2.0 2012-05-31 14:30:53 -0600 2015-09-17 15:41:58 -0600 ECMDB20164 M2MDB001011 L-Ascorbate 6-phosphate L-ascorbate 6-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. L-Ascorbic acid 6-phosphate L-Ascorbic acid 6-phosphoric acid C6H6O9P 253.08 252.976589511 [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy]phosphonic acid L-ascorbyl phosphate [H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1 KIENGQUGHPTFGC-JLAZNSOCSA-K Cytosol logp -1.54 ALOGPS logs -1.21 ALOGPS solubility 1.59e+01 g/l ALOGPS logp -2 ChemAxon pka_strongest_acidic 1.48 ChemAxon pka_strongest_basic -3.6 ChemAxon iupac [(2S)-2-[(2R)-3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl]-2-hydroxyethoxy]phosphonic acid ChemAxon average_mass 253.08 ChemAxon mono_mass 252.976589511 ChemAxon smiles [H][C@@]1(OC(=O)C(O)=C1[O-])[C@@H](O)COP([O-])([O-])=O ChemAxon formula C6H6O9P ChemAxon inchi InChI=1S/C6H9O9P/c7-2(1-14-16(11,12)13)5-3(8)4(9)6(10)15-5/h2,5,7-9H,1H2,(H2,11,12,13)/p-3/t2-,5+/m0/s1 ChemAxon inchikey KIENGQUGHPTFGC-JLAZNSOCSA-K ChemAxon polar_surface_area 153.75 ChemAxon refractivity 47.9 ChemAxon polarizability 19.59 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Ascorbate and aldarate metabolism ec00053 Phosphotransferase system (PTS) ec02060 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 I (bacterial, anaerobic) PWY0-301 Specdb::MsMs 25121 Specdb::MsMs 25122 Specdb::MsMs 25123 Specdb::MsMs 31679 Specdb::MsMs 31680 Specdb::MsMs 31681 23724654 C16186 L-ASCORBATE-6-PHOSPHATE 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 Phosphoenolpyruvate-protein phosphotransferase P08839 PT1_ECOLI ptsI http://ecmdb.ca/proteins/P08839.xml Putative phosphotransferase enzyme IIA component yadI P36881 YADI_ECOLI yadI http://ecmdb.ca/proteins/P36881.xml Ascorbate-specific phosphotransferase enzyme IIA component P69820 ULAC_ECOLI ulaC http://ecmdb.ca/proteins/P69820.xml Ascorbate-specific phosphotransferase enzyme IIB component P69822 ULAB_ECOLI ulaB http://ecmdb.ca/proteins/P69822.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Probable L-ascorbate-6-phosphate lactonase ulaG P39300 ULAG_ECOLI ulaG http://ecmdb.ca/proteins/P39300.xml Phosphocarrier protein HPr P0AA04 PTHP_ECOLI ptsH http://ecmdb.ca/proteins/P0AA04.xml Ascorbate-specific permease IIC component ulaA P39301 ULAA_ECOLI ulaA http://ecmdb.ca/proteins/P39301.xml Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate + Hydrogen ion R07677 RXN0-5214 Protein N(pi)-phospho-L-histidine + Ascorbic acid <> Protein histidine + L-Ascorbate 6-phosphate R07671 L-Ascorbate 6-phosphate + Water <> 3-Dehydro-L-gulonate 6-phosphate R07677 RXN0-5214 Phosphoenolpyruvic acid + Ascorbic acid > L-Ascorbate 6-phosphate + Pyruvic acid RXN0-2461 L-Ascorbate 6-phosphate + Water > 3-Dehydro-L-gulonate 6-phosphate RXN0-5214 L-ascorbate 6-phosphate + Water + L-Ascorbate 6-phosphate > 3-keto-L-gulonate 6-phosphate + 3-Keto-L-gulonate 6-phosphate PW_R002696 Ascorbic acid + HPr - phosphorylated + Ascorbic acid > L-ascorbate 6-phosphate + HPr + L-Ascorbate 6-phosphate PW_RCT000136