2.02012-05-31 10:28:05 -06002015-09-13 12:56:08 -0600ECMDB00639M2MDB000162Galactaric acidGalactaric acid is the dicarboxylic sugar acid resulting from oxidation glactose with dilute nitric acid. It is a substrate of galactarate O-hydroxycinnamoyltransferase [EC 2.3.1.130]. (KEGG)(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioate(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid<i>meso</i>-galactarateD-GalactarateD-Galactaric acidGalactarateGalactaric acidGalactosaccharateGalactosaccharic acidHexarateHexaric acidMeso-galactarateMeso-galactaric acidMucateMucic acidSaccharolactateSaccharolactic acidSchleimsaureC6H10O8210.1388210.037567296(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acidmucin526-99-8O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=OInChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-DSLZVSRJTYRBFB-DUHBMQHGSA-NSolidCytosolExtra-organismPeriplasmlogp-1.77logs-0.52solubility6.31e+01 g/lmelting_point220-225 oClogp-3.1pka_strongest_acidic2.83pka_strongest_basic-3.7iupac(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acidaverage_mass210.1388mono_mass210.037567296smilesO[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=OformulaC6H10O8inchiInChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-inchikeyDSLZVSRJTYRBFB-DUHBMQHGSA-Npolar_surface_area155.52refractivity38.14polarizability16.99rotatable_bond_count5acceptor_count8donor_count6physiological_charge-2formal_charge0Ascorbate and aldarate metabolismec00053superpathway of D-glucarate and D-galactarate degradation
Galactarate is a naturally occurring dicarboxylic acid analog of D-galactose. E. coli can use both diacid sugars galactarate and D-glucarate as the sole source of carbon for growth.
The initial step in the degradation of galactarate is its dehydration to 5-dehydro-4-deoxy-D-glucarate(2--) by galactarate dehydratase. Glucaric acid can also be dehydrated by a glucarate dehydratase resulting in water and 5-dehydro-4-deoxy-D-glucarate(2--).
The 5-dehydro-4-deoxy-D-glucarate(2--) is then metabolized by a alpha-dehydro-beta-deoxy-D-glucarate aldolase resulting in pyruvic acid and a tartonate semialdehyde.
Pyruvic acid interacts with coenzyme A through a NAD driven Pyruvate dehydrogenase complex resulting in a carbon dioxide, an NADH and an acetyl-CoA.
The tartronate semialdehyde interacts with a hydrogen ion through a NADPH driven tartronate semialdehyde reductase resulting in a NADP and a glyceric acid. The glyceric acid is phosphorylated by an ATP-driven glycerate kinase 2 resulting in an ADP, a hydrogen ion and a 2-phosphoglyceric acid. The latter compound is dehydrated by an enolase resulting in the release of water and a phosphoenolpyruvic acid.
The phosphoenolpyruvic acid interacts with a hydrogen ion through an ADP driven pyruvate kinase resulting in an ATP and a pyruvic acid. The pyruvic acid then interacts with water and an ATP through a phosphoenolpyruvate synthetase resulting in the release of a hydrogen ion, a phosphate, an AMP and a Phosphoenolpyruvic acid.PW000795MetabolicD-galactarate degradation IGALACTARDEG-PWYSpecdb::CMs1748Specdb::CMs19529Specdb::CMs31180Specdb::CMs37667Specdb::CMs134454Specdb::CMs142188Specdb::CMs146721Specdb::CMs146723Specdb::CMs146725Specdb::CMs279534Specdb::CMs1070881Specdb::CMs1070883Specdb::CMs1070885Specdb::CMs1070887Specdb::CMs1070889Specdb::CMs1070890Specdb::CMs1070892Specdb::CMs1070894Specdb::CMs1070896Specdb::CMs1070898Specdb::CMs1070899Specdb::CMs1070901Specdb::CMs1070903Specdb::CMs1070905Specdb::CMs1070907Specdb::NmrOneD1450Specdb::MsMs873Specdb::MsMs874Specdb::MsMs875Specdb::MsMs4274Specdb::MsMs4275Specdb::MsMs4276Specdb::MsMs4277Specdb::MsMs4278Specdb::MsMs4279Specdb::MsMs309442Specdb::MsMs309443Specdb::MsMs309444Specdb::MsMs353866Specdb::MsMs353867Specdb::MsMs353868Specdb::MsMs438146Specdb::MsMs438147Specdb::MsMs438148Specdb::MsMs438149Specdb::MsMs438150Specdb::MsMs439259Specdb::MsMs2248471Specdb::MsMs2249892Specdb::MsMs2250475Specdb::MsMs2251928Specdb::NmrTwoD1395HMDB0063930375822301286C0087930852D-GALACTARATEGAEMucic 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 80:2939-2948.18331064Fauvarque, Jean-Francois; Guerin, Christophe; Petit, Serge; De Regis, Baynast. Process and electrolytic cell for preparing galactaric acid. Fr. Demande (1994), 14 pp. http://hmdb.ca/system/metabolites/msds/000/000/558/original/HMDB00639.pdf?1358461763D-galactarate dehydrataseP39829GARD_ECOLIgarDhttp://ecmdb.ca/proteins/P39829.xmlProbable glucarate transporterQ46916GUDP_ECOLIgudPhttp://ecmdb.ca/proteins/Q46916.xmlProbable galactarate transporterP0AA80GARP_ECOLIgarPhttp://ecmdb.ca/proteins/P0AA80.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.xmlGalactaric acid > 5-Dehydro-4-deoxy-D-glucarate + WaterGALACTARDEHYDRA-RXND-Galactarate + Galactaric acid <> 5-Dehydro-4-deoxy-D-glucarate + WaterR05608Galactaric acid > Water + 5-dehydro-4-deoxy-D-glucarate(2−)PW_R002723