2.02012-05-31 14:31:58 -06002015-09-17 15:42:09 -0600ECMDB20184M2MDB001030Propanoyl phosphatePropanoyl phosphate is an alkylphosphate. It is generated during the course of threonine degradation via propanoyl-CoA. The first reaction in the anaerobic threonine dehydratase pathway is catalyzed by catabolic threonine dehydratase which degrades threonine to 2-oxobutanoate (alpha-ketobutyrate) and ammonia. The 2-oxobutanoate then undergoes lyase cleavage with the addition of coenzyme A to form propanoyl-CoA and formate. Once propanoyl-CoA is formed, it is processed via propionyl-phosphate to propionate in a reaction sequence that produces ATP. Acetate kinase AckA can also utilize propionate as a substrate in the final reaction. The enzymes in this pathway are also able to process L-serine, with pyruvate as the final product [EcoCyc].Propanoyl phosphoric acidPropanoyl-PPropionyl phosphatePropionyl phosphoric acidPropionyl-PPropionyl-phosphatePropionyl-phosphoric acidC3H5O5P152.043151.988557419(propanoyloxy)phosphonic acidpropionyl phosphate121-69-7CCC(=O)OP([O-])([O-])=OInChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2FMNMEQSRDWIBFO-UHFFFAOYSA-LSolidCytosollogp-0.32logs-0.88solubility2.01e+01 g/lmelting_point2.5 oClogp-0.18pka_strongest_acidic1.23pka_strongest_basic-7.4iupac(propanoyloxy)phosphonic acidaverage_mass152.043mono_mass151.988557419smilesCCC(=O)OP([O-])([O-])=OformulaC3H5O5PinchiInChI=1S/C3H7O5P/c1-2-3(4)8-9(5,6)7/h2H2,1H3,(H2,5,6,7)/p-2inchikeyFMNMEQSRDWIBFO-UHFFFAOYSA-Lpolar_surface_area83.83refractivity28.43polarizability11.82rotatable_bond_count3acceptor_count4donor_count2physiological_charge-2formal_charge0C5-Branched dibasic acid metabolismec00660Propanoate metabolism
Starting from L-threonine, this compound is deaminated through a threonine deaminase resulting in a hydrogen ion, a water molecule and a (2z)-2-aminobut-2-enoate. The latter compound then isomerizes to a 2-iminobutanoate, This compound then reacts spontaneously with hydrogen ion and a water molecule resulting in a ammonium and a 2-Ketobutyric acid. The latter compound interacts with CoA through a pyruvate formate-lyase / 2-ketobutyrate formate-lyase resulting in a formic acid and a propionyl-CoA.
Propionyl-CoA can then be processed either into a 2-methylcitric acid or into a propanoyl phosphate.
Propionyl-CoA interacts with oxalacetic acid and a water molecule through a 2-methylcitrate synthase resulting in a hydrogen ion, a CoA and a 2-Methylcitric acid.The latter compound is dehydrated through a 2-methylcitrate dehydratase resulting in a water molecule and cis-2-methylaconitate. The latter compound is then dehydrated by a
bifunctional aconitate hydratase 2 and 2-methylisocitrate dehydratase resulting in a water molecule and methylisocitric acid. The latter compound is then processed by 2-methylisocitrate lyase resulting in a release of succinic acid and pyruvic acid.
Succinic acid can then interact with a propionyl-CoA through a propionyl-CoA:succinate CoA transferase resulting in a propionic acid and a succinyl CoA. Succinyl-CoA is then isomerized through a methylmalonyl-CoA mutase resulting in a methylmalonyl-CoA. This compound is then decarboxylated through a methylmalonyl-CoA decarboxylase resulting in a release of Carbon dioxide and Propionyl-CoA.
ropionyl-CoA interacts with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate.
Propionyl-CoA can react with a phosphate through a phosphate acetyltransferase / phosphate propionyltransferase resulting in a CoA and a propanoyl phosphate. The latter compound is then dephosphorylated through a ADP driven acetate kinase/propionate kinase protein complex resulting in an ATP and Propionic acid.
Propionic acid can be processed by a reaction with CoA through a ATP-driven propionyl-CoA synthetase resulting in a pyrophosphate, an AMP and a propionyl-CoA.PW000940ec00640Metabolicthreonine degradation IPWY-5437Specdb::MsMs25523Specdb::MsMs25524Specdb::MsMs25525Specdb::MsMs32081Specdb::MsMs32082Specdb::MsMs3208310341007C0287616269PROPIONYL-PKeseler, 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 370:17-25.17765195Acetate kinaseP0A6A3ACKA_ECOLIackAhttp://ecmdb.ca/proteins/P0A6A3.xmlPhosphate acetyltransferaseP0A9M8PTA_ECOLIptahttp://ecmdb.ca/proteins/P0A9M8.xmlPropionate kinaseP11868TDCD_ECOLItdcDhttp://ecmdb.ca/proteins/P11868.xmlPhosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphateR00921PTAALT-RXNADP + Propanoyl phosphate <> Adenosine triphosphate + Propionic acidR01353PROPKIN-RXNPropionyl-CoA + Phosphate <> Propanoyl phosphate + Coenzyme AR00921Adenosine triphosphate + Propionic acid <> ADP + Propanoyl phosphateR01353Adenosine triphosphate + Propionic acid > ADP + Propanoyl phosphatePropionyl-CoA + Phosphate + Propionyl-CoA > Coenzyme A + propanoyl phosphate + Propanoyl phosphatePW_R003494Adenosine diphosphate + propanoyl phosphate + ADP + Propanoyl phosphate > Adenosine triphosphate + Propionic acidPW_R003495Phosphate + Propionyl-CoA > Coenzyme A + Propanoyl phosphate