2.0 2012-05-31 13:55:54 -0600 2015-09-13 12:56:12 -0600 ECMDB02165 M2MDB000444 Glycolaldehyde Glycolaldehyde (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-Hydroxyacetaldehyde 2-Hydroxyethanal 2-OH-acetaldehyde 2-Oxoethanol Diose Glycoaldehyde Glycolaldehyde Glycolic aldehyde Glycollaldehyde Hydroxyacetaldehyde Hydroxyethanal Methylol formaldehyde Methylolformaldehyde Monomethylolformaldehyde C2H4O2 60.052 60.021129372 2-hydroxyacetaldehyde glycolaldehyde 141-46-8 OCC=O InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 WGCNASOHLSPBMP-UHFFFAOYSA-N Solid Cytosol logp -0.99 ALOGPS logs 1.08 ALOGPS solubility 7.25e+02 g/l ALOGPS melting_point 97 oC logp -1.2 ChemAxon pka_strongest_acidic 14.27 ChemAxon pka_strongest_basic -3.1 ChemAxon iupac 2-hydroxyacetaldehyde ChemAxon average_mass 60.052 ChemAxon mono_mass 60.021129372 ChemAxon smiles OCC=O ChemAxon formula C2H4O2 ChemAxon inchi InChI=1S/C2H4O2/c3-1-2-4/h1,4H,2H2 ChemAxon inchikey WGCNASOHLSPBMP-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 13.42 ChemAxon polarizability 5.32 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Folate biosynthesis The 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. PW000908 ec00790 Metabolic Vitamin B6 metabolism ec00750 Pentose and glucuronate interconversions ec00040 Glyoxylate and dicarboxylate metabolism ec00630 Microbial metabolism in diverse environments ec01120 Metabolic pathways eco01100 GTP degradation GTP, 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. PW001888 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 6-hydroxymethyl-dihydropterin diphosphate biosynthesis I PWY-6147 ethylene glycol degradation PWY0-1280 D-arabinose degradation I DARABCATK12-PWY Specdb::CMs 3440 Specdb::CMs 38577 Specdb::CMs 161573 Specdb::EiMs 1733 Specdb::NmrOneD 4851 Specdb::NmrOneD 4852 Specdb::NmrOneD 135670 Specdb::NmrOneD 135671 Specdb::NmrOneD 135672 Specdb::NmrOneD 135673 Specdb::NmrOneD 135674 Specdb::NmrOneD 135675 Specdb::NmrOneD 135676 Specdb::NmrOneD 135677 Specdb::NmrOneD 135678 Specdb::NmrOneD 135679 Specdb::NmrOneD 135680 Specdb::NmrOneD 135681 Specdb::NmrOneD 135682 Specdb::NmrOneD 135683 Specdb::NmrOneD 135684 Specdb::NmrOneD 135685 Specdb::NmrOneD 135686 Specdb::NmrOneD 135687 Specdb::NmrOneD 135688 Specdb::NmrOneD 135689 Specdb::MsMs 21080 Specdb::MsMs 21081 Specdb::MsMs 21082 Specdb::MsMs 22631 Specdb::MsMs 22632 Specdb::MsMs 22633 Specdb::MsMs 1470894 Specdb::MsMs 1470895 Specdb::MsMs 1470896 Specdb::MsMs 2243993 Specdb::MsMs 2246082 Specdb::MsMs 2248114 Specdb::MsMs 2382359 Specdb::MsMs 2382360 Specdb::MsMs 2382361 Specdb::MsMs 2579940 Specdb::MsMs 2579941 Specdb::MsMs 2579942 HMDB03344 756 736 C00266 17071 GLYCOLALDEHYDE Glycolaldehyde Keseler, 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. 21097882 Kanehisa, 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. 22080510 van 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. 17765195 Winder, 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. 18331064 Choei 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. 15221334 Takeuchi M, Yamagishi S: TAGE (toxic AGEs) hypothesis in various chronic diseases. Med Hypotheses. 2004;63(3):449-52. 15288366 Majerski, 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?1358461902 Lactaldehyde reductase P0A9S1 FUCO_ECOLI fucO http://ecmdb.ca/proteins/P0A9S1.xml L-fuculose phosphate aldolase P0AB87 FUCA_ECOLI fucA http://ecmdb.ca/proteins/P0AB87.xml Dihydroneopterin aldolase P0AC16 FOLB_ECOLI folB http://ecmdb.ca/proteins/P0AC16.xml Lactaldehyde dehydrogenase P25553 ALDA_ECOLI aldA http://ecmdb.ca/proteins/P25553.xml Rhamnulose-1-phosphate aldolase P32169 RHAD_ECOLI rhaD http://ecmdb.ca/proteins/P32169.xml Alkanesulfonate monooxygenase P80645 SSUD_ECOLI ssuD http://ecmdb.ca/proteins/P80645.xml FMNH + Isethionic acid + Oxygen > Flavin Mononucleotide + Glycolaldehyde + Hydrogen ion + Water + Sulfite RXN-13418 Glycolaldehyde + Water + NAD > Glycolic acid +2 Hydrogen ion + NADH R01333 GLYCOLALD-DEHYDROG-RXN 7,8-Dihydroneopterin <> 6-Hydroxymethyl dihydropterin + Glycolaldehyde R03504 H2NEOPTERINALDOL-RXN Glycolaldehyde + NAD + Water <> Glycolic acid + NADH + Hydrogen ion R01333 GLYCOLALD-DEHYDROG-RXN Ethylene glycol + NAD <> Glycolaldehyde + NADH + Hydrogen ion R01781 L-Xylulose 1-phosphate <> Dihydroxyacetone phosphate + Glycolaldehyde R01785 D-Ribulose-1-phosphate <> Glycolaldehyde + Dihydroxyacetone phosphate DARABALDOL-RXN Water + NAD + Glycolaldehyde > Hydrogen ion + NADH + Glycolic acid GLYCOLALD-DEHYDROG-RXN 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin H2NEOPTERINALDOL-RXN 4-Hydroxy-L-threonine <> Glycolaldehyde + Glycine RXN0-6563 Glycolaldehyde + NAD + Water > Glycolic acid + NADH 2-amino-4-hydroxy-6-(D-erythro-1,2,3-trihydroxypropyl)-7,8-dihydropteridine > 6-Hydroxymethyl dihydropterin + Glycolaldehyde 7,8-Dihydroneopterin + 7,8-Dihydroneopterin > Glycolaldehyde + 6-Hydroxymethyl dihydropterin PW_R003399 D-Ribulose-1-phosphate <> Glycolaldehyde + Glycerone phosphate PW_R005956 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde 7 7,8-Dihydroneopterin <>6 6-Hydroxymethyl dihydropterin + Glycolaldehyde