2.02012-05-31 14:03:57 -06002015-06-03 15:54:41 -0600ECMDB04061M2MDB0005913-(2,3-Dihydroxyphenyl)propionic acid3-(2,3-dihydroxyphenyl)propionate is a member of the chemical class known as Catechols. These are compounds containing a 1,2-benzenediol moeity. 3-(2,3-dihydroxyphenyl)propionate is invovled in Phenylalanine metabolism, Microbial metabolism in diverse environments, and Phenylpropionic acid degradation. The compound 3-(2,3-dihydroxyphenyl)propionate (DHPP) is a common intermediate of both pathways which must be cleaved by the MhpB dioxygenase before entering into the primary cell metabolism. (PMID 19520845)2,3-DHP2,3-Dihydroxyphenylpropanoate2,3-Dihydroxyphenylpropanoic acid3-(2,3-Dihydroxyphenyl)propanoate3-(2,3-Dihydroxyphenyl)propanoic acid3-(2,3-Dihydroxyphenyl)propionate3-(2,3-Dihydroxyphenyl)propionic acid3-(2,3-Hihydroxyphenyl)propanoate3-(2,3-Hihydroxyphenyl)propanoic acid3-CarboxyethylcatecholC9H9O4181.1654181.0500837763-(2-carboxyethyl)-2-hydroxybenzen-1-olate3-(2-carboxyethyl)-2-hydroxybenzenolateOC(=O)CCC1=C(O)C([O-])=CC=C1InChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)/p-1QZDSXQJWBGMRLU-UHFFFAOYSA-MCytosollogp0.87logs-1.11solubility1.55e+01 g/llogp1.45pka_strongest_acidic3.84pka_strongest_basic-6.3iupac3-(2-carboxyethyl)-2-hydroxybenzen-1-olateaverage_mass181.1654mono_mass181.050083776smilesOC(=O)CCC1=C(O)C([O-])=CC=C1formulaC9H9O4inchiInChI=1S/C9H10O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,10,13H,4-5H2,(H,11,12)/p-1inchikeyQZDSXQJWBGMRLU-UHFFFAOYSA-Mpolar_surface_area80.59refractivity56.48polarizability17.31rotatable_bond_count3acceptor_count4donor_count2physiological_charge-1formal_charge-1Phenylalanine metabolismThe pathways of the metabolism of phenylalaline begins with the conversion of chorismate to prephenate through a P-protein (chorismate mutase:pheA). Prephenate then interacts with a hydrogen ion through the same previous enzyme resulting in a release of carbon dioxide, water and a phenolpyruvic acid. Three enzymes those enconde by tyrB, aspC and ilvE are involved in catalyzing the third step of these pathways, all three can contribute to the synthesis of phenylalanine: only tyrB and aspC contribute to biosynthesis of tyrosine.
Phenolpyruvic acid can also be obtained from a reversivle reaction with ammonia, a reduced acceptor and a D-amino acid dehydrogenase, resulting in a water, an acceptor and a D-phenylalanine, which can be then transported into the periplasmic space by aromatic amino acid exporter.
L-phenylalanine also interacts in two reversible reactions, one involved with oxygen through a catalase peroxidase resulting in a carbon dioxide and 2-phenylacetamide. The other reaction involved an interaction with oxygen through a phenylalanine aminotransferase resulting in a oxoglutaric acid and phenylpyruvic acid.
L-phenylalanine can be imported into the cytoplasm through an aromatic amino acid:H+ symporter AroP.
The compound can also be imported into the periplasmic space through a transporter: L-amino acid efflux transporter.PW000921ec00360MetabolicMicrobial metabolism in diverse environmentsec011202-Oxopent-4-enoate metabolismThe pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate.
The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate.
The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW001890Metabolic2-Oxopent-4-enoate metabolism 2The pathway starts with trans-cinnamate interacting with a hydrogen ion, an oxygen molecule, and a NADH through a cinnamate dioxygenase resulting in a NAD and a Cis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol which then interact together through a 2,3-dihydroxy-2,3-dihydrophenylpropionate dehydrogenase resulting in the release of a hydrogen ion, an NADH molecule and a 2,3 dihydroxy-trans-cinnamate. The second way by which the 2,3 dihydroxy-trans-cinnamate is acquired is through a 3-hydroxy-trans-cinnamate interacting with a hydrogen ion, a NADH and an oxygen molecule through a 3-(3-hydroxyphenyl)propionate 2-hydroxylase resulting in the release of a NAD molecule, a water molecule and a 2,3-dihydroxy-trans-cinnamate. The compound 2,3 dihydroxy-trans-cinnamate then interacts with an oxygen molecule through a 2,3-dihydroxyphenylpropionate 1,2-dioxygenase resulting in a hydrogen ion and a 2-hydroxy-6-oxonona-2,4,7-triene-1,9-dioate. The latter compound then interacts with a water molecule through a 2-hydroxy-6-oxononatrienedioate hydrolase resulting in a release of a hydrogen ion, a fumarate molecule and (2Z)-2-hydroxypenta-2,4-dienoate. The latter compound reacts spontaneously to isomerize into a 2-oxopent-4-enoate. This compound is then hydrated through a 2-oxopent-4-enoate hydratase resulting in a 4-hydroxy-2-oxopentanoate. This compound then interacts with a 4-hydroxy-2-ketovalerate aldolase resulting in the release of a pyruvate, and an acetaldehyde. The acetaldehyde then interacts with a coenzyme A and a NAD molecule through a acetaldehyde dehydrogenase resulting in a hydrogen ion, a NADH and an acetyl-coa which can be incorporated into the TCA cyclePW002035Metabolic3-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoateHCAMHPDEG-PWYSpecdb::NmrOneD288655Specdb::NmrOneD288656Specdb::NmrOneD288657Specdb::NmrOneD288658Specdb::NmrOneD288659Specdb::NmrOneD288660Specdb::NmrOneD288661Specdb::NmrOneD288662Specdb::NmrOneD288663Specdb::NmrOneD288664Specdb::NmrOneD288665Specdb::NmrOneD288666Specdb::NmrOneD288667Specdb::NmrOneD288668Specdb::NmrOneD288669Specdb::NmrOneD288670Specdb::NmrOneD288671Specdb::NmrOneD288672Specdb::NmrOneD288673Specdb::NmrOneD288674Specdb::MsMs27842Specdb::MsMs27843Specdb::MsMs27844Specdb::MsMs34400Specdb::MsMs34401Specdb::MsMs3440295431237822096C04044469512-3-DIHYDROXYPHENYL-PROPIONATEKeseler, 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 80:2939-2948.18331064Manso, I., Torres, B., Andreu, J. M., Menendez, M., Rivas, G., Alfonso, C., Diaz, E., Garcia, J. L., Galan, B. (2009). "3-Hydroxyphenylpropionate and phenylpropionate are synergistic activators of the MhpR transcriptional regulator from Escherichia coli." J Biol Chem 284:21218-21228.195208452,3-dihydroxyphenylpropionate/2,3-dihydroxicinnamic acid 1,2-dioxygenaseP0ABR9MHPB_ECOLImhpBhttp://ecmdb.ca/proteins/P0ABR9.xml3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenaseP0CI31hcaBhttp://ecmdb.ca/proteins/P0CI31.xml3-(3-hydroxy-phenyl)propionate/3-hydroxycinnamic acid hydroxylaseP77397MHPA_ECOLImhpAhttp://ecmdb.ca/proteins/P77397.xml3-(3-Hydroxyphenyl)propanoic acid + Hydrogen ion + NADH + Oxygen > 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR067863-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > Hydrogen ion + 2-Hydroxy-6-ketononadienedicarboxylateR043761.13.11.16-RXNCis-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propionic acid + Hydrogen ion + NADH3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen <> 2-Hydroxy-6-ketononadienedicarboxylateR04376cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ionR06784PHENPRODIOLDEHYDROG-RXN3-(3-Hydroxyphenyl)propanoic acid + Oxygen + NADH + Hydrogen ion <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NADR06786Hydrogen ion + 3-(3-Hydroxyphenyl)propionate + NADH + Oxygen > Water + 3-(2,3-Dihydroxyphenyl)propionic acid + NADMHPHYDROXY-RXNcis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > Hydrogen ion + 3-(2,3-Dihydroxyphenyl)propionic acid + NADHPHENPRODIOLDEHYDROG-RXN3-(3-Hydroxyphenyl)propanoic acid + NADH + Hydrogen ion + Oxygen + 3-Hydroxycinnamic acid <> 3-(2,3-Dihydroxyphenyl)propionic acid + Water + NAD + Trans-2,3-DihydroxycinnamateR06786 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen + Trans-2,3-Dihydroxycinnamate <> 2-Hydroxy-6-ketononadienedicarboxylate + 2-Hydroxy-6-ketononatrienedioateR04376 cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + cis-3-(3-Carboxyethenyl)-3,5-cyclohexadiene-1,2-diol <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ion + Trans-2,3-DihydroxycinnamateR06784 3-(2,3-Dihydroxyphenyl)propionic acid + Oxygen > (2E,4Z)-2-hydroxy-6-oxonona-2,4-diene-1,9-dioate + Hydrogen ionPW_R005882