2.0 2012-05-31 13:57:41 -0600 2015-09-17 15:41:16 -0600 ECMDB03052 M2MDB000476 Lactaldehyde L-lactaldehyde is an intermediate metabolite in the pyruvate metabolism pathway. L-lactaldehyde is irreversibly produced from pyruvaldehyde via the enzyme aldehyde reductase (EC:1.1.1.21) which is then irreversibly converted to propylene glycol via aldehyde reductase (EC:1.1.1.21). (+-)-2-Hydroxypropanal (2S)-2-hydroxypropanal (S)-lactaldehyde 2-Hydroxypropanal 2-Hydroxypropionaldehyde a-Hydroxypropionaldehyde Alpha-Hydroxypropionaldehyde Hydroxypropionaldehyde L-2-Hydroxypropionaldehyde L-Lactaldehyde Lactald Lactaldehyde α-Hydroxypropionaldehyde C3H6O2 74.079 74.036779433 (2S)-2-hydroxypropanal L-lactaldehyde 598-35-6 [H]C(=O)C(C)O InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3 BSABBBMNWQWLLU-UHFFFAOYSA-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 14.01 ChemAxon pka_strongest_basic -3.2 ChemAxon iupac (2S)-2-hydroxypropanal ChemAxon average_mass 74.079 ChemAxon mono_mass 74.036779433 ChemAxon smiles [H]C(=O)C(C)O ChemAxon formula C3H6O2 ChemAxon inchi InChI=1S/C3H6O2/c1-3(5)2-4/h2-3,5H,1H3 ChemAxon inchikey BSABBBMNWQWLLU-UHFFFAOYSA-N ChemAxon polar_surface_area 37.3 ChemAxon refractivity 17.91 ChemAxon polarizability 7.16 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 fucose and rhamnose degradation In E. coli, L-fucose and L-rhamnose are metabolized through parallel pathways. The pathways converge after their corresponding aldolase reactions yielding the same products: lactaldehye. Via reactions catalyzed by proteins encoded in linked operons comprising a regulon, the methylpentose, alpha-L-rhamnopyranose and/or beta-L-rhamnopyranose, is taken into the cell through a proton symporter and metabolized, enabling E. coli to grow on it as a total source of carbon and energy. For alpha-L-rhamnopyranose, it is isomerized by a l-rhamnose mutarotase resulting in a beta-L-rhamnopyranose which is then isomerized into a keto-L-rhamnulose by a l-rhamnose isomerase. The keto-L-rhamnulose spontaneously changes into a L-rhamnulofuranose which is phosphorylated by a rhamnulokinase resulting in a L-rhamnulose 1-phosphate. This compound reacts with a rhamnulose-1-phosphate aldolase resulting in a dihydroxyacetone phosphate and a lactaldehyde. For beta-L-rhamnopyranose, it is isomerized by a L-fucose mutarotase resulting in a alpha-L-fucopyranose. This compound is then isomerized by an L-fucose isomerase resulting in a L-fuculose which in turn gets phosphorylated into an L-fuculose 1-phosphate through an L-fuculokinase. The compound L-fuculose 1-phosphate reacts with an L-fuculose phosphate aldolase through a dihydroxyacetone phosphate and a lactaldehyde. Two pathways can be used for degradation of L-lactaldehyde. Aerobically, it is converted via lactate to pyruvate, also an intermediate of glycolysis. Anaerobically, lactaldehyde reductase is induced which converts lactaldehyde into propane-1,2-diol. Under aerobic conditions, L-lactaldehyde is oxidized in two steps to pyruvate, thereby channeling all the carbons from fucose or rhamnose into central metabolic pathways. Under anaerobic conditions, L-lactaldehyde is reduced to L-1,2-propanediol, which is secreted into the environment. PW000826 Metabolic L-lactaldehyde degradation (aerobic) L-lactaldehyde is one of two products resulting from degradation of the two methylpentoses L-fucose and rhamnose, which are metabolized by an analogous series of reactions. Aerobically, lactaldehyde is oxidized in two steps to pyruvate, which enters central metabolism. PW002073 Metabolic methylglyoxal degradation IV In this pathway, which has been characterized in Escherichia coli K-12, methylglyoxal is reduced to lactaldehyde by the enzyme methylglyoxal reductase. (S)-lactaldehyde is then reduced to (S)-lactate which is finally converted to pyruvate and joins the pool of central metobolites. Methylglyoxal reductases have been characterized in bacteria and fungi. Some of the enzymes are NADP-linked, while others are NAD-linked. Two variants of this pathway have been entered in MetaCyc to reflect the different biochemistry of the last enzyme, L-lactate dehydrogenase. The Escherichia coli K-12 enzyme encoded by gene lldD uses an unidentified electron acceptor, while the Saccharomyces cerevisiae enzyme uses an an oxidized c-type cytochrome. (EcoCyc) PW002078 Metabolic L-lactaldehyde degradation (aerobic) PWY0-1317 methylglyoxal degradation IV PWY-5459 fucose degradation FUCCAT-PWY L-rhamnose degradation I RHAMCAT-PWY L-lactaldehyde degradation (anaerobic) PWY0-1315 Specdb::CMs 2435 Specdb::CMs 38515 Specdb::CMs 174313 Specdb::MsMs 27830 Specdb::MsMs 27831 Specdb::MsMs 27832 Specdb::MsMs 34388 Specdb::MsMs 34389 Specdb::MsMs 34390 Specdb::MsMs 2669014 Specdb::MsMs 2669015 Specdb::MsMs 2669016 Specdb::MsMs 3013694 Specdb::MsMs 3013695 Specdb::MsMs 3013696 HMDB03052 439231 388368 C05999 18041 LACTALD 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 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 Chen YM, Lin EC: Dual control of a common L-1,2-propanediol oxidoreductase by L-fucose and L-rhamnose in Escherichia coli. J Bacteriol. 1984 Mar;157(3):828-32. 6421801 Casazza JP, Felver ME, Veech RL: The metabolism of acetone in rat. J Biol Chem. 1984 Jan 10;259(1):231-6. 6706932 TING SM, SELLINGER OZ, MILLER ON: THE METABOLISM OF LACTALDEHYDE. VI. THE REDUCTION OF D- AND L-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1964 Aug 26;89:217-25. 14203169 TING SM, MILLER ON, SELLINGER OZ: THE METABOLISM OF LACTALDEHYDE. VII. THE OXIDATION OF D-LACTALDEHYDE IN RAT LIVER. Biochim Biophys Acta. 1965 Mar 8;97:407-15. 14323585 Akhy MT, Brown CM, Old DC: L-Rhamnose utilisation in Salmonella typhimurium. J Appl Bacteriol. 1984 Apr;56(2):269-74. 6373710 Ros J, Aguilar J: Genetic and structural evidence for the presence of propanediol oxidoreductase isoenzymes in Escherichia coli. J Gen Microbiol. 1984 Mar;130(3):687-92. 6427403 Di Costanzo L, Gomez GA, Christianson DW: Crystal structure of lactaldehyde dehydrogenase from Escherichia coli and inferences regarding substrate and cofactor specificity. J Mol Biol. 2007 Feb 16;366(2):481-93. Epub 2006 Nov 10. 17173928 ENGLESBERG E: Physiological basis for rhamnose utilization by a mutant of Pasteurella pestis. I. Experiments with resting cells; the isolation of lactic aldehyde. J Bacteriol. 1957 Jul;74(1):8-11. 13462953 Chen YM, Chakrabarti T, Lin EC: Constitutive activation of L-fucose genes by an unlinked mutation in Escherichia coli. J Bacteriol. 1984 Aug;159(2):725-9. 6378890 SANDMAN RP, MILLER ON: Studies on the metabolism of lactaldehyde. I. Separation and determination of lactaldehyde and related 3-carbon compounds. J Biol Chem. 1958 Jan;230(1):353-9. 13502404 Kranz, Cyrill. Synthesis of Lactic Aldehyde. Chemicke Listy pro Vedu a Prumysl (1912), 5 323-7. 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 Lactaldehyde dehydrogenase P25553 ALDA_ECOLI aldA http://ecmdb.ca/proteins/P25553.xml 2,5-diketo-D-gluconic acid reductase B P30863 DKGB_ECOLI dkgB http://ecmdb.ca/proteins/P30863.xml Rhamnulose-1-phosphate aldolase P32169 RHAD_ECOLI rhaD http://ecmdb.ca/proteins/P32169.xml 2-keto-3-deoxy-L-rhamnonate aldolase P76469 RHMA_ECOLI rhmA http://ecmdb.ca/proteins/P76469.xml 2,5-diketo-D-gluconic acid reductase A Q46857 DKGA_ECOLI dkgA http://ecmdb.ca/proteins/Q46857.xml Putative aldolase class 2 protein ygbL Q46890 YGBL_ECOLI ygbL http://ecmdb.ca/proteins/Q46890.xml L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde R02262 FUCPALDOL-RXN Water + Lactaldehyde + NAD + (S)-Lactaldehyde <>2 Hydrogen ion + L-Lactic acid + NADH R01446 LACTALDDEHYDROG-RXN Hydrogen ion + Lactaldehyde + NADH <> (S)-Propane-1,2-diol + NAD L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde + (S)-Lactaldehyde R02263 RHAMNULPALDOL-RXN Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ion R01446 Propylene glycol + NAD <> Lactaldehyde + NADH + Hydrogen ion R02257 LACTALDREDUCT-RXN 2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde R02261 L-Fuculose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde R02262 L-Rhamnulose 1-phosphate <> Dihydroxyacetone phosphate + Lactaldehyde R02263 Water + NAD + Lactaldehyde > Hydrogen ion + NADH + L-Lactic acid R01446 LACTALDDEHYDROG-RXN Hydrogen ion + NADH + Lactaldehyde <> NAD + Propylene glycol LACTALDREDUCT-RXN Lactaldehyde + NADP < Pyruvaldehyde + NADPH + Hydrogen ion RXN-8636 2-keto-3-deoxy-L-rhamnonate Pyruvic acid + Lactaldehyde RXN0-5433 Lactaldehyde + NAD + Water > L-Lactic acid + NADH L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde (S)-Propane-1,2-diol + NAD > Lactaldehyde + NADH L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + Lactaldehyde L-rhamnulose 1-phosphate + L-Rhamnulose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde PW_R002971 L-fuculose 1-phosphate + L-Fuculose 1-phosphate > Dihydroxyacetone phosphate + (S)-lactaldehyde + Lactaldehyde PW_R002972 NAD + Water + (S)-lactaldehyde + Lactaldehyde > NADH +2 Hydrogen ion + L-Lactic acid + L-Lactic acid PW_R002976 (S)-lactaldehyde + NADH + Hydrogen ion + Lactaldehyde > NAD + Propylene glycol PW_R002977 Pyruvaldehyde + NADPH + Hydrogen ion > Lactaldehyde + NADP PW_R006073 2 2-Dehydro-3-deoxy-L-rhamnonate <> Lactaldehyde + Pyruvic acid + (S)-Lactaldehyde