2.02015-09-08 17:50:02 -06002015-09-14 16:46:10 -0600ECMDB24200M2MDB006317 N-(5-phosphoribosyl)-anthranilateN-(5-Phosphoribosyl)-anthranilate is a member of the chemical class known as Pentoses. These are monosaccharides in which the carbohydrate moiety contains five carbon atoms. N-(5-phosphoribosyl)-anthranilate is invovled in tryptophan biosynthesis. N-(5'-Phosphoribosyl)anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escherichia coli is a monomeric bifunctional enzyme of Mr 49,500 that catalyzes two sequential reactions in the biosynthesis of tryptophan. (PMID 3303031) Phosphoribosyl anthranilate isomerase from Thermotoga maritima is an extremely stable and active homodimer. (PMID 8897600) N-(5-Phosphoribosyl)-anthranilic acidC12H13NO9P346.209346.034438742-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoate2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoateOC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=OInChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3PMFMJXPRNJUYMB-UHFFFAOYSA-Klogp0.09logs-1.27solubility2.15e+01 g/llogp-0.15pka_strongest_acidic1.23pka_strongest_basic-2.1iupac2-({3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}amino)benzoateaverage_mass346.209mono_mass346.03443874smilesOC1C(O)C(NC2=C(C=CC=C2)C([O-])=O)OC1COP([O-])([O-])=OformulaC12H13NO9PinchiInChI=1S/C12H16NO9P/c14-9-8(5-21-23(18,19)20)22-11(10(9)15)13-7-4-2-1-3-6(7)12(16)17/h1-4,8-11,13-15H,5H2,(H,16,17)(H2,18,19,20)/p-3inchikeyPMFMJXPRNJUYMB-UHFFFAOYSA-Kpolar_surface_area174.27refractivity84.67polarizability29.01rotatable_bond_count6acceptor_count9donor_count3physiological_charge-3formal_charge-3Tryptophan metabolismThe 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-CoA
PW000815ec00380Metabolictryptophan 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::NmrOneD329142Specdb::NmrOneD329143Specdb::NmrOneD329144Specdb::NmrOneD329145Specdb::NmrOneD329146Specdb::NmrOneD329147Specdb::NmrOneD329148Specdb::NmrOneD329149Specdb::NmrOneD329150Specdb::NmrOneD329151Specdb::NmrOneD329152Specdb::NmrOneD329153Specdb::NmrOneD329154Specdb::NmrOneD329155Specdb::NmrOneD329156Specdb::NmrOneD329157Specdb::NmrOneD329158Specdb::NmrOneD329159Specdb::NmrOneD329160Specdb::NmrOneD329161Specdb::MsMs23768Specdb::MsMs23769Specdb::MsMs23770Specdb::MsMs30566Specdb::MsMs30567Specdb::MsMs30568Anthranilate synthase component IIP00904TRPG_ECOLItrpDhttp://ecmdb.ca/proteins/P00904.xmlTryptophan biosynthesis protein trpCFP00909TRPC_ECOLItrpChttp://ecmdb.ca/proteins/P00909.xml2-Aminobenzoic acid + Phosphoribosyl pyrophosphate > Pyrophosphate + N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilatePW_R002895 N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphate + 1-(o-carboxyphenylamino)-1'-deoxyribulose 5'-phosphatePW_R002896 N-(5-phosphoribosyl)-anthranilate + N-(5-phosphoribosyl)-anthranilate > 1-(2-Carboxyphenylamino)-1'-deoxyribulose-5'-phosphatePW_R005355