2.02015-06-08 15:28:30 -06002015-08-05 16:22:05 -0600ECMDB23870M2MDB005520Aromatic amino acidAmino acids that include an aromatic ring(+-)-5-Hydroxytryptophan(S)-5-Hydroxytryptophan5-HTP5-Hydroxy-DL-tryptophan5-Hydroxy-tryptophan5-Hydroxyl-L-tryptophan5-Hydroxytryptophan5-Hydroxytryptophan DL-form5-Hydroxytryptophan L form5-Hydroxytryptophan L-formCincofarmDL-5-HTPDL-5-HydroxytryptophanHydroxytryptophanL-5-HydroxytryptophanLevothymLevotinineOxitriptanOxyfanOxytryptophanPretonineQuietimSerotonylTelesolTripteneC11H12N2O3220.2246220.084792262-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acidDL-5-hydroxytryptophanNC(CC1=CNC2=C1C=C(O)C=C2)C(O)=OInChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)LDCYZAJDBXYCGN-UHFFFAOYSA-Nlogp-1.56logs-1.78solubility3.63e+00 g/llogp-1.4pka_strongest_acidic2.15pka_strongest_basic9.18iupac2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acidaverage_mass220.2246mono_mass220.08479226smilesNC(CC1=CNC2=C1C=C(O)C=C2)C(O)=OformulaC11H12N2O3inchiInChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)inchikeyLDCYZAJDBXYCGN-UHFFFAOYSA-Npolar_surface_area99.34refractivity58.18polarizability22.03rotatable_bond_count3acceptor_count4donor_count4physiological_charge0formal_charge0Cysteine and methionine metabolismec00270Tyrosine metabolismec00350Phenylalanine 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.PW000921ec00360MetabolicPhenylalanine, tyrosine and tryptophan biosynthesisec00400Novobiocin biosynthesisec00401Isoquinoline alkaloid biosynthesisec00950Tropane, piperidine and pyridine alkaloid biosynthesisec00960Lysine biosynthesisLysine is biosynthesized from L-aspartic acid. L-aspartic acid can be incorporated into the cell through various methods: C4 dicarboxylate / orotate:H+ symporter ,
glutamate / aspartate : H+ symporter GltP, dicarboxylate transporter , C4 dicarboxylate / C4 monocarboxylate transporter DauA, glutamate / aspartate ABC transporter
L-aspartic acid is phosphorylated by an ATP-driven Aspartate kinase resulting in ADP and L-aspartyl-4-phosphate. L-aspartyl-4-phosphate is then dehydrogenated through an NADPH driven aspartate semialdehyde dehydrogenase resulting in a release of phosphate, NADP and L-aspartic 4-semialdehyde (involved in methionine biosynthesis).
L-aspartic 4-semialdehyde interacts with a pyruvic acid through a 4-hydroxy-tetrahydrodipicolinate synthase resulting in a release of hydrogen ion, water and
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate. The latter compound is then reduced by an NADPH driven 4-hydroxy-tetrahydrodipicolinate reductase resulting in a release of water, NADP and (S)-2,3,4,5-tetrahydrodipicolinate, This compound interacts with succinyl-CoA and water through a tetrahydrodipicolinate succinylase resulting in a release of coenzyme A and N-Succinyl-2-amino-6-ketopimelate. This compound interacts with L-glutamic acid through a N-succinyldiaminopimelate aminotransferase resulting in oxoglutaric acid, N-succinyl-L,L-2,6-diaminopimelate. The latter compound is then desuccinylated by reacting with water through a N-succinyl-L-diaminopimelate desuccinylase resulting in a succinic acid and L,L-diaminopimelate. This compound is then isomerized through a diaminopimelate epimerase resulting in a meso-diaminopimelate (involved in peptidoglyccan biosynthesis I). This compound is then decarboxylated by a diaminopimelate decarboxylase resulting in a release of carbon dioxide and L-lysine.
L-lysine is then incorporated into lysine degradation pathway. Lysine also regulate its own biosynthesis by repressing dihydrodipicolinate synthase and also repressing lysine-sensitive aspartokinase 3.
A metabolic connection joins synthesis of an amino acid, lysine, to synthesis of cell wall material. Diaminopimelate is a precursor both for lysine and for cell wall components. The synthesis of lysine, methionine and threonine share two reactions at the start of the three pathways, the reactions converting L-aspartate to L-aspartate semialdehyde. The reaction involving aspartate kinase is carried out by three isozymes, one specific for synthesis of each end product amino acid. Each of the three aspartate kinase isozymes is regulated by its corresponding end product amino acid.PW000771ec00300MetabolicMetabolic pathwayseco01100Specdb::CMs13457Specdb::CMs32136Specdb::CMs37554Specdb::NmrOneD1385Specdb::MsMs686Specdb::MsMs687Specdb::MsMs688Specdb::MsMs295651Specdb::MsMs295652Specdb::MsMs295653Specdb::MsMs336712Specdb::MsMs336713Specdb::MsMs336714Specdb::MsMs440119Specdb::MsMs445332Specdb::MsMs445333Specdb::MsMs445334Specdb::MsMs445335Specdb::MsMs451955Specdb::NmrTwoD1329C01021Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-GlutamateR03120