2.02012-05-31 14:07:52 -06002015-09-13 12:56:14 -0600ECMDB06236M2MDB000661PhenylacetaldehydePhenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. (PMID: 16910727, 7818768, 15606130).alpha.-toluic aldehyde1-Oxo-2-phenylethane2-Phenylacetaldehyde2-PhenylethanalA-PhenylacetaldehydeA-TolualdehydeA-Toluic aldehydeAlpha-PhenylacetaldehydeAlpha-TolualdehydeAlpha-Toluic aldehydeBenzenacetaldehydeBenzeneacetaldehydeBenzylcarboxaldehydeFEMA No. 2974HyacinthinOxophenylethanePhenacetaldehydePhenyl-AcetaldehydePhenylacetaldehydePhenylacetic aldehydePhenylethanalα-Phenylacetaldehydeα-Tolualdehydeα-Toluic aldehydeC8H8O120.1485120.0575148782-phenylacetaldehydephenylacetaldehyde122-78-1O=CCC1=CC=CC=C1InChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2DTUQWGWMVIHBKE-UHFFFAOYSA-NSolidCytosolExtra-organismPeriplasmlogp1.75logs-1.76solubility2.08e+00 g/lmelting_point120.5-121.5 oClogp1.45pka_strongest_acidic14.98pka_strongest_basic-7iupac2-phenylacetaldehydeaverage_mass120.1485mono_mass120.057514878smilesO=CCC1=CC=CC=C1formulaC8H8OinchiInChI=1S/C8H8O/c9-7-6-8-4-2-1-3-5-8/h1-5,7H,6H2inchikeyDTUQWGWMVIHBKE-UHFFFAOYSA-Npolar_surface_area17.07refractivity36.44polarizability12.91rotatable_bond_count2acceptor_count1donor_count0physiological_charge0formal_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.PW000921ec00360MetabolicStyrene degradationec00643Microbial metabolism in diverse environmentsec01120Metabolic pathwayseco01100Phenylethylamine metabolismThe process of phenylethylamine metabolism starts with 2-phenylethylamine interacting with an oxygen molecule and a water molecule in the periplasmic space through a phenylethylamine oxidase. This reaction results in the release of a hydrogen peroxide, ammonium and phenylacetaldehyde.
Phenylacetaldehyde is introduced into the cytosol and degraded into phenylacetate by reaction with a phenylacetaldehyde dehydrogenase. This reaction involves phenylacetaldehyde interacting with NAD, and a water molecule and then resulting in the release of NADH, and 2 hydrogen ion.
Phenylacetate is then degraded. The first step involves phenylacetate interacting with an coenzyme A and an ATP driven phenylacetate-CoA ligase resulting in the release of a AMP, a diphosphate and a phenylacetyl-CoA. This resulting compound the interacts with a hydrogen ion, NADPH, and oxygen molecule through a ring 1,2-phenylacetyl-CoA epoxidase protein complex resulting in the release of a water molecule, an NADP and a 2-(1,2-epoxy-1,2-dihydrophenyl)acetyl-CoA. This compound is then metabolized by a ring 1,2 epoxyphenylacetyl-CoA isomerase resulting in a 2-oxepin-2(3H)-ylideneacetyl-CoA. This compound is then hydrolated through a oxepin-CoA hydrolase resulting in a 3-oxo-5,6-didehydrosuberyl-CoA semialdehyde. This commpound then interacts with a water molecule and NADP driven 3-oxo-5,6-dehydrosuberyl-CoA semialadehyde dehydrogenase resulting in 2 hydrogen ions, a NADPH and a 3-oxo-5,6-didehydrosuberyl-CoA. The resulting compound interacts with a coenzyme A and a 3-oxo-5,6 dehydrosuberyl-CoA thiolase resulting in an acetyl-CoA and a 2,3-didehydroadipyl-CoA. This resulting compound is the hydrated by a 2,3-dehydroadipyl-CoA hydratas resulting in a 3-hydroxyadipyl-CoA whuch is dehydrogenated through an NAD driven 3-hydroxyadipyl-CoA dehydrogenase resulting in a NADH, a hydrogen ion and a 3-oxoadipyl-CoA. The latter compound then interacts with conezyme A through a beta-ketoadipyl-CoA thiolase resulting in an acetyl-CoA and a succinyl-CoA. The succinyl-CoA is then integrated into the TCA cycle.PW002027Metabolicphenylethylamine degradation I2PHENDEG-PWYSpecdb::CMs954Specdb::CMs960Specdb::CMs3424Specdb::CMs29540Specdb::CMs31533Specdb::CMs31534Specdb::CMs32185Specdb::CMs32186Specdb::CMs32208Specdb::CMs32209Specdb::CMs32210Specdb::CMs32211Specdb::CMs135391Specdb::CMs143125Specdb::EiMs671Specdb::NmrOneD67932Specdb::NmrOneD67933Specdb::NmrOneD67934Specdb::NmrOneD67935Specdb::NmrOneD67936Specdb::NmrOneD67937Specdb::NmrOneD67938Specdb::NmrOneD67939Specdb::NmrOneD67940Specdb::NmrOneD67941Specdb::NmrOneD67942Specdb::NmrOneD67943Specdb::NmrOneD67944Specdb::NmrOneD67945Specdb::NmrOneD67946Specdb::NmrOneD67947Specdb::NmrOneD67948Specdb::NmrOneD67949Specdb::NmrOneD67950Specdb::NmrOneD67951Specdb::MsMs2478Specdb::MsMs2479Specdb::MsMs2480Specdb::MsMs6106Specdb::MsMs7760Specdb::MsMs7761Specdb::MsMs7762Specdb::MsMs14432Specdb::MsMs14433Specdb::MsMs14434Specdb::MsMs2251780Specdb::MsMs2397450Specdb::MsMs2397451Specdb::MsMs2397452Specdb::MsMs2541254Specdb::MsMs2541255Specdb::MsMs2541256HMDB0623699813876539C0060116424PHENYLACETALDEHYDEHY1PAAKeseler, 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 80:2939-2948.18331064Cho, I. H., Kim, S. Y., Choi, H. K., Kim, Y. S. (2006). "Characterization of aroma-active compounds in raw and cooked pine-mushrooms (Tricholoma matsutake Sing.)." J Agric Food Chem 54:6332-6335.16910727Watson WP, Munter T, Golding BT: A new role for glutathione: protection of vitamin B12 from depletion by xenobiotics. Chem Res Toxicol. 2004 Dec;17(12):1562-7.15606130Sumner SJ, Fennell TR: Review of the metabolic fate of styrene. Crit Rev Toxicol. 1994;24 Suppl:S11-33.7818768Sun Zhirong; Hu Xiang; Zhou Ding Wastewater minimization in indirect electrochemical synthesis of phenylacetaldehyde. TheScientificWorldJournal (2002), 2 48-52. http://hmdb.ca/system/metabolites/msds/000/005/361/original/HMDB06236.pdf?1358462404Primary amine oxidaseP46883AMO_ECOLItynAhttp://ecmdb.ca/proteins/P46883.xmlPhenylacetaldehyde dehydrogenaseP80668FEAB_ECOLIfeaBhttp://ecmdb.ca/proteins/P80668.xmlOuter membrane protein NP77747OMPN_ECOLIompNhttp://ecmdb.ca/proteins/P77747.xmlOuter membrane pore protein EP02932PHOE_ECOLIphoEhttp://ecmdb.ca/proteins/P02932.xmlOuter membrane protein FP02931OMPF_ECOLIompFhttp://ecmdb.ca/proteins/P02931.xmlOuter membrane protein CP06996OMPC_ECOLIompChttp://ecmdb.ca/proteins/P06996.xmlWater + NAD + Phenylacetaldehyde <>2 Hydrogen ion + NADH + Benzeneacetic acidR02536Water + Oxygen + Phenylethylamine > Hydrogen peroxide + Ammonium + PhenylacetaldehydePhenylacetaldehyde + NAD + Water <> Benzeneacetic acid + NADH + Hydrogen ionR02536Phenylethylamine + Oxygen + Water <> Phenylacetaldehyde + Ammonia + Hydrogen peroxideR02613Water + Oxygen + Phenylethylamine > Hydrogen ion + Hydrogen peroxide + Ammonia + PhenylacetaldehydeR02613AMINEPHEN-RXNWater + NAD + Phenylacetaldehyde <> Hydrogen ion + NADH + phenylacetatePHENDEHYD-RXNPhenylethylamine + Water + Oxygen > Phenylacetaldehyde + Ammonia + Hydrogen peroxidePhenylacetaldehyde + NAD + Water > Benzeneacetic acid + NADHPhenylacetaldehyde + NAD + Water > NADH + Hydrogen ion + Benzeneacetic acidPW_R005918