2.0 2012-07-30 14:54:38 -0600 2015-09-13 12:56:14 -0600 ECMDB21102 M2MDB001511 (S)-Propane-1,2-diol Propylene glycol, also called 1,2-propanediol or propane-1,2-diol, is an organic compound, specifically, a diol or double alcohol. It is a colorless, nearly odorless, clear, viscous liquid, hygroscopic and miscible with water, acetone, and chloroform. Propylene glycol contains an asymmetrical carbon atom, so it exists in two stereoisomers. (Wikipedia) The L or S isomer of propane-1,2-diol can be produced in E. coli by methylglyoxal degradation and anaerobic L-lactaldehyde degradation, where in both processes it is a waste product removed from the cell. (EcoCyc) (2S)-propane-1,2-diol (S)-1,2-propanediol (S)-Propane-1,2-diol (S)-propylene glycol 1,2-Dihydroxypropane 1,2-Propane-diol 1,2-Propanediol L-1,2-Propanediol Propane-1,2-diol Propanediol Propylene glycol S-(+)-Propylene glycol S-1,2-PROPANEDIOL C3H8O2 76.0944 76.0524295 (2S)-propane-1,2-diol (S)-1,2-propanediol 4254-15-3 C[C@H](O)CO InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1 DNIAPMSPPWPWGF-VKHMYHEASA-N Solid logp -1.10 ALOGPS logs 1.10 ALOGPS solubility 9.52e+02 g/l ALOGPS melting_point -59 oC (-74 oF) logp -0.79 ChemAxon pka_strongest_acidic 14.47 ChemAxon pka_strongest_basic -2.9 ChemAxon iupac (2S)-propane-1,2-diol ChemAxon average_mass 76.0944 ChemAxon mono_mass 76.0524295 ChemAxon smiles C[C@H](O)CO ChemAxon formula C3H8O2 ChemAxon inchi InChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m0/s1 ChemAxon inchikey DNIAPMSPPWPWGF-VKHMYHEASA-N ChemAxon polar_surface_area 40.46 ChemAxon refractivity 18.97 ChemAxon polarizability 8.01 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon 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 methylglyoxal degradation III PWY-5453 L-lactaldehyde degradation (anaerobic) PWY0-1315 Specdb::CMs 22547 Specdb::CMs 38965 Specdb::CMs 173552 Specdb::NmrOneD 67832 Specdb::NmrOneD 67833 Specdb::NmrOneD 67834 Specdb::NmrOneD 67835 Specdb::NmrOneD 67836 Specdb::NmrOneD 67837 Specdb::NmrOneD 67838 Specdb::NmrOneD 67839 Specdb::NmrOneD 67840 Specdb::NmrOneD 67841 Specdb::NmrOneD 67842 Specdb::NmrOneD 67843 Specdb::NmrOneD 67844 Specdb::NmrOneD 67845 Specdb::NmrOneD 67846 Specdb::NmrOneD 67847 Specdb::NmrOneD 67848 Specdb::NmrOneD 67849 Specdb::NmrOneD 67850 Specdb::NmrOneD 67851 Specdb::MsMs 24500 Specdb::MsMs 24501 Specdb::MsMs 24502 Specdb::MsMs 31058 Specdb::MsMs 31059 Specdb::MsMs 31060 Specdb::MsMs 2740525 Specdb::MsMs 2740526 Specdb::MsMs 2740527 Specdb::MsMs 2937751 Specdb::MsMs 2937752 Specdb::MsMs 2937753 HMDB06213 439846 388890 C02917 29002 PROPANE-1-2-DIOL PGQ (S)-propane-1,2-diol 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 http://hmdb.ca/system/metabolites/msds/000/005/338/original/HMDB06213.pdf?1358463397 Lactaldehyde reductase P0A9S1 FUCO_ECOLI fucO http://ecmdb.ca/proteins/P0A9S1.xml Outer membrane protein N P77747 OMPN_ECOLI ompN http://ecmdb.ca/proteins/P77747.xml Outer membrane pore protein E P02932 PHOE_ECOLI phoE http://ecmdb.ca/proteins/P02932.xml Outer membrane protein F P02931 OMPF_ECOLI ompF http://ecmdb.ca/proteins/P02931.xml Outer membrane protein C P06996 OMPC_ECOLI ompC http://ecmdb.ca/proteins/P06996.xml Hydrogen ion + Lactaldehyde + NADH <> (S)-Propane-1,2-diol + NAD (S)-Propane-1,2-diol + NAD > Lactaldehyde + NADH (R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ion R02258 R03080