Indole pyruvic acid

Gronowitz adapted this technology to one-pot syntheses of indole-3-acetic acids and indole-3-pyruvic acid oxime ethers from A-BOC protected o-iodoanilines [328, 329]. Rawal employed the Pd-catalyzed cyclization of A-(o-bromoallyl)anilines to afford 4- and 6-hydroxyindoles, and a 4,6-dihydroxyindole [330], and Yang and co-workers have used a similar cyclization to prepare 8-carbolines 287 and 288 as illustrated by the two examples shown [331]. The apparent extraneous methyl group in 288 is derived from triethylamine. 

Another example of a partially biomimetic strategy is shown in Fig. 25b. Here the analogy is to the starting materials two indole-containing molecules, 136 and 137, which were dimerized via formation of the same bond as seen in the reaction carried out by StaD on two molecules of indole-3-pyruvic acid imine (125). This bond - between the (3-carbons of the L-tryptophan precursor (123) - once formed biosynthetically leads to 127, which spontaneously forms chromopyrrolic acid (128) in oxygen (Fig. 24). In the biosynthetic route, this reaction is between two unactivated carbons, which would seem to render it challenging, although low levels of 128 formation are seen between indole-3-acetic acid, L-tryptophan, and... 

Overall, the biosynthesis of 160 is characterized by the dimerization of 168 to give the central structure of the molecule. This head-to-tail dimerization strategy is efficient, using the same substrate twice, and is a sensible route, given the existence of the shikimate pathway, which provides, in turn, a precursor to 168. An analogous dimerization route can be seen for the biosynthesis of K252c (1), described in Sect. 5, where two molecules of indole-3-pyruvic acid imine (125), derived in turn from L-tryptophan (123), are dimerized to give an intermediate that leads to chromopyrrolic acid (128). In both cases, the monomer precursors, either 168 or 125, serve as both nucleophiles and electrophiles, and are activated to react by the presence of the appropriate enzymes. 

When the extraction is done with acetone, no methyl abscisate is recovered. Acetone has also been used for recovery of natural IAA esters (18, 32). Another approach to minimize formation of methyl esters has been to extract with hot water (53). Dichloro-methane has been used (71) in preference to methanol or ethanol to minimize the conversion of indole-3-pyruvic acid to IAA. 

C11H9N03 indole-3-pyruvic acid 392-12-1 25.00 1.2743 2 21710 C11H11N 3,4-dimethyl quinoline 2436-92-2 20.86 1.0491 2... 

One of the most efficient enzymatic systems that generates triplet state acetone is the horse radish peroxidase(HRP)-catalyzed oxygenation of isobutyraldehyde (Eq. 79). Related enzymatic processes include the autoxidation of linear carbox-aldehydes, malonaldehyde, a-formylphenylacetic acid, indole-3-acetal-dehyde, indole-3-pyruvic acid, ° and indole-3-acetaldehyde. Consequently, there is no question about the existence of enzymatically generated electronic excitation in the cell however, what do these excited states do in the biological system ... 

Tryptophan synthase (EC 4.1.2.20) normally catalyzes the synthesis of tryptophan from serine by the oc,p elimination-addition reaction outlined in Scheme 5 where X = OH and Z = indole. The B protein of the oligomeric enzyme will catalyze the dehydration of serine, and in the presence of PLP and mercaptoethanol, the intermediate 15 will form adduct 25. This will then react as in Scheme 9 to yield the ketoacid 26 and pyridoxamine-phosphate 6. The net transamination has been shown to involve protonation at the 4 -Si face in yielding PMP (30). When the apoenzyme of tryptophan synthase is reconstituted with the unnatural substrates (4 / )- or (4 S)-[4- H,]pyridox-amine-phosphate and indole-3-pyruvic acid, an unnatural transamination... 

K. Takahashi, H. Yokomizo, K. Ishiyama, M. Kitsuta, M. Ohashi, New aspects of cyclodextrin chemistry induced by outside type complex formation asymmetric reduction of indol-3-pyruvic acid with NaBH4, J. Incl. Phenom. Macrocyc. Chem., 2006, 56, 95-99. 

The cyclization of o-halo A-allylaniline has been applied to the preparation of cycloprop[c]indol-5-ones, indole-3-acetic acids and hetero analogs, indole-3-pyruvic acid oxime ether, 5-(sulfamoylmethyl)indoles, the anti-migrsLinc agent CP-122,288, and the protected A-unit of CC-1065. In addition, the cyelization of -vinylaniline has been applied to 6>-vinyl-A-tosylanilines, o-vinylacetanilides, and vinyl-A-... 

Figure 5.42 Proposed tryptophan-dependent indole acetic acid biosynthesis pathways for Arabidopsis. Dashed arrows indicate that neither a gene nor enzyme activity has been identified in Arabidopsis. lAM, indole-3-acetamide IPA, indole-3-pyruvic acid lAAld, indole-3-acetaldehyde lAOx, indole-3-acetaldoxime 5-lAH-L-cys,...

The chemical structure of heteroauxin was established to be indole-3-acetic acid (indole-P-acetic acid (lAA)). It is considered that lAA is formed by the enzymatic oxidation of indole-3-acetaldehyde derived from tryptophan via indole-3-pyruvic acid or tryptamine. Between these two routes, the main route is thought to be through indole-3-pyruvic acid. 

Indoleacetic acid (lAA) (17) is involved in many aspects of plant growth and development (Bonner and Varner, 1976 Kosuge and Sanger, 1986). This hormonal substance is derived in most plants by conversion of tryptophan to indole 3-pyruvic acid (15) (tryptophan amino transferase), decarboxylation to the indole 3-acetaldehyde (16) (indole pyruvate decarboxylase), and oxidation to indole 3-acetic acid (17) (indole acetaldehyde oxidase) (Fig. 7.6) (Goodwin and Mercer, 1983). 

Caution is demanded when ammoniacal or acid solvents are used in investigations on plant auxin metabolism. Indole-3-pyruvic acid and glucobrassicin decompose during TLC in ammonia-containing media. Good separation of a number of indole derivatives is possible in solvents... 

Indole-3-pyruvic acid 8464 Isohexane 7552 Isopropyl salicylate 6501... 

Tryptophan is metabolized by several different pathways (Fig. 1) each yielding biologically important substances such as tryptamine and in particular serotonin (5-hydroxytryptamine), which seems to be involved in certain mental disorders. Indole-3-acetic acid is a plant growth hormone its precursor is tryptamine or indole-3-pyruvic acid. In humans, the microorganisms of the large intestine can further degrade indole-3-acetic acid to yield indole, skatole (3-methyl-indole) and other substances. 

---