Indole-3-carboxylic acid, tryptophan

Hopkins and Cole had obtained by the oxidation of tryptophane with ferric chloride a body of the composition of C9H7NO this body has been shown by Ellinger to be /8-indole-aldehyde, firstly by oxidising it to /8-indole-carboxylic acid,... 

In addition to the reagents for detection which are quoted in Table 88, many others have been mentioned in the literature [89, 90, 104] for urine metabolites [78] for serotonine metabolites [14] for hydroxyindoles and -tryptophans [35] with comprehensive data for hydroxyskatoles [19] for the methyl esters of indole-carboxylic acids [i2, 23, 63] for glucobrassicin. 2,4-Dinitrophenylhydrazine (Rgt. No. 82) is suitable for the often feebly reactive indole-aldehydes. 

Various intermediate products derived from tryptophane have been reported as occasional urinary constituents. These include indole aldehyde, indole acetic acid, scatoxyl, and indole carboxylic acid. Indole and scatole, themselves, are improbable urinary constituents. 

C iH FjNO, J254S3-3I-0) see Dolasetron mesilate indole-3-carboxylic acid imidazolide (CiiHoNjO 99445-26-S) see Tropisetron (S)-indoline-2-carboxylic acid (QjH.jNOj 79815-20-6) see Perindopril ( )-2-(lH-indol-5-yl)-A -methylethenesulfonamide (CiiHijNjOjS 98623-49-5) see Naratriptan 5-(3-indolylmcthyl)hydantoin (Ci2H N,02 21753-16-2) see L-Tryptophan... 

Combination of MCR with the Pictet-Spengler cyclization also leads to different types of scaffolds with ketopiperazine fused ring systems. Tetrahydro-jS-carboline scaffold 221 was prepared in a convergent, two-step procedure [67]. An array of indole derivatives was prepared by the reaction of tryptophan derivative 222, aldehyde 223, carboxylic acid 224, and bifunctional amine 214 (Scheme 40). 

Indole-3-acetaldoxime (30) and 4-hydroxyphenylacetaldoxime were shown to be metabolized by plant and pest fungi to 32 and to other related indole- and 4-hydroxyphenyl carboxylic acids, however, the biochemical transformation differed between the two fungi. These biochemical transformations may be relevant to the ability of certain fungi to cause plant diseases . Compound 30 has been shown to be a key intermediate in the biosynthesis of camalexin, 3-thiazolyl-2 -yl-indole, a member of the family of phytoalexins that are produced in response to pathogen attack. It was demonstrated that CYP71A13 catalyzes the conversion of 30 to indole-3-acetonitrile, which is essential for the biosynthesis of camalexin. Thus, the literature supplies a large body of evidence for the existence of a set of enzymes dedicated to the production of the auxin, 32, from tryptophan via indole-3-acetaldoxime (30). 

In 1990, Nakamura et al. reported for the first time the complete biosynthetic origin of the whole carbon skeleton of carbazomycin B isolated from lower plants (378). Based on feeding experiments with and C-labeled compounds, followed by measurement of radioactivity and C-NMR spectroscopy, it was shown that L-tryptophan (408) contributes to C-3 and C-4 of the hexasubstituted aromatic ring, in addition to the indole ring, indicating tryptophan as the progenitor of carbazomycin B (261), in contrast to Chakraborty s proposal of 2-methylcarbazole. The indole part of L-tryptophan (408) is formed by incorporation of two carbons from phosphor-ibosyl diphosphate (430), with loss of the anthraniiic acid (397) carboxyl. The... 

Contrary to carbon enterosorbents, Enterosgel does not possess an ability for selective removal of albumin-bound ligands regardless of their affinity with the protein carrier - weak (L-tryptophane), medium (sodium caprylate, deoxycholic acid), or strong (indole-3-carboxylic acid and unconjugated bilirubin). It means that if protein-bound toxins are removed by Enterosgel, this occurs simultaneously with adsorption of the carrier protein. 

Haitnup Disease 1 4a. Type I (kidney 4- gut) ( 4b. Type II (kidney) f (recessive) Neutral monoamino, mono-carboxylic acids (except imino adds, methionine and ar nine) Neutral amino adds (atmormal urinary indole pattern due to bacteria] tamv on of tryptophan) Mental retardation and psychosis, episodic cerebellar ataxia, pellagraUke sjmaptoins and abnormal plantar reflex (nicotinamide therapy) Chromatography shows increase of urinary monoamino, mono-carboxyHc adds (B2, B20, E5. E12. H17, H18, H19, J5. M8. M8, P12, R9.T3a... 

We shall adopt this convention and therefore exclude the last-mentioned groups of acids from this review and shall furthermore exclude other nitrogen-containing acids, such as pyrrolidone-carboxylic acid, indoles, and other metabolites of tryptophan (e.g., anthranilic, hydroxyan-thranilic, kynurenic, xanthurenic, and nicotinic acids), imidazolic metabolites or histidine (e.g., fl-imidazolylpyruvic and urocanic acids), acidic guanidine derivatives, and carbamylated acids, as well as acidic com-... 

Amino Acids and Peptides. - Wasserman s method of one-carbon homologation of carboxylic acids to give a-ketocarboxylates involves reaction with cyanomethylenetriphenyl-phosphorane followed by ozone (Scheme 24) and has been used as a key step in a chemo-enzymatic synthesis of isotopically labelled L-valine, L-isoleucine, and o/fo-isoleucine. Alkylation of the carbanion derived from the imino-substituted methylphosphonate diphenyl ester (186) with indol-3-ylmethyl bromide followed by appropriate deprotection has been used to prepare the phosphonate analogue (187) of tryptophan (Scheme 25). The deprotected analogue (188) and derived peptides show activity as inhibitors of chymotrypsin. Two approaches to solid phase Wadsworth-Enunons reactions which have applications in combinatorial chemistry have been reported. In one diethylphosphonoacetamide is bound to PEG-PAL resin via a peptide link, while... 

The Pictet-Spengler reaction has been combined with Ugi multi-component chemistry to construct a number of polycyclic indoles. Isonitrile derivatives prepared from tryptamine (or methyl tryptophanate), a carboxylic acid and formaldehyde condense with aminoacetaldehyde diethyl acetal. A few examples employed substituted aldehydes [352]. 

Even more convoluted are the structures of the indolic spiroindimicins, e.g., A (49) and D (50) from a deep-sea-derived Streptomyces sp. though the two tryptophan residues (one colored red (gray in print versions)) can be clearly discerned (2012OL3364). A tryptophan unit is also visible in the structure of cottoquinazoline D (51), isolated from a coral-associated fungus Aspergillus versicolor (20110L1130). This structure also includes a 1-aminocyclopropane-l-carboxylic acid residue. 

Indole-3-acetonitrile Indole-3-aldehyde Indole-3-carboxylic acid Indole-3-acetic acid Indole-3-methanol Skatole Tryptophan... 

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