2.02012-05-31 13:02:24 -06002015-09-13 12:56:09 -0600ECMDB00956M2MDB000206Tartaric acidTartaric acid is a white crystalline organic acid. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. (Wikipedia) In E. coli K-12, tartaric acid is involved in glyoxylate and dicarboxylate metabolism. (KEGG)(+)-(2R,3R)-Tartarate(+)-(2R,3R)-Tartaric acid(+)-tartarate(+)-tartaric acid(+)-tartrate(+)-tartric acid(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylate(1R,2R)-1,2-Dihydroxyethane-1,2-dicarboxylic acid(2R,3R)-2,3-dihydroxybutanedioate(2R,3R)-2,3-dihydroxybutanedioic acid(2R,3R)-2,3-dihydroxysuccinate(2R,3R)-2,3-dihydroxysuccinic acid(2R,3R)-2,3-tartarate(2R,3R)-2,3-tartaric acid(2R,3R)-Tartarate(2R,3R)-Tartaric acid(2R,3R)-tartrate(2R,3R)-tartric acid(R,R)-(+)-tartarate(R,R)-(+)-tartaric acid(R,R)-tartarate(R,R)-tartaric acid(R,R)-tartrate(R,R)-tartric acid1,2-Dihydroxyethane-1,2-dicarboxylate1,2-Dihydroxyethane-1,2-dicarboxylic acid2,3-Dihydroxy-succinate2,3-Dihydroxy-succinic acid2,3-Dihydroxybutanedioate2,3-Dihydroxybutanedioic acid2,3-Dihydroxysuccinate2,3-Dihydroxysuccinic acidD-a,b-DihydroxysuccinateD-a,b-Dihydroxysuccinic acidD-TartarateD-Tartaric acidDextrotartarateDextrotartaric acidL(+)-TartarateL(+)-Tartaric acidL-(+)-TartarateL-(+)-Tartaric acidL-TartarateL-Tartaric acidL-ThrearateL-Threaric acidNatural tartarateNatural tartaric acidRechtsweinsaeureTARTartarateTartaric acidTartrateTartric acidThrearateThrearic acidTLAWeinsaeureC4H6O6150.0868150.016437924(2R,3R)-2,3-dihydroxybutanedioic acidL(+)-tartaric acid87-69-4O[C@H]([C@@H](O)C(O)=O)C(O)=OInChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1FEWJPZIEWOKRBE-JCYAYHJZSA-NSolidCytosolExtra-organismPeriplasmlogp-1.27logs0.03solubility1.61e+02 g/lmelting_point169 oClogp-1.8pka_strongest_acidic2.72pka_strongest_basic-4.3iupac(2R,3R)-2,3-dihydroxybutanedioic acidaverage_mass150.0868mono_mass150.016437924smilesO[C@H]([C@@H](O)C(O)=O)C(O)=OformulaC4H6O6inchiInChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m1/s1inchikeyFEWJPZIEWOKRBE-JCYAYHJZSA-Npolar_surface_area115.06refractivity26.21polarizability11.33rotatable_bond_count3acceptor_count6donor_count4physiological_charge-2formal_charge0Butanoate metabolismec00650Glyoxylate and dicarboxylate metabolismec00630inner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786Metabolicglycolate and glyoxylate degradation IIOxaloglycolate (2-Hydroxy-3-oxosuccinate) interacts with a tartrate dehydrogenase resulting in a L-tartrate. L-tartrate then interacts with tartrate dehydrogenase resulting in a Oxaloacetate. Oxaloacetate and acetyl-coa interact to result in a citrate which is processed by a aconitate hydratase resulting in a cis-Aconitate and further more into a isocitrate which will eventually be procressed into a glyoxylic acid. Glyoxylic acid can either be metabolized into L-malic acid by a reaction with acetyl-CoA and Water through a malate synthase G which also releases hydrogen ion and Coenzyme A. L-malic acid is then incorporated into the TCA cycle. Glyoxylic acid can also be metabolized by glyoxylate carboligase, releasing a carbon dioxide and tartronate semialdehyde. The latter compound is then reduced by an NADH driven tartronate semialdehyde reductase 2 resulting in glyceric acid. Glyceric acid is phosphorylated by a glycerate kinase 2 resulting in a 3-phosphoglyceric acid. This compound is then integrated into various other pathways: cysteine biosynthesis, serine biosynthesis and glycolysis and pyruvate dehydrogenase.PW002021MetabolicSpecdb::CMs684Specdb::CMs1308Specdb::CMs6360Specdb::CMs30027Specdb::CMs30587Specdb::CMs31268Specdb::CMs149840Specdb::CMs1082476Specdb::CMs1082477Specdb::CMs1082478Specdb::CMs1082479Specdb::CMs1082480Specdb::CMs1082481Specdb::CMs1082482Specdb::CMs1082483Specdb::CMs1082484Specdb::CMs1082485Specdb::CMs1082486Specdb::CMs1082487Specdb::CMs1082488Specdb::CMs1082489Specdb::CMs1082490Specdb::CMs1082491Specdb::CMs1082492Specdb::CMs1082493Specdb::EiMs2005Specdb::NmrOneD1621Specdb::NmrOneD8042Specdb::NmrOneD8043Specdb::NmrOneD8044Specdb::NmrOneD8045Specdb::NmrOneD8046Specdb::NmrOneD8047Specdb::NmrOneD8048Specdb::NmrOneD8049Specdb::NmrOneD8050Specdb::NmrOneD8051Specdb::NmrOneD8052Specdb::NmrOneD8053Specdb::NmrOneD8054Specdb::NmrOneD8055Specdb::NmrOneD8056Specdb::NmrOneD8057Specdb::NmrOneD8058Specdb::NmrOneD8059Specdb::NmrOneD8060Specdb::NmrOneD8061Specdb::MsMs1354Specdb::MsMs1355Specdb::MsMs1356Specdb::MsMs4963Specdb::MsMs4964Specdb::MsMs4965Specdb::MsMs4966Specdb::MsMs4967Specdb::MsMs247110Specdb::MsMs247111Specdb::MsMs247112Specdb::MsMs267054Specdb::MsMs267055Specdb::MsMs267056Specdb::MsMs438513Specdb::MsMs438514Specdb::MsMs438515Specdb::MsMs438516Specdb::MsMs438517Specdb::MsMs2256903Specdb::MsMs2257705Specdb::MsMs2258850Specdb::MsMs2259705Specdb::MsMs2736833Specdb::MsMs2736834Specdb::NmrTwoD1050Specdb::NmrTwoD1562HMDB00956444305392277C0089815671TARTRATETLATartaric acidKeseler, 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-D590.21097882Kanehisa, 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-D114.22080510van 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 370:17-25.17765195Winder, 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." Anal Chem 80:2939-2948.18331064Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4.19212411Petrarulo M, Marangella M, Bianco O, Linari F: Ion-chromatographic determination of L-tartrate in urine samples. Clin Chem. 1991 Jan;37(1):90-3.1988215Lord RS, Burdette CK, Bralley JA: Significance of urinary tartaric acid. Clin Chem. 2005 Mar;51(3):672-3.15738524Milas, N. A.; Terry, Ethel M. Oxidation of fumaric and of maleic acids to tartaric acid. Journal of the American Chemical Society (1925), 47 1412-8.http://hmdb.ca/system/metabolites/msds/000/000/860/original/HMDB00956.pdf?1358461643L(+)-tartrate dehydratase subunit alphaP05847TTDA_ECOLIttdAhttp://ecmdb.ca/proteins/P05847.xmlL(+)-tartrate dehydratase subunit betaP0AC35TTDB_ECOLIttdBhttp://ecmdb.ca/proteins/P0AC35.xmlD-malate dehydrogenase [decarboxylating]P76251DMLA_ECOLIdmlAhttp://ecmdb.ca/proteins/P76251.xmlL-tartrate/succinate antiporterP39414TTDT_ECOLIttdThttp://ecmdb.ca/proteins/P39414.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.xmlTartaric acid <> Water + Oxalacetic acidR00339LTARTDEHYDRA-RXNTartaric acid <> Glyceric acid + Carbon dioxideR01751Tartaric acid + NAD <> 2-Hydroxy-3-oxosuccinate + NADH + Hydrogen ionR06180Tartaric acid > Oxalacetic acid + Water