobiotica. 2004 Jan;34(1):31-48.14742135Horikoshi T, Matsumoto M, Usuki A, Igarashi S, Hikima R, Uchiwa H, Hayashi S, Brysk MM, Ichihashi M, Funasaka Y: Effects of glycolic acid on desquamation-regulating proteinases in human stratum corneum. Exp Dermatol. 2005 Jan;14(1):34-40.15660917DiNardo JC, Grove GL, Moy LS: Clinical and histological effects of glycolic acid at different concentrations and pH levels. Dermatol Surg. 1996 May;22(5):421-4.8634803Marangella M, Petrarulo M, Bianco O, Vitale C, Finocchiaro P, Linari F: Glycolate determination detects type I primary hyperoxaluria in dialysis patients. Kidney Int. 1991 Jan;39(1):149-54.2002628Tsiafoulis CG, Prodromidis MI, Karayannis MI: Development of amperometric biosensors for the determination of glycolic acid in real samples. Anal Chem. 2002 Jan 1;74(1):132-9.11795781Porter WH, Rutter PW, Yao HH: Simultaneous determination of ethylene glycol and glycolic acid in serum by gas chromatography-mass spectrometry. 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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?1358894437Glycolate oxidase subunit glcDP0AEP9GLCD_ECOLIglcDhttp://ecmdb.ca/proteins/P0AEP9.xmlLactaldehyde dehydrogenaseP25553ALDA_ECOLIaldAhttp://ecmdb.ca/proteins/P25553.xmlPhosphoglycolate phosphataseP32662GPH_ECOLIgphhttp://ecmdb.ca/proteins/P32662.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.xmlGlycolate oxidase subunit glcEP52073GLCE_ECOLIglcEhttp://ecmdb.ca/proteins/P52073.xmlCation/acetate symporter ActPP32705ACTP_ECOLIactPhttp://ecmdb.ca/proteins/P32705.xmlL-lactate permeaseP33231LLDP_ECOLIlldPhttp://ecmdb.ca/proteins/P33231.xmlGlycolate permease glcAQ46839GLCA_ECOLIglcAhttp://ecmdb.ca/proteins/Q46839.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.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 + NADGlycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADHR01333GLYCOLALD-DEHYDROG-RXNPhosphoglycolic acid + Water <> Glycolic acid + Phosphate + GlycolateR01334GPH-RXNGlycolic acid + NADP <> Glyoxylic acid + NADPH + Hydrogen ionR00465GLYOXYLATE-REDUCTASE-NADP+-RXNGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideR00475Glycolaldehyde + NAD + Water <> Glycolic acid + NADH + Hydrogen ionR01333GLYCOLALD-DEHYDROG-RXNPhosphoglycolic acid + Water <> Glycolic acid + PhosphateR01334Water + NAD + Glycolaldehyde > Hydrogen ion + NADH + Glycolic acidGLYCOLALD-DEHYDROG-RXNan oxidized electron acceptor + Glycolic acid > a reduced electron acceptor + Glyoxylic acidGLYCOLATEDEHYDRO-RXNGlycolic acid + NADP < Hydrogen ion + NADPH + Glyoxylic acidGLYOXYLATE-REDUCTASE-NADP+-RXNWater + Phosphoglycolic acid > Glycolic acid + PhosphateR01334GPH-RXNGlycolaldehyde + NAD + Water > Glycolic acid + NADHGlycolic acid + NADP > Glyoxylic acid + NADPHPhosphoglycolic acid + Water > Glycolic acid + Inorganic phosphateGlycolic 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 + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADPGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideGlyoxylic acid + Hydrogen ion + NADPH + Glycolate <> Glycolic acid + NADPGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxideGlycolic acid + Oxygen <> Glyoxylic acid + Hydrogen peroxide