Pathway anthranilic

In the latter pathway anthranilic acid and aspartic acid are used to construct peganine. In accord with this it has been shown recently that anthranoylaspartic acid (155) is a fairly specific precursor for peganine (154) in A. vasica N-Acetylanthranilic acid (153) is built into peganine intact, so perhaps the most important precursor for peganine may be (156). 

The kynurenine pathway metabolites are kynurenine, kynurenic acid, xahthurenic acid, 3-hydroxykynurenine, anthranilic acid and quinolinic acid. The more important are kynurenine (Kyn) and 3-hydroxykynurenine (30HKyn) (Fig 1). 

Chauhan A, RK Jain (2000) Degradation of o-nitrobenzoate via anthranilic acid (o-aminobenzoate) hyArthro-acterprotophormiae a plasmid-encoded new pathway. Biochem Biophys Res Commun 267 236-244. 

Figure 1. Schematic outline of various products and associated enzymes from the shikimate and phenolic pathways in plants (and some microorganisms). Enzymes (1) 3-deoxy-2-oxo-D-arabino-heptulosate-7-phosphate synthase (2) 5-dehydroquinate synthase (3) shikimate dehydrogenase (4) shikimate kinase (5) 5-enol-pyruvylshikimate-3-phosphate synthase (6) chorismate synthase (7) chorismate mutase (8) prephenate dehydrogenase (9) tyrosine aminotransferase (10) prephenate dehydratase (11) phenylalanine aminotransferase (12) anthranilate synthase (13) tryptophan synthase (14) phenylalanine ammonia-lyase (15) tyrosine ammonia-lyase and (16) polyphenol oxidase. (From ACS Symposium Series No. 181, 1982) (62).

Figure 23 sketches these four pathways, namely the 5,6-dihydroxy-2(lH)quinolinone pathway, the 7,8-dihy-droxy-2(lH)quinolinone pathway, the anthranilate pathway, and the 8-hydroxycoumarin pathway. 

The metabolites identified [327] for each of these pathways are collected in Table 15 and once again, it should be emphasized that only the last two, catechol/anthranilate and coumarin pathways (named c and d, in Fig. 23) yield denitrogenated products. In summary, the four metabolic pathways identified for quinoline transformation, as shown in Fig. 23, are ... 

The microbial pathways observed for the degradation of indole differ significantly between microorganisms. Four pathways have been reported for indole degradation. In the first pathway, the degradation of indole by Desulfobacterium indolicum was reported [339,340] to occur via isatin and anthranilate (Fig. 25). 

The anthranilate intermediate is believed to be metabolized to denitrogenated products. The list of proposed metabolites is also included in Fig. 25. A consortium of anaerobic and denitrifying bacteria was found to degrade indole via oxindole [341], but further details were not given to ensure if pathway 1 was followed. 

An enzymatic pathway for indole degradation was found in A. niger, inducible by the substrate within a 5-h period during growth. Among the enzymes found, anthranilate hydroxylase, N-formylanthranilate deformylase, 2,3-dihydroxybenzoate decarboxylase, and catechol dioxygenase were isolated, and their activities were demonstrated in a cell-free system [342],... 

Alcaligenes sp. Strain IN3 [326] Susanne Fetzner Selective to indole. Degrade through the anthranilic acid pathway... 

Arthrobacter sp. Ru61a Gram (+) [327,350] Susanne Fetzner Quinaldine 4-OR BDN of 2-MeQN through the anthranilic acid pathway. Activity is about 70 times improved by purification from the crude extract. Enzyme activity for QN is three times higher than for quinaldine (2Me-QN). Enzyme selective to most of heterocyclic N-compounds. Attack at the 4th (para)-position. 

Quinacridones are not the only industrially significant products. The list may be extended to include the derivative mentioned in Section 3.2.1.4, the linear trans-quinacridone quinone. There are two other synthetic pathways besides the hydroquinone method. The older method involves cyclization of the 2,5-bis-(2 -carboxyanilino-)-l, 4-benzoquinone 63 with concentrated sulfuric acid or polyphos-phoric acid at 150 to 200°C. The starting material 63 is obtained through condensation of 1,4-benzoquinone with anthranilic acid ... 

The route of formation of the carbazole nucleus is still far from understood, and has been variously considered to arise from 3-prenylquinolone via a pathway involving shikimic acid (394) and mevalonic acid (MVA) (400) (Scheme 3.1) (1,112,362-366), anthranilic acid (397) and prephenic acid (404) via a pathway involving shikimic acid (394) (Scheme 3.2) (367), and also tryptophan (408) involving the mevalonate (400) pathway (Scheme 3.3) (133). All of these pathways lack experimental proof. However, based on the occurrence of the diverse carbazole alkaloids derived from anthranilic acid (397) in the family Rutaceae, the pathway... 

The biogenetic pathway proposed by Chakraborty for the formation of carbazole (1) and 3-methylcarbazole (2) proceeds through Af-phenylated anthranilic acid (406). This hypothesis is based on aromatic C-methylation of aniline with methionine, and originates from anthranilic acid (397) and prephenic acid (404). Until now, there are no N-phenylated anthranilic acid derivatives known naturally, therefore, this hypothesis is lacking substantial biogenetic evidence. However, the isolation of carbazole (1), 3-methylcarbazole (2), and several derivatives of 3-methylcarbazole... 

Figure 1. Hypothetical mechanism for shuttling of intermediates of the common aromatic pathway between plastidic and cytosolic compartments. Enzymes denoted with an asterisk (DAHP synthase-Co, chorismate mutase-2, and cytosolic anthranilate synthase) have been demonstrated to be isozymes located in the cytosol. DAHP molecules from the cytosol are shown to be shuttled into the plastid compartment in exchange for EPSP molecules synthesized within the plastid. Abbreviations C3, phosphoenolpyruvate C4, erythrose 4-P DAHP, 3-deoxy-D-arabino-heptulosonate 7-phosphate EPSP, 5-enolpyruvylshikimate 3-phosphate CHA, chorismate ANT, anthranilate TRP, L-tryptophan PPA, prephenate AGN, L-arogenate TYR, L-tyrosine and PHE, L-phenylalanine.

Alkaloids derived from L-tryptophan hold the indole nucleus in a ring system. The ring system originates in the shikimate secondary compounds building block and the anthranilic acid pathway. It is known that the shikimate block. 

An alternative method for the production of methyl anthranilate with the help of Bacillus megaterium was recently reported by Taupp et al. [78] the latter pathway resulted in higher yields of methyl anthranilate. 

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