2.02012-05-31 13:55:54 -06002015-09-13 12:56:12 -0600ECMDB02165M2MDB000444GlycolaldehydeGlycolaldehyde (HOCH2-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). Glycolaldehyde is readily converted to acetyl coenzyme A. It has an aldehyde and a hydroxyl group. However, it is not actually a sugar, because there is only one hydroxyl group. Glycolaldehyde is formed from many sources, including the amino acid glycine and from purone catabolism. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamin pyrophosphate during the pentose phosphate shunt.2-Hydroxyacetaldehyde2-Hydroxyethanal2-OH-acetaldehyde2-OxoethanolDioseGlycoaldehydeGlycolaldehydeGlycolic aldehydeGlycollaldehydeHydroxyacetaldehydeHydroxyethanalMethylol formaldehydeMethylolformaldehydeMonomethylolformaldehydeC2H4O260.05260.0211293722-hydroxyacetaldehydeglycolaldehyde141-46-8OCC=OInChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2WGCNASOHLSPBMP-UHFFFAOYSA-NSolidCytosollogp-0.99logs1.08solubility7.25e+02 g/lmelting_point97 oClogp-1.2pka_strongest_acidic14.27pka_strongest_basic-3.1iupac2-hydroxyacetaldehydeaverage_mass60.052mono_mass60.021129372smilesOCC=OformulaC2H4O2inchiInChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2inchikeyWGCNASOHLSPBMP-UHFFFAOYSA-Npolar_surface_area37.3refractivity13.42polarizability5.32rotatable_bond_count1acceptor_count2donor_count1physiological_charge0formal_charge0Folate biosynthesisThe biosynthesis of folic acid begins with a product of purine nucleotides de novo biosynthesis pathway, GTP. This compound is involved in a reaction with water through a GTP cyclohydrolase 1 protein complex, resulting in a hydrogen ion, formic acid and 7,8-dihydroneopterin 3-triphosphate. The latter compound is dephosphatased through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, hydrogen ion and 7,8-dihydroneopterin 3-phosphate. The latter compound reacts with water spontaneously resulting in the release of a phosphate and a 7,8 -dihydroneopterin. This compound reacts with a dihydroneopterin aldolase, releasing a glycoaldehyde and 6-hydroxymethyl-7,9-dihydropterin. The latter compound is phosphorylated with a ATP-driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in a (2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate.
Chorismate is metabolized by reacting with L-glutamine through a 4-amino-4-deoxychorismate synthase resulting in L-glutamic acid and 4-amino-4-deoxychorismate. The latter compound then reacts through an aminodeoxychorismate lyase resulting in pyruvic acid,hydrogen ion and p-aminobenzoic acid.
(2-amino-4-hydroxy-7,8-dihydropteridin-6-yl)methyl diphosphate and p-aminobenzoic acid react through a dihydropteroate synthase resulting in pyrophosphate and 7,8-dihydropteroic acid. This compound reacts with L-glutamic acid through an ATP driven bifunctional folylpolyglutamate synthetase / dihydrofolate synthetase resulting in a 7,8-dihydrofolate monoglutamate. This compound is reduced through an NADPH mediated dihydrofolate reductase resulting in a tetrahydrofate.
This product goes on to a one carbon pool by folate pathway.
PW000908ec00790MetabolicVitamin B6 metabolismec00750Pentose and glucuronate interconversionsec00040Glyoxylate and dicarboxylate metabolismec00630Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100GTP degradationGTP, produced in the nucleotide de novo biosyntheis pathway, interacts with a water molecule through a GTP cyclohydrolase resulting in a formate, hydrogen ion and a 7,8-dihydroneopterin 3'-triphosphate. The latter compound interacts with a water molecule through a dihydroneopterin triphosphate pyrophosphohydrolase resulting in the release of a pyrophosphate, a hydrogen ion and a 7,8-dihydroneopterin 3'-phosphate. The latter compound interacts with water spontaneously resulting in the release of a phosphate and a 7,8 dihydroneopterin. The latter compound interacts with a dihydroneopterin aldolase resulting in the release of a glycolaldehyde and a 6-hydroxymethyl-7,8-dihydropterin. This compound then is then diphosphorylated by reacting with a ATP driven 6-hydroxymethyl-7,8-dihydropterin pyrophosphokinase resulting in the release of a hydrogen ion, an AMP and 6-hydroxymethyl-7,8-dihydropterin diphosphate.
GTP interacts with a cyclic pyranopterin monophosphate synthase resulting in the release of a diphosphate and a cyclic pyranopterin phosphate. The latter compound interacts with a thiocarboxylated small subunit of molybdopterin synthase (a protein) and a water molecule through a molybdopterin synthase resulting in the release of 4 hydrogen ions, 2 small subunits of molybdopterin synthase and a molybdopterin. The molybdopterin interacts with an ATP and a hydrogen ion through a molybdopterin adenylyltransferase resulting in the release of a diphosphate and a molybdopterin adenine dinucleotide.PW001888MetabolicD-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)PW002093Metabolic6-hydroxymethyl-dihydropterin diphosphate biosynthesis IPWY-6147ethylene glycol degradationPWY0-1280D-arabinose degradation IDARABCATK12-PWYSpecdb::CMs3440Specdb::CMs38577Specdb::CMs161573Specdb::EiMs1733Specdb::NmrOneD4851Specdb::NmrOneD4852Specdb::NmrOneD135670Specdb::NmrOneD135671Specdb::NmrOneD135672Specdb::NmrOneD135673Specdb::NmrOneD135674Specdb::NmrOneD135675Specdb::NmrOneD135676Specdb::NmrOneD135677Specdb::NmrOneD135678Specdb::NmrOneD135679Specdb::NmrOneD135680Specdb::NmrOneD135681Specdb::NmrOneD135682Specdb::NmrOneD135683Specdb::NmrOneD135684Specdb::NmrOneD135685Specdb::NmrOneD135686Specdb::NmrOneD135687Specdb::NmrOneD135688Specdb::NmrOneD135689Specdb::MsMs21080Specdb::MsMs21081Specdb::MsMs21082Specdb::MsMs22631Specdb::MsMs22632Specdb::MsMs22633Specdb::MsMs1470894Specdb::MsMs1470895Specdb::MsMs1470896Specdb::MsMs2243993Specdb::MsMs2246082Specdb::MsMs2248114Specdb::MsMs2382359Specdb::MsMs2382360Specdb::MsMs2382361Specdb::MsMs2579940Specdb::MsMs2579941Specdb::MsMs2579942HMDB03344756736C0026617071GLYCOLALDEHYDEGlycolaldehydeKeseler, 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). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948.18331064Choei H, Sasaki N, Takeuchi M, Yoshida T, Ukai W, Yamagishi S, Kikuchi S, Saito T: Glyceraldehyde-derived advanced glycation end products in Alzheimer's disease. Acta Neuropathol (Berl). 2004 Sep;108(3):189-93. Epub 2004 Jun 17.15221334Takeuchi M, Yamagishi S: TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses. 2004;63(3):449-52.15288366Majerski, Piotr A.; Piskorz, Jan K.; Radlein, Desmond St. A. G. Production of glycolaldehyde by hydrous thermolysis of sugars. PCT Int. Appl. (2002), 41 pp.http://hmdb.ca/system/metabolites/msds/000/002/925/original/HMDB03344.pdf?1358461902Lactaldehyde reductaseP0A9S1FUCO_ECOLIfucOhttp://ecmdb.ca/proteins/P0A9S1.xmlL-fuculose phosphate aldolaseP0AB87FUCA_ECOLIfucAhttp://ecmdb.ca/proteins/P0AB87.xmlDihydroneopterin aldolaseP0AC16FOLB_ECOLIfolBhttp://ecmdb.ca/proteins/P0AC16.xmlLactaldehyde dehydrogenaseP25553ALDA_ECOLIaldAhttp://ecmdb.ca/proteins/P25553.xmlRhamnulose-1-phosphate aldolaseP32169RHAD_ECOLIrhaDhttp://ecmdb.ca/proteins/P32169.xmlAlkanesulfonate monooxygenaseP80645SSUD_ECOLIssuDhttp://ecmdb.ca/proteins/P80645.xmlFMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + SulfiteRXN-13418Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADHR01333GLYCOLALD-DEHYDROG-RXN7,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + GlycolaldehydeR03504H2NEOPTERINALDOL-RXNGlycolaldehyde + NAD + Water <> Glycolic acid + NADH + Hydrogen ionR01333GLYCOLALD-DEHYDROG-RXNEthylene glycol + NAD <> Glycolaldehyde + NADH + Hydrogen ionR01781L-Xylulose 1-phosphate <> Dihydroxyacetone phosphate + GlycolaldehydeR01785D-Ribulose-1-phosphate <> Glycolaldehyde + Dihydroxyacetone phosphateDARABALDOL-RXNWater + NAD + Glycolaldehyde > Hydrogen ion + NADH + Glycolic acidGLYCOLALD-DEHYDROG-RXN7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterinH2NEOPTERINALDOL-RXN4-Hydroxy-L-threonine <> Glycolaldehyde + GlycineRXN0-6563Glycolaldehyde + NAD + Water > Glycolic acid + NADH2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine > 6-Hydroxymethyl dihydropterin + Glycolaldehyde7,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterinPW_R003399D-Ribulose-1-phosphate <> Glycolaldehyde + Glycerone phosphatePW_R0059567 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde