2.0 2012-05-31 14:36:25 -0600 2015-09-17 15:41:58 -0600 ECMDB20271 M2MDB001113 3-Keto-L-gulonate 6-phosphate 3-keto-L-gulonate 6-phosphate is a member of the chemical class known as Medium-chain Keto Acids and Derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 3-Dehydro-L-gulonate-6-phosphate 3-dehydro-L-Gulonic acid-6-phosphoric acid 3-Keto-L-gulonate 6-P 3-Keto-L-gulonate-6-phosphate 3-Keto-L-gulonic acid 6-P 3-Keto-L-gulonic acid 6-phosphate 3-keto-L-Gulonic acid 6-phosphoric acid 3-keto-L-Gulonic acid-6-phosphoric acid C6H9O10P 272.103 271.994430648 2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid 2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid OC(COP([O-])([O-])=O)C(O)C(=O)C(O)C(O)=O InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/p-2 BDUIIKXSXFDPEC-UHFFFAOYSA-L Cytoplasm Periplasm logp -2.13 ALOGPS logs -1.22 ALOGPS solubility 1.64e+01 g/l ALOGPS logp -2.8 ChemAxon pka_strongest_acidic 1.47 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac 2,4,5-trihydroxy-3-oxo-6-(phosphonooxy)hexanoic acid ChemAxon average_mass 272.103 ChemAxon mono_mass 271.994430648 ChemAxon smiles OC(COP([O-])([O-])=O)C(O)C(=O)C(O)C(O)=O ChemAxon formula C6H9O10P ChemAxon inchi InChI=1S/C6H11O10P/c7-2(1-16-17(13,14)15)3(8)4(9)5(10)6(11)12/h2-3,5,7-8,10H,1H2,(H,11,12)(H2,13,14,15)/p-2 ChemAxon inchikey BDUIIKXSXFDPEC-UHFFFAOYSA-L ChemAxon polar_surface_area 181.82 ChemAxon refractivity 48.45 ChemAxon polarizability 20.86 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 9 ChemAxon donor_count 6 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Ascorbate metabolism E. coli is able to utilize L-ascorbate (vitamin C) as the sole source of carbon under anaerobic and aerobic conditions. Ascorbic acid in the cytoplasm is processed through a spontaneous reaction with a hydrogen ion and hydrogen peroxide, producing water, dehydroascorbic acid and ascorbic acid. Dehydroascorbic acid reacts with water spontaneously producing an isomer, dehydroascorbate (bicyclic form). The compound then loses a hydrogen ion resulting in a 2,3-Diketo-L-gulonate. This compound is then reduced through a NADH dependent 2,3 diketo-L-gulonate reductase, releasing a NAD and 3-Dehydro-L-gulonate.This compound is phosphorylated through an ATP mediated L-xylulose/3-keto-L-gulonate kinase resulting in an ADP, hydrogen ion and a 3-Keto-L-gulonate 6 phosphate. L-ascorbate can also be imported and converted to L-ascorbate-6-phosphate by the L-ascorbate PTS transporter. L-ascorbate-6-phosphate reacts with a probable L-ascorbate-6-phosphate lactonase ulaG, resulting in a 3-keto-L-gulonate 6-phosphate. The compound 3-keto-L-gulonate 6-phosphate can be processed aerobically or anaerobically. Aerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by a 3-keto-L-gulonate-6-phosphate decarboxylase ulaD, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by L-ribulose-5-phosphate 3-epimerase ulaE, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase ulaF resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Anaerobic: 3-keto-L-gulonate 6-phosphate is decarboxylated by 3-keto-L-gulonate 6-phosphate decarboxylase sgbH, releasing carbon dioxide and L-xylulose-5-phosphate. This compound in turn is changed into an isomer by predicted L-xylulose 5-phosphate 3-epimerase, resulting in L-ribulose 5-phosphate. This compound again changes into a different isomer through a L-ribulose-5-phosphate 4-epimerase resulting in Xylulose 5-phosphate. This compound can then be part of the pentose phosphate pathway. Expression of the ula regulon is regulated by the L-ascorbate 6-phosphate-binding repressor UlaR and by cAMP-CRP. Under aerobic conditions, metabolism of L-ascorbate is hindered by the special reactivity and toxicity of this compound in the presence of oxygen. PW000793 Metabolic L-ascorbate degradation II (bacterial, aerobic) PWY-6961 L-ascorbate degradation I (bacterial, anaerobic) PWY0-301 Specdb::MsMs 23000 Specdb::MsMs 23001 Specdb::MsMs 23002 Specdb::MsMs 29798 Specdb::MsMs 29799 Specdb::MsMs 29800 393 384 CPD-2343 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 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 L-xylulose/3-keto-L-gulonate kinase P37677 LYXK_ECOLI lyx http://ecmdb.ca/proteins/P37677.xml 3-keto-L-gulonate-6-phosphate decarboxylase sgbH P37678 SGBH_ECOLI sgbH http://ecmdb.ca/proteins/P37678.xml 3-keto-L-gulonate-6-phosphate decarboxylase ulaD P39304 ULAD_ECOLI ulaD http://ecmdb.ca/proteins/P39304.xml Probable L-ascorbate-6-phosphate lactonase ulaG P39300 ULAG_ECOLI ulaG http://ecmdb.ca/proteins/P39300.xml L-ascorbate 6-phosphate + Water + L-Ascorbate 6-phosphate > 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate PW_R002696 3-Dehydro-L-gulonate + Adenosine triphosphate > 3-keto-L-gulonate 6-phosphate + Adenosine diphosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate + ADP PW_R002697 3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > Xylulose 5-phosphate + Carbon dioxide + Xylulose 5-phosphate PW_R002703 3-keto-L-gulonate 6-phosphate + Hydrogen ion + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + Carbon dioxide + L-Xylulose 5-phosphate PW_R002712 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate > L-xylulose -5-phosphate + L-Xylulose 5-phosphate PW_R002711