2.02012-05-31 13:56:51 -06002015-06-03 15:54:17 -0600ECMDB02654M2MDB000461PhenylethylaminePhenethylamine is an aromatic amine, which is a colorless liquid at room temperature. It is also known as 2-phenylethylamine, and is an alkaloid and monoamine. Phenethylamine also has a constitutional isomer 1-phenylethylamine. (HMDB) In E. coli phenylalanine metabolism, 2-phenylethylamine can be degraded to phenylacetaldehyde in a reversible reaction catalyzed by a primary-amine oxidase (EC:1.4.3.21). (KEGG)β-phenylethylamine(2-Aminoethyl)benzene(2-Aminoethyl)polystyrene1-Amino-2-phenylethane1-Phenethylamine1-Phenyl-2-amino-athan1-Phenyl-2-amino-athan (GERMAN)1-Phenyl-2-amino-athan [German]1-Phenyl-2-aminoethane1tnj1utm1uto2-Amino-1-phenylethane2-Amino-fenylethan2-Amino-fenylethan [Czech]2-Fenylethylamin2-Fenylethylamin [Czech]2-Phenethylamine2-Phenyl-Ethanamine2-Phenylethanamine2-phenylethanamine (ACD/Name 4.0)2-Phenylethylamine2-phenylethylamine (ACD/Name 4.0)b PhenethylamineB-AminoethylbenzeneB-PhenethylamineB-PhenylaethylaminB-Phenylaethylamin (german)b-Phenylaethylamin [german]B-PhenylethylamineBenzeneethanamineBenzeneethanamine hydrochlorideBeta PhenethylamineBeta-AminoethylbenzeneBeta-PhenethylamineBeta-PhenylaethylaminBeta-phenylaethylamin (german)Beta-Phenylaethylamin [german]Beta-PhenylethylamineOmega-phenylethylaminePEAPhenethylaminePhenethylamine hydrochloridePhenylethylaminePolystyrene A-NH2β Phenethylamineβ-Aminoethylbenzeneβ-Phenethylamineβ-Phenylaethylaminβ-Phenylaethylamin (german)β-Phenylaethylamin [german]β-PhenylethylamineC8H11N121.1796121.0891493572-phenylethan-1-amine2-phenylethylamine64-04-0NCCC1=CC=CC=C1InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2BHHGXPLMPWCGHP-UHFFFAOYSA-NSolidExtra-organismPeriplasmlogp1.41logs-1.74solubility2.19e+00 g/llogp1.39pka_strongest_basic9.79iupac2-phenylethan-1-amineaverage_mass121.1796mono_mass121.089149357smilesNCCC1=CC=CC=C1formulaC8H11NinchiInChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2inchikeyBHHGXPLMPWCGHP-UHFFFAOYSA-Npolar_surface_area26.02refractivity39.29polarizability14.35rotatable_bond_count2acceptor_count1donor_count1physiological_charge1formal_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.PW000921ec00360MetabolicPhenylethylamine 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::CMs1044Specdb::CMs1248Specdb::CMs3027Specdb::CMs27376Specdb::CMs28073Specdb::CMs28122Specdb::CMs29046Specdb::CMs29532Specdb::CMs31563Specdb::CMs31564Specdb::CMs32178Specdb::CMs146217Specdb::EiMs1837Specdb::NmrOneD3950Specdb::NmrOneD4232Specdb::NmrOneD5052Specdb::NmrOneD5053Specdb::NmrOneD96898Specdb::NmrOneD96899Specdb::NmrOneD96900Specdb::NmrOneD96901Specdb::NmrOneD96902Specdb::NmrOneD96903Specdb::NmrOneD96904Specdb::NmrOneD96905Specdb::NmrOneD96906Specdb::NmrOneD96907Specdb::NmrOneD96908Specdb::NmrOneD96909Specdb::NmrOneD96910Specdb::NmrOneD96911Specdb::NmrOneD96912Specdb::NmrOneD96913Specdb::NmrOneD96914Specdb::NmrOneD96915Specdb::NmrOneD96916Specdb::NmrOneD96917Specdb::MsMs441452Specdb::MsMs446752Specdb::MsMs446753Specdb::MsMs446754Specdb::MsMs446755Specdb::MsMs446756Specdb::MsMs446807Specdb::MsMs446808Specdb::MsMs446809Specdb::MsMs446810Specdb::MsMs446811Specdb::MsMs448397Specdb::MsMs448398Specdb::MsMs448399Specdb::MsMs448400Specdb::MsMs448401Specdb::MsMs448402Specdb::MsMs448403Specdb::MsMs448404Specdb::MsMs448405Specdb::MsMs448406Specdb::MsMs448407Specdb::MsMs448408Specdb::MsMs448409Specdb::MsMs448410HMDB12275100113856352C0533218397PHENYLETHYLAMINEPEAPhenylethylamineKeseler, 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 80:2939-2948.18331064Kusaga A, Yamashita Y, Koeda T, Hiratani M, Kaneko M, Yamada S, Matsuishi T: Increased urine phenylethylamine after methylphenidate treatment in children with ADHD. Ann Neurol. 2002 Sep;52(3):372-4.12205654O'Reilly RL, Davis BA: Phenylethylamine and schizophrenia. Prog Neuropsychopharmacol Biol Psychiatry. 1994 Jan;18(1):63-75.7906896Potkin SG, Wyatt RJ, Karoum F: Phenylethylamine (PEA) and phenylacetic acid (PAA) in the urine of chronic schizophrenic patients and controls. Psychopharmacol Bull. 1980 Jan;16(1):52-4.7360842Ferrero DM, Lemon JK, Fluegge D, Pashkovski SL, Korzan WJ, Datta SR, Spehr M, Fendt M, Liberles SD: Detection and avoidance of a carnivore odor by prey. Proc Natl Acad Sci U S A. 2011 Jul 5;108(27):11235-40. doi: 10.1073/pnas.1103317108. Epub 2011 Jun 20.21690383Primary amine oxidaseP46883AMO_ECOLItynAhttp://ecmdb.ca/proteins/P46883.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 + Oxygen + Phenylethylamine > Hydrogen peroxide + Ammonium + PhenylacetaldehydePhenylethylamine + Oxygen + Water <> Phenylacetaldehyde + Ammonia + Hydrogen peroxideR02613Water + Oxygen + Phenylethylamine > Hydrogen ion + Hydrogen peroxide + Ammonia + PhenylacetaldehydeR02613AMINEPHEN-RXNPhenylethylamine + Water + Oxygen > Phenylacetaldehyde + Ammonia + Hydrogen peroxideLuria-Bertani (LB) mediaShake flask0.43uMtrue0.1137 oCBL21 DE3Stationary phase cultures (overnight culture)1716446Lin, Z., Johnson, L. C., Weissbach, H., Brot, N., Lively, M. O., Lowther, W. T. (2007). "Free methionine-(R)-sulfoxide reductase from Escherichia coli reveals a new GAF domain function." Proc Natl Acad Sci U S A 104:9597-9602.17535911