2.0 2012-05-31 13:49:42 -0600 2015-09-13 12:56:10 -0600 ECMDB01311 M2MDB000334 D-Lactic acid D-Lactic acid is the end product of the enzyme Glyoxalase ([EC:3.1.2.6] hydroxyacyl-glutathione hydrolase) which converts the intermediate substrate S-lactoyl-glutathione to reduced glutathione and D-lactate. (OMIM 138790) (-)-Lactate (-)-Lactic acid (R)-2-hydroxypropanate (R)-(-)-Lactate (R)-(-)-Lactic acid (R)-2-hydroxypropanate (R)-2-hydroxypropanic acid (R)-2-Hydroxypropanoate (R)-2-Hydroxypropanoic acid (R)-2-Hydroxypropionate (R)-2-Hydroxypropionic acid (R)-a-Hydroxypropionate (R)-a-Hydroxypropionic acid (R)-alpha-Hydroxypropionate (R)-alpha-Hydroxypropionic acid (R)-Lactate (R)-Lactic acid (R)-α-Hydroxypropionate (R)-α-Hydroxypropionic acid D-(-)-Lactate D-(-)-Lactic acid D-2-Hydroxypropanoate D-2-Hydroxypropanoic acid D-2-Hydroxypropionate D-2-Hydroxypropionic acid D-Lactate D-Lactic acid Delta-(-)-Lactate Delta-(-)-Lactic acid Delta-2-Hydroxypropanoate Delta-2-Hydroxypropanoic acid Delta-2-Hydroxypropionate Delta-2-Hydroxypropionic acid Delta-Lactate Delta-Lactic acid DLA L-(+)-Lactate L-(+)-Lactic acid L-Lactate L-Lactic acid Propel Tisulac δ-(-)-Lactate δ-(-)-Lactic acid δ-2-Hydroxypropanoate δ-2-Hydroxypropanoic acid δ-2-Hydroxypropionate δ-2-Hydroxypropionic acid δ-Lactate δ-Lactic acid C3H6O3 90.0779 90.031694058 (2S)-2-hydroxypropanoic acid (α)-lactate 10326-41-7 C[C@@H](O)C(O)=O InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1 JVTAAEKCZFNVCJ-UWTATZPHSA-N Solid Cytosol Extra-organism Periplasm melting_point 52.8 C logp -0.47 ChemAxon pka_strongest_acidic 3.78 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2S)-2-hydroxypropanoic acid ChemAxon average_mass 90.0779 ChemAxon mono_mass 90.031694058 ChemAxon smiles C[C@@H](O)C(O)=O ChemAxon formula C3H6O3 ChemAxon inchi InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)/t2-/m1/s1 ChemAxon inchikey JVTAAEKCZFNVCJ-UWTATZPHSA-N ChemAxon polar_surface_area 57.53 ChemAxon refractivity 18.84 ChemAxon polarizability 8.06 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Amino sugar and nucleotide sugar metabolism ec00520 Pyruvate metabolism ec00620 Microbial metabolism in diverse environments ec01120 Amino sugar and nucleotide sugar metabolism I The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound can either be isomerized or deaminated into Beta-D-fructofuranose 6-phosphate through a glucosamine-fructose-6-phosphate aminotransferase and a glucosamine-6-phosphate deaminase respectively. Glucosamine 6-phosphate undergoes a reversible reaction to glucosamine 1 phosphate through a phosphoglucosamine mutase. This compound is then acetylated through a bifunctional protein glmU to produce a N-Acetyl glucosamine 1-phosphate. N-Acetyl glucosamine 1-phosphate enters the nucleotide sugar synthesis by reacting with UTP and hydrogen ion through a bifunctional protein glmU releasing pyrophosphate and a Uridine diphosphate-N-acetylglucosamine.This compound can either be isomerized into a UDP-N-acetyl-D-mannosamine or undergo a reaction with phosphoenolpyruvic acid through UDP-N-acetylglucosamine 1-carboxyvinyltransferase releasing a phosphate and a UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate. UDP-N-acetyl-D-mannosamine undergoes a NAD dependent dehydrogenation through a UDP-N-acetyl-D-mannosamine dehydrogenase, releasing NADH, a hydrogen ion and a UDP-N-Acetyl-alpha-D-mannosaminuronate, This compound is then used in the production of enterobacterial common antigens. UDP-N-Acetyl-alpha-D-glucosamine-enolpyruvate is reduced through a NADPH dependent UDP-N-acetylenolpyruvoylglucosamine reductase, releasing a NADP and a UDP-N-acetyl-alpha-D-muramate. This compound is involved in the D-glutamine and D-glutamate metabolism. PW000886 Metabolic Amino sugar and nucleotide sugar metabolism II The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. The beta-D-fructofuranose 6 -phosphate is isomerized in a reversible reaction into an alpha-D-mannose 6-phosphate. This compound can also be introduced into the cell from the periplasmic space through a mannose PTS permease that phosphorylates an alpha-D-mannose. Alpha-D-mannose 6-phosphate undergoes a reversible reaction through a phosphomannomutase to produce an alpha-D-mannose 1-phosphate. The alpha-D-mannose 1-phosphate enters the nucleotide sugar metabolism through a reaction with GTP producing a GDP-mannose and releasing a pyrophosphate, all through a mannose-1-phosphate guanylyltransferase. GDP-mannose is then dehydrated to produce GDP-4-dehydro-6-deoxy-alpha-D-mannose through a GDP-mannose 4,6-dehydratase. This compound is then used to synthesize GDP-Beta-L-fucose through a NADPH dependent GDP-L-fucose synthase. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000887 Metabolic Amino sugar and nucleotide sugar metabolism III The synthesis of amino sugars and nucleotide sugars starts with the phosphorylation of N-Acetylmuramic acid (MurNac) through its transport from the periplasmic space to the cytoplasm. Once in the cytoplasm, MurNac and water undergo a reversible reaction through a N-acetylmuramic acid 6-phosphate etherase, producing a D-lactic acid and N-Acetyl-D-Glucosamine 6-phosphate. This latter compound can also be introduced into the cytoplasm through a phosphorylating PTS permase in the inner membrane that allows for the transport of N-Acetyl-D-glucosamine from the periplasmic space. N-Acetyl-D-Glucosamine 6-phosphate can also be obtained from chitin dependent reactions. Chitin is hydrated through a bifunctional chitinase to produce chitobiose. This in turn gets hydrated by a beta-hexosaminidase to produce N-acetyl-D-glucosamine. The latter undergoes an atp dependent phosphorylation leading to the production of N-Acetyl-D-Glucosamine 6-phosphate. N-Acetyl-D-Glucosamine 6-phosphate is then be deacetylated in order to produce Glucosamine 6-phosphate through a N-acetylglucosamine-6-phosphate deacetylase. This compound is then deaminased into Beta-D-fructofuranose 6-phosphate through a glucosamine-6-phosphate deaminase. Beta-D-fructofuranose 6-phosphate is isomerized into a beta-D-glucose 6-phosphate through a glucose-6-phosphate isomerase. The compound is then isomerized by a putative beta-phosphoglucomutase to produce a beta-D-glucose 1-phosphate. This compound enters the nucleotide sugar metabolism through uridylation resulting in a UDP-glucose. UDP-glucose is then dehydrated through a UDP-glucose 6-dehydrogenase to produce a UDP-glucuronic acid. This compound undergoes a NAD dependent reaction through a bifunctional polymyxin resistance protein to produce UDP-Beta-L-threo-pentapyranos-4-ulose. This compound then reacts with L-glutamic acid through a UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase to produce an oxoglutaric acid and UDP-4-amino-4-deoxy-beta-L-arabinopyranose The latter compound interacts with a N10-formyl-tetrahydrofolate through a bifunctional polymyxin resistance protein ArnA, resulting in a tetrahydrofolate, a hydrogen ion and a UDP-4-deoxy-4-formamido-beta-L-arabinopyranose, which in turn reacts with a product of the methylerythritol phosphate and polysoprenoid biosynthesis pathway, di-trans,octa-cis-undecaprenyl phosphate to produce a 4-deoxy-4-formamido-alpha-L-arabinopyranosyl ditrans, octacis-undecaprenyl phosphate. Alpha-D-glucose is introduced into the cytoplasm through a glucose PTS permease, which phosphorylates the compound in order to produce an alpha-D-glucose 6-phosphate. This compound is then modified through a phosphoglucomutase 1 to yield alpha-D-glucose 1-phosphate. This compound can either be adenylated to produce ADP-glucose or uridylylated to produce galactose 1-phosphate through glucose-1-phosphate adenyllyltransferase and galactose-1-phosphate uridylyltransferase respectively. PW000895 Metabolic 1,6-anhydro-N-acetylmuramic acid recycling Anhydromuropeptides (mainly GlcNAc-1,6-anhMurNAc-L-Ala-γ-D-Glu-DAP-D-Ala) are steadily released during growth by lytic transglycosylases and endopeptidases and imported back into the cytoplasm for recycling. During bacterial growth, a very large proportion of the peptidoglycan polymer is degraded and reused in a process termed cell wall recycling. For example, the Gram-negative bacterium Escherichia coli recovers about half of its cell wall within one generation. The anhydromuropeptides are imported by the ampG-encoded muropeptide:H+ symporter. Once inside the cytoplasm, the anhydromuropeptides are hydrolyzed by N-acetylmuramoyl-L-alanine amidase (ampD), β-N-acetylhexosaminidase (nagZ) and L,D-carboxypeptidase A (ldcA), yielding N-acetyl-β-D-glucosamine, 1,6-anhydro-N-acetyl-β-muramate, L-alanyl-γ-D-glutamyl-meso-diaminopimelate and D-alanine. 1,6-anhydro-N-acetyl-β-muramate is phosphorylated by anhydro-N-acetylmuramic acid kinase (anmK) and then converted into N-acetyl-D-glucosamine 6-phosphate by N-acetylmuramic acid 6-phosphate etherase (murQ). This is a branch point, as this compound could be directed either for further degradation or for recycling into new peptidoglycan monomers, as described in this pathway. The final product of this pathway, UDP-N-acetyl-α-D-muramate, is one of the precursors for peptidoglycan biosynthesis. The tripeptide L-alanyl-γ-D-glutamyl-meso-diaminopimelate, which is generated by muramoyltetrapeptide carboxypeptidase, can be degraded further, as described in muropeptide degradation. However, the vast majority is recycled by muropeptide ligase (mpl). This enzyme is a dedicated recycling enzyme that attaches the recovered Ala-Glu-DAP tripeptide to UDP-N-acetyl-α-D-muramate, thereby substituting three amino acid ligases of the peptidoglycan de novobiosynthetic pathway. Although exogenously provided 1,6-anhydro-N-acetyl-β-muramate can be taken up by Escherichia coli, it can not serve as the sole source of carbon for growth, suggesting that it may be toxic to the cell. (EcoCyc) PW002064 Metabolic methylglyoxal degradation II The most common pathway for methylglyoxal detoxification is the glyoxalase system, which is composed of two enzymes that together convert methylglyoxal to (R)-lactate in the presence of glutathione. However, in E. coli, a single enzyme, glyoxalase III, catalyzes this conversion in a single step without involvement of glutathione. Activity of glyoxalase III increases at the transition to stationary phase and expression is dependent on RpoS, suggesting that this pathway may be important during stationary phase. (EcoCyc) PW002084 Metabolic mixed acid fermentation FERMENTATION-PWY methylglyoxal degradation I PWY-5386 methylglyoxal degradation II PWY-901 1,6-anhydro-N-acetylmuramic acid recycling PWY0-1261 Specdb::CMs 434 Specdb::CMs 2365 Specdb::CMs 30161 Specdb::CMs 30601 Specdb::CMs 37346 Specdb::CMs 152925 Specdb::CMs 1053840 Specdb::CMs 1053841 Specdb::CMs 1053843 Specdb::CMs 1053845 Specdb::CMs 1053847 Specdb::EiMs 1087 Specdb::NmrOneD 1162 Specdb::NmrOneD 1197 Specdb::NmrOneD 4808 Specdb::NmrOneD 6072 Specdb::NmrOneD 6073 Specdb::NmrOneD 6074 Specdb::NmrOneD 6075 Specdb::NmrOneD 6076 Specdb::NmrOneD 6077 Specdb::NmrOneD 6078 Specdb::NmrOneD 6079 Specdb::NmrOneD 6080 Specdb::NmrOneD 6081 Specdb::NmrOneD 6082 Specdb::NmrOneD 6083 Specdb::NmrOneD 6084 Specdb::NmrOneD 6085 Specdb::NmrOneD 6086 Specdb::NmrOneD 6087 Specdb::NmrOneD 6088 Specdb::NmrOneD 6089 Specdb::NmrOneD 6090 Specdb::NmrOneD 6091 Specdb::NmrOneD 166457 Specdb::MsMs 301 Specdb::MsMs 302 Specdb::MsMs 303 Specdb::MsMs 3467 Specdb::MsMs 3468 Specdb::MsMs 3469 Specdb::MsMs 3470 Specdb::MsMs 3471 Specdb::MsMs 178011 Specdb::MsMs 178012 Specdb::MsMs 178013 Specdb::MsMs 180324 Specdb::MsMs 180325 Specdb::MsMs 180326 Specdb::MsMs 438026 Specdb::MsMs 438027 Specdb::MsMs 438028 Specdb::MsMs 438029 Specdb::MsMs 438030 Specdb::MsMs 1474450 Specdb::MsMs 2258028 Specdb::MsMs 2258582 Specdb::MsMs 2260001 Specdb::MsMs 3055172 Specdb::MsMs 3055173 Specdb::NmrTwoD 989 Specdb::NmrTwoD 1195 HMDB01311 61503 55423 C00256 341 D-LACTATE LAC DLA 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." 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U.S. (1997), 5 pp. http://hmdb.ca/system/metabolites/msds/000/001/173/original/HMDB01311.pdf?1358461953 D-lactate dehydrogenase P06149 DLD_ECOLI dld http://ecmdb.ca/proteins/P06149.xml Hydroxyacylglutathione hydrolase P0AC84 GLO2_ECOLI gloB http://ecmdb.ca/proteins/P0AC84.xml D-lactate dehydrogenase_ P52643 LDHD_ECOLI ldhA http://ecmdb.ca/proteins/P52643.xml N-acetylmuramic acid 6-phosphate etherase P76535 MURQ_ECOLI murQ http://ecmdb.ca/proteins/P76535.xml Molecular chaperone Hsp31 and glyoxalase 3 P31658 hchA http://ecmdb.ca/proteins/P31658.xml L-lactate permease P33231 LLDP_ECOLI lldP http://ecmdb.ca/proteins/P33231.xml Glycolate permease glcA Q46839 GLCA_ECOLI glcA http://ecmdb.ca/proteins/Q46839.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 D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid R00704 DLACTDEHYDROGNAD-RXN Water + S-Lactoylglutathione > Glutathione + Hydrogen ion + D-Lactic acid R01736 GLYOXII-RXN D-Lactic acid + Ubiquinone-8 > Pyruvic acid + Ubiquinol-8 N-Acetylmuramic acid 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid R08555 RXN0-4641 S-Lactoylglutathione + Water <> Glutathione + D-Lactic acid R01736 GLYOXII-RXN an electron-transfer-related quinone + D-Lactic acid > an electron-transfer-related quinol + Pyruvic acid DLACTDEHYDROGFAD-RXN NAD + D-Lactic acid < Hydrogen ion + NADH + Pyruvic acid DLACTDEHYDROGNAD-RXN D-Lactic acid + Hydrogen ion < Pyruvaldehyde + Water GLYOXIII-RXN D-Lactic acid + NAD > Pyruvic acid + NADH D-Lactic acid > Pyruvaldehyde + Water GLYOXIII-RXN N-Acetylmuramic acid 6-phosphate + Water > N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid D-Lactic acid <> Pyruvaldehyde + Water R09796 MurNAc-6-P + Water > D-Lactic acid + N-Acetylglucosamine 6-phosphate PW_R003303 Pyruvaldehyde + Water > D-Lactic acid + Hydrogen ion PW_R006086 N-Acetylmuramate 6-phosphate + Water <> N-Acetyl-D-Glucosamine 6-Phosphate + D-Lactic acid PW_R006028 D-Lactic acid + 2 Hydrogen ion + an ubiquinol > Pyruvic acid + ubiquinone PW_R006087 D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid D-Lactic acid <> Pyruvaldehyde + Water D-Lactic acid + NAD <> Hydrogen ion + NADH + Pyruvic acid D-Lactic acid <> Pyruvaldehyde + Water