2.02012-05-31 14:29:05 -06002015-06-03 17:19:22 -0600ECMDB20130M2MDB000978cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolCis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol (also known as 3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate) is an intermediate invovled in Phenylpropionic acid degradation. It is a substrate for the enzyme 3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenase (hcaB). This enzyme normally converts 3-phenylpropionate-dihydrodiol (PP-dihydrodiol) and cinnamic acid-dihydrodiol (CI-dihydrodiol) into 3-(2,3-dihydroxylphenyl)propanoic acid (DHPP) and 2,3-dihydroxicinnamic acid (DHCI), respectively. Cis-3-(carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol is also a substrate for 3-phenylpropionate/cinnamic acid dioxygenase (hcaE and hcaF), which is also part of the phentylpropionic acid degradatioin pathway. This enzyme catalyzes the reaction 3-phenylpropanoate + NADH + O2 = 3-(cis-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate + NAD+3-(<i>cis</i>-5,6-dihydroxycyclohexa-1,3-dien-1-yl)propanoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoate3-(cis-5,6-Dihydroxycyclohexa-1,3-dien-1-yl)propanoic acid3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoate3-[(5S,6R)-5,6-Dihydroxycyclohexa-1,3-dienyl]propanoic acid<i>cis</i>-3-(3-carboxyethyl)-3,5-cyclohexadiene-1,2-diol<i>cis</i>-3-(carboxyethyl)-3,5-cyclohexadiene-1,2-diolCis-3-(2-Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolCis-3-(2-Carboxyethyl)-3,5-cyclohexadiene-1,2-diolCis-3-(3-Carboxyethyl)-3,5-cyclohexadiene-1,2-diolCis-3-(Carboxyethyl)-3,5-cyclohexadiene-1,2-diolC9H12O4184.1892184.0735588723-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acid[H][C@]1(O)C=CC=C(CCC(O)=O)[C@@]1([H])OInChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/t7-,9+/m0/s1RKDFGWAXBBGKMR-IONNQARKSA-NCytosollogp-0.14logs-0.74solubility3.36e+01 g/llogp-0.39pka_strongest_acidic4.38pka_strongest_basic-3.3iupac3-[(5S,6R)-5,6-dihydroxycyclohexa-1,3-dien-1-yl]propanoic acidaverage_mass184.1892mono_mass184.073558872smiles[H][C@]1(O)C=CC=C(CCC(O)=O)[C@@]1([H])OformulaC9H12O4inchiInChI=1S/C9H12O4/c10-7-3-1-2-6(9(7)13)4-5-8(11)12/h1-3,7,9-10,13H,4-5H2,(H,11,12)/t7-,9+/m0/s1inchikeyRKDFGWAXBBGKMR-IONNQARKSA-Npolar_surface_area77.76refractivity47.71polarizability18.16rotatable_bond_count3acceptor_count4donor_count3physiological_charge-1formal_charge0Phenylalanine 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 environmentsec011203-phenylpropionate and 3-(3-hydroxyphenyl)propionate degradation to 2-oxopent-4-enoateHCAMHPDEG-PWYSpecdb::CMs1084302Specdb::EiMs2680Specdb::NmrOneD314581Specdb::NmrOneD314582Specdb::NmrOneD314583Specdb::NmrOneD314584Specdb::NmrOneD314585Specdb::NmrOneD314586Specdb::NmrOneD314587Specdb::NmrOneD314588Specdb::NmrOneD314589Specdb::NmrOneD314590Specdb::NmrOneD314591Specdb::NmrOneD314592Specdb::NmrOneD314593Specdb::NmrOneD314594Specdb::NmrOneD314595Specdb::NmrOneD314596Specdb::NmrOneD314597Specdb::NmrOneD314598Specdb::NmrOneD314599Specdb::NmrOneD314600Specdb::MsMs25754Specdb::MsMs25755Specdb::MsMs25756Specdb::MsMs32312Specdb::MsMs32313Specdb::MsMs32314443290391536C1158810472CARBOXYETHYL-3-5-CYCLOHEXADIENE-1-2-DIOLKeseler, 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-D114.22080510Winder, 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 80:2939-2948.18331064Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A3-phenylpropionate/cinnamic acid dioxygenase subunit alphaP0ABR5HCAE_ECOLIhcaEhttp://ecmdb.ca/proteins/P0ABR5.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin subunitP0ABW0HCAC_ECOLIhcaChttp://ecmdb.ca/proteins/P0ABW0.xml3-phenylpropionate/cinnamic acid dioxygenase ferredoxin--NAD(+) reductase componentP77650HCAD_ECOLIhcaDhttp://ecmdb.ca/proteins/P77650.xml3-phenylpropionate/cinnamic acid dioxygenase subunit betaQ47140HCAF_ECOLIhcaFhttp://ecmdb.ca/proteins/Q47140.xml3-phenylpropionate-dihydrodiol/cinnamic acid-dihydrodiol dehydrogenaseP0CI31hcaBhttp://ecmdb.ca/proteins/P0CI31.xmlHydrocinnamic acid + Oxygen + NADH + Hydrogen ion <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADR06782HCAMULTI-RXNcis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD <> 3-(2,3-Dihydroxyphenyl)propionic acid + NADH + Hydrogen ionR06784PHENPRODIOLDEHYDROG-RXNHydrocinnamic acid + NADH + Oxygen + Hydrogen ion > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADHCAMULTI-RXNcis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > Hydrogen ion + 3-(2,3-Dihydroxyphenyl)propionic acid + NADHPHENPRODIOLDEHYDROG-RXNcis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD > 3-(2,3-Dihydroxyphenyl)propanoate + NADHHydrocinnamic acid + NADH + Oxygen > cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NADR06782HCAMULTI-RXNNADH + Hydrogen ion + Oxygen + Hydrocinnamic acid <> cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diol + NAD + Trans-2,3-DihydroxycinnamateR06782 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 NADH + Oxygen + 3-phenylpropanoate <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolPW_R003836Hydrocinnamic acid + NADH + Oxygen <> NAD + cis-3-(Carboxy-ethyl)-3,5-cyclo-hexadiene-1,2-diolPW_R003850