2.02012-08-09 09:25:03 -06002015-06-03 17:21:34 -0600ECMDB21467M2MDB0018621-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate1-(2-carboxyphenylamino)-1'-deoxyribulose-5'-phosphate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. It is an intermediate in the synthesis of tryptophan from chorismate.1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphoric acidC12H13NO9P346.2067346.0327925312-{[3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoate2-{[3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoateOC(COP([O-])([O-])=O)C(O)C(=O)CNC1=CC=CC=C1C([O-])=OInChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/p-3QKMBYNRMPRKVTO-UHFFFAOYSA-KCytoplasmlogp-0.09logs-1.42solubility1.51e+01 g/llogp-0.5pka_strongest_acidic1.48pka_strongest_basic0.27iupac2-{[3,4-dihydroxy-2-oxo-5-(phosphonatooxy)pentyl]amino}benzoateaverage_mass346.2067mono_mass346.032792531smilesOC(COP([O-])([O-])=O)C(O)C(=O)CNC1=CC=CC=C1C([O-])=OformulaC12H13NO9PinchiInChI=1S/C12H16NO9P/c14-9(11(16)10(15)6-22-23(19,20)21)5-13-8-4-2-1-3-7(8)12(17)18/h1-4,10-11,13,15-16H,5-6H2,(H,17,18)(H2,19,20,21)/p-3inchikeyQKMBYNRMPRKVTO-UHFFFAOYSA-Kpolar_surface_area182.11refractivity86.31polarizability29.58rotatable_bond_count9acceptor_count9donor_count3physiological_charge-3formal_charge-3tryptophan metabolism IIThe biosynthesis of L-tryptophan begins with L-glutamine interacting with a chorismate through a anthranilate synthase which results in a L-glutamic acid, a pyruvic acid, a hydrogen ion and a 2-aminobenzoic acid. The aminobenzoic acid interacts with a phosphoribosyl pyrophosphate through an anthranilate synthase component II resulting in a pyrophosphate and a N-(5-phosphoribosyl)-anthranilate. The latter compound is then metabolized by an indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in a 1-(o-carboxyphenylamino)-1-deoxyribulose 5'-phosphate. This compound then interacts with a hydrogen ion through a indole-3-glycerol phosphate synthase / phosphoribosylanthranilate isomerase resulting in the release of carbon dioxide, a water molecule and a (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate. The latter compound then interacts with a D-glyceraldehyde 3-phosphate and an Indole. The indole interacts with an L-serine through a tryptophan synthase, β subunit dimer resulting in a water molecule and an L-tryptophan.
The metabolism of L-tryptophan starts with L-tryptophan being dehydrogenated by a tryptophanase / L-cysteine desulfhydrase resulting in the release of a hydrogen ion, an Indole and a 2-aminoacrylic acid. The latter compound is isomerized into a 2-iminopropanoate. This compound then interacts with a water molecule and a hydrogen ion spontaneously resulting in the release of an Ammonium and a pyruvic acid. The pyruvic acid then interacts with a coenzyme A through a NAD driven pyruvate dehydrogenase complex resulting in the release of a NADH, a carbon dioxide and an Acetyl-CoAPW001916MetabolicSpecdb::MsMs23345Specdb::MsMs23346Specdb::MsMs23347Specdb::MsMs30143Specdb::MsMs30144Specdb::MsMs3014524784954van 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 370:17-25.17765195Tryptophan biosynthesis protein trpCFP00909TRPC_ECOLItrpChttp://ecmdb.ca/proteins/P00909.xml N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphatePW_R0053551-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphate + Hydrogen ion > Carbon dioxide + Water + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphate + (1S,2R)-1-C-(indol-3-yl)glycerol 3-phosphatePW_R005357