2.0 2012-05-31 14:08:30 -0600 2015-06-03 15:54:52 -0600 ECMDB06458 M2MDB000673 D-Lactaldehyde D- and L-lactaldehyde are also good substrates for aldose reductase. The aldose reductase-catalyzed reduction of methylglyoxal produces 95% acetol, 5% D-lactaldehyde. (PMID: 1537826) (2R)-2-hydroxypropanal (R)-Lactaldehyde D-2-Hydroxy-propionaldehyde D-2-Hydroxypropionaldehyde D-Lactaldehyde C3H6O2 74.0785 74.036779436 (2R)-2-hydroxypropanal D-lactaldehyde 3946-09-6 C[C@@H](O)C=O InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1 BSABBBMNWQWLLU-GSVOUGTGSA-N Solid Cytosol logp -1.04 ALOGPS logs 0.95 ALOGPS solubility 6.58e+02 g/l ALOGPS logp -0.63 ChemAxon pka_strongest_acidic 14 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (2R)-2-hydroxypropanal ChemAxon average_mass 74.0785 ChemAxon mono_mass 74.036779436 ChemAxon smiles C[C@@H](O)C=O ChemAxon formula C3H6O2 ChemAxon inchi InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3/t3-/m1/s1 ChemAxon inchikey BSABBBMNWQWLLU-GSVOUGTGSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 17.91 ChemAxon polarizability 7.19 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Fructose and mannose metabolism ec00051 Pyruvate metabolism ec00620 Glyoxylate and dicarboxylate metabolism ec00630 Propanoate metabolism Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA. Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate. Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid. Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA. ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid. Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA. PW000940 ec00640 Metabolic Microbial metabolism in diverse environments ec01120 Specdb::CMs 3115 Specdb::CMs 39017 Specdb::CMs 174947 Specdb::NmrOneD 150200 Specdb::NmrOneD 150201 Specdb::NmrOneD 150202 Specdb::NmrOneD 150203 Specdb::NmrOneD 150204 Specdb::NmrOneD 150205 Specdb::NmrOneD 150206 Specdb::NmrOneD 150207 Specdb::NmrOneD 150208 Specdb::NmrOneD 150209 Specdb::NmrOneD 150210 Specdb::NmrOneD 150211 Specdb::NmrOneD 150212 Specdb::NmrOneD 150213 Specdb::NmrOneD 150214 Specdb::NmrOneD 150215 Specdb::NmrOneD 150216 Specdb::NmrOneD 150217 Specdb::NmrOneD 150218 Specdb::NmrOneD 150219 Specdb::MsMs 25751 Specdb::MsMs 25752 Specdb::MsMs 25753 Specdb::MsMs 32309 Specdb::MsMs 32310 Specdb::MsMs 32311 Specdb::MsMs 2798753 Specdb::MsMs 2798754 Specdb::MsMs 2798755 Specdb::MsMs 2883299 Specdb::MsMs 2883300 Specdb::MsMs 2883301 HMDB06458 439350 388473 C00937 17167 CPD-358 Lactaldehyde 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 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 Vander Jagt, D. L., Robinson, B., Taylor, K. K., Hunsaker, L. A. (1992). "Reduction of trioses by NADPH-dependent aldo-keto reductases. Aldose reductase, methylglyoxal, and diabetic complications." J Biol Chem 267:4364-4369. 1537826 Hazen SL, Hsu FF, d'Avignon A, Heinecke JW: Human neutrophils employ myeloperoxidase to convert alpha-amino acids to a battery of reactive aldehydes: a pathway for aldehyde generation at sites of inflammation. Biochemistry. 1998 May 12;37(19):6864-73. 9578573 HUANG PC, MILLER ON: The metabolism of lactaldehyde. V. Metabolism of L-fucose. J Biol Chem. 1958 Mar;231(1):201-5. 13538961 Lobell, Mario, Grout, David H. G. New insight into the pyruvate decarboxylase-catalyzed formation of lactaldehyde from H-D exchange experiments: a 'water proof' active site. Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic C Lactaldehyde reductase P0A9S1 FUCO_ECOLI fucO http://ecmdb.ca/proteins/P0A9S1.xml Glycerol dehydrogenase P0A9S5 GLDA_ECOLI gldA http://ecmdb.ca/proteins/P0A9S5.xml Glyoxylate/hydroxypyruvate reductase A P75913 GHRA_ECOLI ghrA http://ecmdb.ca/proteins/P75913.xml 2-keto-3-deoxy-L-rhamnonate aldolase P76469 RHMA_ECOLI rhmA http://ecmdb.ca/proteins/P76469.xml Hydrogen ion + Pyruvaldehyde + NADH > D-Lactaldehyde + NAD R02527 D-Lactaldehyde + NAD <> Pyruvaldehyde + NADH + Hydrogen ion R02527 (R)-Propane-1,2-diol + NAD > D-Lactaldehyde + NADH 2-Dehydro-3-deoxy-L-rhamnonate > Pyruvic acid + D-Lactaldehyde (R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion R02258 R03080