2.02012-05-31 14:29:50 -06002015-10-02 02:25:51 -0600ECMDB20144M2MDB000992D-PhenylalanineD-phenylalanine is a member of the chemical class known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Phenylalanine (abbreviated as Phe or F) is an alpha-amino acid with the formula C6H5CH2CH(NH2)COOH. This essential amino acid is classified as nonpolar because of the hydrophobic nature of the benzyl side chain. Metabolic engineering can enhance phenylalanine production in E. coli[PMID: 18080813] D-phenylalanine can be synthesized by glucose fermentation in E. coli using metabolic engineering. DAHP synthase and chorismate mutase-prephenate dehydratase form a pathway where L-phenylalanine synthesis is deregulated and L-phenylalanine is converted into D-phenylalanine [Applied Biocatalysis in Specialty Chemicals and Pharmaceuticals, Chapter 5, p 65-75, Chapter DOI: 10.1021/bk-2001-0776.ch005](2R)-2-amino-3-phenylpropanoate(2R)-2-amino-3-phenylpropanoic acid(R)-2-Amino-3-phenylpropionate(R)-2-Amino-3-phenylpropionic acidD-α-amino-β-phenylpropionateD-α-amino-β-phenylpropionic acidD-a-amino-b-PhenylpropionateD-a-amino-b-Phenylpropionic acidD-alpha-Amino-beta-phenylpropionateD-alpha-Amino-beta-phenylpropionic acidD-b-Phenyl-a-alanineD-b-PhenylalanineD-beta-Phenyl-alpha-alanineD-beta-PhenylalanineD-α-amino-β-PhenylpropionateD-α-amino-β-Phenylpropionic acidD-β-Phenyl-α-alanineD-β-PhenylalanineDL-phnylalanineDPNP1751_SIGMAPhenyl-D-AlaninePhenylalaninePhenylalanine D-formSabidenC9H11NO2165.1891165.078978601(2S)-2-amino-3-phenylpropanoic acidL-phenylalanine673-06-3NC(CC1=CC=CC=C1)C(O)=OInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)COLNVLDHVKWLRT-UHFFFAOYSA-NCytoplasmPeriplasmlogp-1.35logs-1.60solubility4.14e+00 g/llogp-1.2pka_strongest_acidic2.47pka_strongest_basic9.45iupac(2S)-2-amino-3-phenylpropanoic acidaverage_mass165.1891mono_mass165.078978601smilesNC(CC1=CC=CC=C1)C(O)=OformulaC9H11NO2inchiInChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12)inchikeyCOLNVLDHVKWLRT-UHFFFAOYSA-Npolar_surface_area63.32refractivity45.12polarizability17.03rotatable_bond_count3acceptor_count3donor_count2physiological_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.PW000921ec00360Metabolicinner membrane transportlist of inner membrane transport complexes, transporting compounds from the periplasmic space to the cytosol
This pathway should be updated regularly with the new inner membrae transports addedPW000786MetabolicSpecdb::CMs389Specdb::CMs390Specdb::CMs391Specdb::CMs1252Specdb::CMs1304Specdb::CMs2830Specdb::CMs30069Specdb::CMs30210Specdb::CMs30607Specdb::CMs30732Specdb::CMs30771Specdb::CMs31032Specdb::CMs31033Specdb::CMs37329Specdb::CMs138002Specdb::CMs145736Specdb::CMs1051754Specdb::CMs1051755Specdb::CMs1051757Specdb::EiMs1975Specdb::NmrOneD1118Specdb::NmrOneD1177Specdb::NmrOneD142590Specdb::NmrOneD142591Specdb::NmrOneD142592Specdb::NmrOneD142593Specdb::NmrOneD142594Specdb::NmrOneD142595Specdb::NmrOneD142596Specdb::NmrOneD142597Specdb::NmrOneD142598Specdb::NmrOneD142599Specdb::NmrOneD142600Specdb::NmrOneD142601Specdb::NmrOneD142602Specdb::NmrOneD142603Specdb::NmrOneD142604Specdb::NmrOneD142605Specdb::NmrOneD142606Specdb::NmrOneD142607Specdb::NmrOneD142608Specdb::NmrOneD142609Specdb::NmrOneD166451Specdb::MsMs248Specdb::MsMs249Specdb::MsMs250Specdb::MsMs3191Specdb::MsMs3192Specdb::MsMs3193Specdb::MsMs3194Specdb::MsMs3195Specdb::MsMs3196Specdb::MsMs3197Specdb::MsMs3198Specdb::MsMs3199Specdb::MsMs3200Specdb::MsMs3201Specdb::MsMs3202Specdb::MsMs3203Specdb::MsMs3204Specdb::MsMs3205Specdb::MsMs3206Specdb::MsMs3207Specdb::MsMs3208Specdb::MsMs3209Specdb::MsMs3210Specdb::MsMs3211Specdb::MsMs3212Specdb::NmrTwoD975Specdb::NmrTwoD117771567969C0226516998CPD-216Keseler, 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 80:2939-2948.18331064D-amino acid dehydrogenase small subunitP0A6J5DADA_ECOLIdadAhttp://ecmdb.ca/proteins/P0A6J5.xmlUncharacterized amino-acid ABC transporter ATP-binding protein yecCP37774YECC_ECOLIyecChttp://ecmdb.ca/proteins/P37774.xmlInner membrane amino-acid ABC transporter permease protein yecSP0AFT2YECS_ECOLIyecShttp://ecmdb.ca/proteins/P0AFT2.xmlAromatic amino acid transport protein AroPP15993AROP_ECOLIaroPhttp://ecmdb.ca/proteins/P15993.xmlPhenylalanine-specific permeaseP24207PHEP_ECOLIphePhttp://ecmdb.ca/proteins/P24207.xmlD-Phenylalanine + Water + Acceptor <> Phenylpyruvic acid + Ammonia + Reduced acceptorR01374Phenylpyruvic acid + Ammonia + cytochrome c nitrite reductase <> D-Phenylalanine + Water + cytochrome c nitrite reductasePW_R003457