2.02012-05-31 10:23:21 -06002015-09-13 12:56:06 -0600ECMDB00190M2MDB000079L-Lactic acidLactic acid plays a role in several biochemical processes. E. coli produces lactic acid from pyruvate in a process of normal metabolism. The lactic acid produced by E. coli and other probiotics (mostly lactic acid bacteria) can lower the pH in mammalian host intestines and therefore, it inhibits the growth of proteolytic bacteria and have a beneficial effect on intestinal inflammation. (PMID 15138208) (+)-Lactate(+)-Lactic acid(a)-Lactate(a)-Lactic acid(alpha)-Lactate(alpha)-Lactic acid(S)-(+)-2-Hydroxypropanoate(S)-(+)-2-Hydroxypropanoic acid(S)-2-hydroxy-Propanoate(S)-2-hydroxy-Propanoic acid(S)-2-Hydroxypropanoate(S)-2-Hydroxypropanoic acid(S)-2-Hydroxypropionate(S)-2-Hydroxypropionic acid(S)-Lactate(S)-Lactic acid(α)-Lactate(α)-Lactic acid1-Hydroxyethane 1-carboxylate1-Hydroxyethane 1-carboxylic acid1-Hydroxyethanecarboxylate1-Hydroxyethanecarboxylic acid2-Hydroxypropanoate2-Hydroxypropanoic acid2-Hydroxypropionate2-Hydroxypropionic acidA-HydroxypropanoateA-Hydroxypropanoic acidA-HydroxypropionateA-Hydroxypropionic acidAlpha-HydroxypropanoateAlpha-Hydroxypropanoic acidAlpha-HydroxypropionateAlpha-Hydroxypropionic acidL(+)-LactateL(+)-Lactic acidL-(+)- LactateL-(+)- Lactic acidL-2-HydroxypropanoateL-2-Hydroxypropanoic acidL-LactateL-Lactic acidLactateLactic acidMilk acidSarcolactateSarcolactic acidα-Hydroxypropanoateα-Hydroxypropanoic acidα-Hydroxypropionateα-Hydroxypropionic acidC3H6O390.077990.031694058(2R)-2-hydroxypropanoic acidD-lactic acid79-33-4C[C@H](O)C(O)=OInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1JVTAAEKCZFNVCJ-REOHCLBHSA-NLiquidCytosolExtra-organismPeriplasmlogp-0.79logs0.79solubility5.62e+02 g/lmelting_point16.8 oC (BP = 119 oC)logp-0.47pka_strongest_acidic3.78pka_strongest_basic-3.7iupac(2R)-2-hydroxypropanoic acidaverage_mass90.0779mono_mass90.031694058smilesC[C@H](O)C(O)=OformulaC3H6O3inchiInChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m0/s1inchikeyJVTAAEKCZFNVCJ-REOHCLBHSA-Npolar_surface_area57.53refractivity18.84polarizability8.05rotatable_bond_count1acceptor_count3donor_count2physiological_charge-1formal_charge0Glycolysis / Gluconeogenesisec00010Pyruvate metabolismec00620Propanoate 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 environmentsec01120Metabolic pathwayseco01100fucose and rhamnose degradationIn 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.
PW000826MetabolicL-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.PW002073Metabolicmethylglyoxal degradation IVIn 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)PW002078MetabolicL-lactaldehyde degradation (aerobic)PWY0-1317Specdb::CMs2962Specdb::CMs38017Specdb::CMs102652Specdb::CMs102653Specdb::CMs102654Specdb::CMs160511Specdb::EiMs1989Specdb::NmrOneD1680Specdb::NmrOneD4830Specdb::NmrOneD4831Specdb::NmrOneD147310Specdb::NmrOneD147311Specdb::NmrOneD147312Specdb::NmrOneD147313Specdb::NmrOneD147314Specdb::NmrOneD147315Specdb::NmrOneD147316Specdb::NmrOneD147317Specdb::NmrOneD147318Specdb::NmrOneD147319Specdb::NmrOneD147320Specdb::NmrOneD147321Specdb::NmrOneD147322Specdb::NmrOneD147323Specdb::NmrOneD147324Specdb::NmrOneD147325Specdb::NmrOneD147326Specdb::NmrOneD147327Specdb::NmrOneD147328Specdb::NmrOneD147329Specdb::MsMs1513Specdb::MsMs1514Specdb::MsMs1515Specdb::MsMs179190Specdb::MsMs179191Specdb::MsMs179192Specdb::MsMs181515Specdb::MsMs181516Specdb::MsMs181517Specdb::MsMs438632Specdb::MsMs2248919Specdb::MsMs2249456Specdb::MsMs2250911Specdb::MsMs3048284Specdb::MsMs3048285Specdb::MsMs3048286Specdb::MsMs3096055Specdb::MsMs3096056Specdb::MsMs3096057Specdb::NmrTwoD1063Specdb::NmrTwoD1621HMDB0019010768996860C0018616651L-LACTATE2OPLactateKeseler, I. 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Faming Zhuanli Shenqing Gongkai Shuomingshu (2007), 9pp. http://hmdb.ca/system/metabolites/msds/000/000/133/original/HMDB00190.pdf?1358462381D-lactate dehydrogenaseP06149DLD_ECOLIdldhttp://ecmdb.ca/proteins/P06149.xmlHydroxyacylglutathione hydrolaseP0AC84GLO2_ECOLIgloBhttp://ecmdb.ca/proteins/P0AC84.xmlLactaldehyde dehydrogenaseP25553ALDA_ECOLIaldAhttp://ecmdb.ca/proteins/P25553.xmlL-lactate dehydrogenase [cytochrome]P33232LLDD_ECOLIlldDhttp://ecmdb.ca/proteins/P33232.xmlUncharacterized protein ykgEP77252YKGE_ECOLIykgEhttp://ecmdb.ca/proteins/P77252.xmlUncharacterized protein ykgGP77433YKGG_ECOLIykgGhttp://ecmdb.ca/proteins/P77433.xmlUncharacterized electron transport protein ykgFP77536YKGF_ECOLIykgFhttp://ecmdb.ca/proteins/P77536.xmlL-lactate permeaseP33231LLDP_ECOLIlldPhttp://ecmdb.ca/proteins/P33231.xmlGlycolate permease glcAQ46839GLCA_ECOLIglcAhttp://ecmdb.ca/proteins/Q46839.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.xmlL-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8L-Lactic acid + Menaquinone 8 > Menaquinol 8 + Pyruvic acidWater + Lactaldehyde + NAD + (S)-Lactaldehyde <>2 Hydrogen ion + L-Lactic acid + NADHR01446LACTALDDEHYDROG-RXNL-Lactic acid + 2 Ferricytochrome c + Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion + Ferrocytochrome cR00196Lactaldehyde + NAD + Water <> L-Lactic acid + NADH + Hydrogen ionR01446an oxidized electron acceptor + L-Lactic acid > a reduced electron acceptor + Pyruvic acidL-LACTDEHYDROGFMN-RXNWater + NAD + Lactaldehyde > Hydrogen ion + NADH + L-Lactic acidR01446LACTALDDEHYDROG-RXNPyruvic acid + Hydrogen ion > L-Lactic acidRXN0-5269Lactaldehyde + NAD + Water > L-Lactic acid + NADHL-Lactic acid + 2 Ferricytochrome c > Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ionNAD + Water + (S)-lactaldehyde + Lactaldehyde > NADH +2 Hydrogen ion + L-Lactic acid + L-Lactic acidPW_R002976L-Lactic acid + oxidized electron acceptor + L-Lactic acid > Reduced acceptor + Pyruvic acidPW_R002978L-Lactic acid + oxidized electron acceptor > Pyruvic acid + reduced electron acceptorPW_R006056L-Lactic acid + Ubiquinone-6 > Pyruvic acid + Ubiquinol-6PW_R006151S-Lactoylglutathione + Water > Glutathione + Hydrogen ion + L-Lactic acidPW_R006150L-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ionL-Lactic acid + 2 Ferricytochrome c <> Pyruvic acid +2 Ferrocytochrome c +2 Hydrogen ion