2.02012-07-30 14:54:38 -06002015-06-03 17:20:38 -0600ECMDB21100M2MDB001509(R)-Propane-1,2-diolPropylene 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)(2R)-propane-1,2-diol(R)-(-)-PROPANE-1,2-DIOL(R)-1,2-propanediol(R)-Propane-1,2-diol(R)-propylene glycol(S)-propane-1,2-diol1,2-Dihydroxypropane1,2-Propane-diol1,2-PropanediolD-1,2-PropanediolPropanediolPropylene glycolR-1,2-PROPANEDIOLC3H8O276.094476.0524295(2R)-propane-1,2-diolR-1,2-propanediol4254-14-2C[C@@H](O)COInChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1DNIAPMSPPWPWGF-GSVOUGTGSA-NCytosolExtra-organismPeriplasmlogp-1.10logs1.10solubility9.52e+02 g/llogp-0.79pka_strongest_acidic14.47pka_strongest_basic-2.9iupac(2R)-propane-1,2-diolaverage_mass76.0944mono_mass76.0524295smilesC[C@@H](O)COformulaC3H8O2inchiInChI=1S/C3H8O2/c1-3(5)2-4/h3-5H,2H2,1H3/t3-/m1/s1inchikeyDNIAPMSPPWPWGF-GSVOUGTGSA-Npolar_surface_area40.46refractivity18.97polarizability8.01rotatable_bond_count1acceptor_count2donor_count2physiological_charge0formal_charge0Pyruvate metabolismec00620Glyoxylate and dicarboxylate metabolismec00630Propanoate 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.PW000940ec00640MetabolicMicrobial metabolism in diverse environmentsec01120Specdb::CMs102837Specdb::CMs102838Specdb::CMs102839Specdb::CMs102840Specdb::CMs102841Specdb::CMs102842Specdb::CMs159349Specdb::EiMs2011Specdb::NmrOneD5264Specdb::NmrOneD5265Specdb::NmrOneD5266Specdb::NmrOneD5267Specdb::NmrOneD5268Specdb::NmrOneD9822Specdb::NmrOneD9823Specdb::NmrOneD9824Specdb::NmrOneD9825Specdb::NmrOneD9826Specdb::NmrOneD9827Specdb::NmrOneD9828Specdb::NmrOneD9829Specdb::NmrOneD9830Specdb::NmrOneD9831Specdb::NmrOneD9832Specdb::NmrOneD9833Specdb::NmrOneD9834Specdb::NmrOneD9835Specdb::NmrOneD9836Specdb::NmrOneD9837Specdb::NmrOneD9838Specdb::NmrOneD9839Specdb::NmrOneD9840Specdb::NmrOneD9841Specdb::MsMs23816Specdb::MsMs23817Specdb::MsMs23818Specdb::MsMs30614Specdb::MsMs30615Specdb::MsMs30616Specdb::MsMs1448608Specdb::MsMs1448609Specdb::MsMs1448610Specdb::MsMs1448611Specdb::MsMs1448612Specdb::MsMs2822372Specdb::MsMs2822373Specdb::MsMs2822374Specdb::MsMs2859781Specdb::MsMs2859782Specdb::MsMs2859783Specdb::NmrTwoD2076259994228188C0291228972CPD-8891PGR(R)-propane-1,2-diolLactaldehyde reductaseP0A9S1FUCO_ECOLIfucOhttp://ecmdb.ca/proteins/P0A9S1.xmlGlycerol dehydrogenaseP0A9S5GLDA_ECOLIgldAhttp://ecmdb.ca/proteins/P0A9S5.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlAcetol + Hydrogen ion + NADH > (R)-Propane-1,2-diol + NAD(R)-Propane-1,2-diol + NAD > D-Lactaldehyde + NADH(R)-Propane-1,2-diol + (S)-Propane-1,2-diol + NAD <> D-Lactaldehyde + (S)-Lactaldehyde + NADH + Hydrogen ionR02258 R03080