2.0 2012-05-31 14:29:50 -0600 2015-10-02 02:25:51 -0600 ECMDB20144 M2MDB000992 D-Phenylalanine D-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 acid D-&alpha;-amino-&beta;-phenylpropionate D-&alpha;-amino-&beta;-phenylpropionic acid D-a-amino-b-Phenylpropionate D-a-amino-b-Phenylpropionic acid D-alpha-Amino-beta-phenylpropionate D-alpha-Amino-beta-phenylpropionic acid D-b-Phenyl-a-alanine D-b-Phenylalanine D-beta-Phenyl-alpha-alanine D-beta-Phenylalanine D-α-amino-β-Phenylpropionate D-α-amino-β-Phenylpropionic acid D-β-Phenyl-α-alanine D-β-Phenylalanine DL-phnylalanine DPN P1751_SIGMA Phenyl-D-Alanine Phenylalanine Phenylalanine D-form Sabiden C9H11NO2 165.1891 165.078978601 (2S)-2-amino-3-phenylpropanoic acid L-phenylalanine 673-06-3 NC(CC1=CC=CC=C1)C(O)=O InChI=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-N Cytoplasm Periplasm logp -1.35 ALOGPS logs -1.60 ALOGPS solubility 4.14e+00 g/l ALOGPS logp -1.2 ChemAxon pka_strongest_acidic 2.47 ChemAxon pka_strongest_basic 9.45 ChemAxon iupac (2S)-2-amino-3-phenylpropanoic acid ChemAxon average_mass 165.1891 ChemAxon mono_mass 165.078978601 ChemAxon smiles NC(CC1=CC=CC=C1)C(O)=O ChemAxon formula C9H11NO2 ChemAxon inchi InChI=1S/C9H11NO2/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8H,6,10H2,(H,11,12) ChemAxon inchikey COLNVLDHVKWLRT-UHFFFAOYSA-N ChemAxon polar_surface_area 63.32 ChemAxon refractivity 45.12 ChemAxon polarizability 17.03 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Phenylalanine metabolism The 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. PW000921 ec00360 Metabolic inner membrane transport list 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 added PW000786 Metabolic Specdb::CMs 389 Specdb::CMs 390 Specdb::CMs 391 Specdb::CMs 1252 Specdb::CMs 1304 Specdb::CMs 2830 Specdb::CMs 30069 Specdb::CMs 30210 Specdb::CMs 30607 Specdb::CMs 30732 Specdb::CMs 30771 Specdb::CMs 31032 Specdb::CMs 31033 Specdb::CMs 37329 Specdb::CMs 138002 Specdb::CMs 145736 Specdb::CMs 1051754 Specdb::CMs 1051755 Specdb::CMs 1051757 Specdb::EiMs 1975 Specdb::NmrOneD 1118 Specdb::NmrOneD 1177 Specdb::NmrOneD 142590 Specdb::NmrOneD 142591 Specdb::NmrOneD 142592 Specdb::NmrOneD 142593 Specdb::NmrOneD 142594 Specdb::NmrOneD 142595 Specdb::NmrOneD 142596 Specdb::NmrOneD 142597 Specdb::NmrOneD 142598 Specdb::NmrOneD 142599 Specdb::NmrOneD 142600 Specdb::NmrOneD 142601 Specdb::NmrOneD 142602 Specdb::NmrOneD 142603 Specdb::NmrOneD 142604 Specdb::NmrOneD 142605 Specdb::NmrOneD 142606 Specdb::NmrOneD 142607 Specdb::NmrOneD 142608 Specdb::NmrOneD 142609 Specdb::NmrOneD 166451 Specdb::MsMs 248 Specdb::MsMs 249 Specdb::MsMs 250 Specdb::MsMs 3191 Specdb::MsMs 3192 Specdb::MsMs 3193 Specdb::MsMs 3194 Specdb::MsMs 3195 Specdb::MsMs 3196 Specdb::MsMs 3197 Specdb::MsMs 3198 Specdb::MsMs 3199 Specdb::MsMs 3200 Specdb::MsMs 3201 Specdb::MsMs 3202 Specdb::MsMs 3203 Specdb::MsMs 3204 Specdb::MsMs 3205 Specdb::MsMs 3206 Specdb::MsMs 3207 Specdb::MsMs 3208 Specdb::MsMs 3209 Specdb::MsMs 3210 Specdb::MsMs 3211 Specdb::MsMs 3212 Specdb::NmrTwoD 975 Specdb::NmrTwoD 1177 71567 969 C02265 16998 CPD-216 Keseler, 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. 21097882 Kanehisa, 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. 22080510 Winder, 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. 18331064 D-amino acid dehydrogenase small subunit P0A6J5 DADA_ECOLI dadA http://ecmdb.ca/proteins/P0A6J5.xml Uncharacterized amino-acid ABC transporter ATP-binding protein yecC P37774 YECC_ECOLI yecC http://ecmdb.ca/proteins/P37774.xml Inner membrane amino-acid ABC transporter permease protein yecS P0AFT2 YECS_ECOLI yecS http://ecmdb.ca/proteins/P0AFT2.xml Aromatic amino acid transport protein AroP P15993 AROP_ECOLI aroP http://ecmdb.ca/proteins/P15993.xml Phenylalanine-specific permease P24207 PHEP_ECOLI pheP http://ecmdb.ca/proteins/P24207.xml D-Phenylalanine + Water + Acceptor <> Phenylpyruvic acid + Ammonia + Reduced acceptor R01374 Phenylpyruvic acid + Ammonia + cytochrome c nitrite reductase <> D-Phenylalanine + Water + cytochrome c nitrite reductase PW_R003457