2.0 2012-05-31 10:28:05 -0600 2015-09-13 12:56:08 -0600 ECMDB00639 M2MDB000162 Galactaric acid Galactaric 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>-galactarate D-Galactarate D-Galactaric acid Galactarate Galactaric acid Galactosaccharate Galactosaccharic acid Hexarate Hexaric acid Meso-galactarate Meso-galactaric acid Mucate Mucic acid Saccharolactate Saccharolactic acid Schleimsaure C6H10O8 210.1388 210.037567296 (2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid mucin 526-99-8 O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O InChI=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-N Solid Cytosol Extra-organism Periplasm logp -1.77 ALOGPS logs -0.52 ALOGPS solubility 6.31e+01 g/l ALOGPS melting_point 220-225 oC logp -3.1 ChemAxon pka_strongest_acidic 2.83 ChemAxon pka_strongest_basic -3.7 ChemAxon iupac (2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid ChemAxon average_mass 210.1388 ChemAxon mono_mass 210.037567296 ChemAxon smiles O[C@@H]([C@@H](O)[C@H](O)C(O)=O)[C@@H](O)C(O)=O ChemAxon formula C6H10O8 ChemAxon inchi InChI=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- ChemAxon inchikey DSLZVSRJTYRBFB-DUHBMQHGSA-N ChemAxon polar_surface_area 155.52 ChemAxon refractivity 38.14 ChemAxon polarizability 16.99 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 8 ChemAxon donor_count 6 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 superpathway 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. PW000795 Metabolic D-galactarate degradation I GALACTARDEG-PWY Specdb::CMs 1748 Specdb::CMs 19529 Specdb::CMs 31180 Specdb::CMs 37667 Specdb::CMs 134454 Specdb::CMs 142188 Specdb::CMs 146721 Specdb::CMs 146723 Specdb::CMs 146725 Specdb::CMs 279534 Specdb::CMs 1070881 Specdb::CMs 1070883 Specdb::CMs 1070885 Specdb::CMs 1070887 Specdb::CMs 1070889 Specdb::CMs 1070890 Specdb::CMs 1070892 Specdb::CMs 1070894 Specdb::CMs 1070896 Specdb::CMs 1070898 Specdb::CMs 1070899 Specdb::CMs 1070901 Specdb::CMs 1070903 Specdb::CMs 1070905 Specdb::CMs 1070907 Specdb::NmrOneD 1450 Specdb::MsMs 873 Specdb::MsMs 874 Specdb::MsMs 875 Specdb::MsMs 4274 Specdb::MsMs 4275 Specdb::MsMs 4276 Specdb::MsMs 4277 Specdb::MsMs 4278 Specdb::MsMs 4279 Specdb::MsMs 309442 Specdb::MsMs 309443 Specdb::MsMs 309444 Specdb::MsMs 353866 Specdb::MsMs 353867 Specdb::MsMs 353868 Specdb::MsMs 438146 Specdb::MsMs 438147 Specdb::MsMs 438148 Specdb::MsMs 438149 Specdb::MsMs 438150 Specdb::MsMs 439259 Specdb::MsMs 2248471 Specdb::MsMs 2249892 Specdb::MsMs 2250475 Specdb::MsMs 2251928 Specdb::NmrTwoD 1395 HMDB00639 3037582 2301286 C00879 30852 D-GALACTARATE GAE Mucic acid 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 van 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. 17765195 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." Anal Chem 80:2939-2948. 18331064 Fauvarque, 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?1358461763 D-galactarate dehydratase P39829 GARD_ECOLI garD http://ecmdb.ca/proteins/P39829.xml Probable glucarate transporter Q46916 GUDP_ECOLI gudP http://ecmdb.ca/proteins/Q46916.xml Probable galactarate transporter P0AA80 GARP_ECOLI garP http://ecmdb.ca/proteins/P0AA80.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 Galactaric acid > 5-Dehydro-4-deoxy-D-glucarate + Water GALACTARDEHYDRA-RXN D-Galactarate + Galactaric acid <> 5-Dehydro-4-deoxy-D-glucarate + Water R05608 Galactaric acid > Water + 5-dehydro-4-deoxy-D-glucarate(2−) PW_R002723