N- anthranilic

The following were administered separately to P. cyclopium [carboxyl- and [ N]-anthranilic acid, phenylalanine with labels at positions 1,2, and 3, and also N-labelled phenylalanine and [methyl- C]methiomne. The results show an intact incorporation of all the atoms of phenylalanine and anthranilic acid into both (49) and (50), with L-phenylalanine preferred over the D-isomer. The iV-methyl group originates from the S-methyl group of methionine. The cyclic dipeptide formed from these two amino-acids is presumably an intermediate on the pathway to the alkaloids. As phenylalanine serves as a precursor for cyclopenol, the origin of the hydroxy-group is by meta-hydroxylation of phenylalanine. Further, m-tyrosine and tyrosine are only unspecific precursors. 

Inspect the paper in ultraviolet light—conveniently in front on a Hanovia ultraviolet strip light—in a dark room. The acids show up as intense blue fluorescent spots. Mark with a pencil the positions of all spots. The position of the two spots arising from solution (C) should be compared with the single spots arising from solutions (A) and (B). It is probable that the solution (B) of pure N-methylan-thranilic acid may also reveal a faint spot corresponding to anthranilic acid still present in minute traces in the methylated acid cf. p. 223). 

Record the Rp values of the two acids under the above conditions the anthranilic and the N-methylanthranilic acid should have Rp values of 0-28 and 0 55 respectively. 

The reaction is applicable to the preparation of amines from amides of aliphatic aromatic, aryl-aliphatic and heterocyclic acids. A further example is given in Section IV,170 in connexion with the preparation of anthranilic acid from phthal-imide. It may be mentioned that for aliphatic monoamides containing more than eight carbon atoms aqueous alkaline hypohalite gives poor yields of the amines. Good results are obtained by treatment of the amide (C > 8) in methanol with sodium methoxide and bromine, followed by hydrolysis of the resulting N-alkyl methyl carbamate ... 

Figure 4.6 The bifunctional enzyme PRA-isomerase (PRAI) IGP-synthase (IGPS) catalyzes two sequential reactions in the biosynthesis of tryptophan. In the first reaction (top half), which is catalyzed by the C-terminal PRAI domain of the enzyme, the substrate N-(5 -phosphoribosyl) anthranilate (PRA) is converted to l-(o-carboxyphenylamino)-l-deoxyribulose 5-phosphate (CdRP) by a rearrangement reaction. The succeeding step (bottom half), a ring closure reaction from CdRP to indole-3-glycerol phosphate (IGP), is catalyzed by the N-terminal IGPS domain.

Priestle, J.P, et al. Three-dimensional structure of the bifunctional enzyme N-(5 -phosphoribosyl) anthranilate isomerase-indole-3-glycerol-phosphate synthase from Escheriehia eoli. Proc. Natl. Aead. 

Septentrionaline, C33H45O9N2, is amorphous, m.p. 131°, [a]J, ° + 32-7° (EtOH). Weidemann states that it contains four methoxyl groups, and on hydrolysis by alkalis yields (1) a crystalline acid, CgHgO N, m.p. 125-6°, which on further treatment with alkali yields anthranilic acid, C,H,02N, and must be a near relative of the latter and (2) a basic amorphous product, C25H390,N, m.p. 89°, [a]p °-f- 29-55° (EtOH), which yields a crystalline hydrochloride. 

A general method for malting Camps precursors has been developed/ Treatment of an anthranilic acid 15 with an acid anhydride or chloride in the usual way results in the corresponding benzoxazinone (16). Subsequent treatment with the dianion of an N-substituted acetamide furnishes P-keto amide 17. The reactions were run with crude 16, yields typically 50-80% overall. The effect of substituents on the reaction has not been extensively investigated. 

Chemical Name N-(2,6-Dichloro-3-methylphenyl)anthranilic acid Common Name -... 

A mixture consisting of 22.7 g potassium o-bromobenzoate, 16.6 g 2,6-dichloro-3-methvlani-line, 12 ml N-ethylmorpholine, 60 ml diethylene glycol dimethyl ether, and 1.0 g anhydrous cupric bromide is heated in a nitrogen atmosphere at 145 C to 155°C for 2 hours. The reaction mixture is diluted with 60 ml diethylene glycol dimethyl ether and acidified with 25 ml concentrated hydrochloric acid. The acidic mixture is diluted with 100 ml of water and the liquid phase decanted from the insoluble oil. The insoluble oil is stirred with methanol and the crystalline N-(2,6-dichloro-3-methylphenyl)anthranilic acid which separates is collected and washed with methanol. The product, after recrystallization from acetone-water mixture melts at 248 C to 250°C. 

Chemical Name 2-(2,3-dimethylphenvl)amino] benzoic acid Common Name N-(2,3-xylvl)anthranilic acid Structural Formula ... 

N-(m-methylmercapto-phenyl)-aniline (MP 59° to 61°C) is prepared by condensing m-methyl-mercapto-aniline (BP 163° to 165°C/16 mm Hg) with the potassium salt of o-chloro-benzoic acid and decarboxylating the resultant N-(m-methylmercapto-phenyl)-anthranilic acid (MP 139° to 141°C) by heating, and then distilling. 

This product was dissolved in 10 ml of chloroform. To this solution were added 10 ml of a 10% aqueous solution of caustic soda and the mixture was warmed at 50°C to effect hydrolysis of the ester group. After completion of the reaction, the organic phase was separated, washed with water and distilled to remove the solvent whereby 2.1 g (yield 4B%) of the end product, i.e., N-(3, 4 -dimethoxycinnamoyl)-anthranilic acid, were obtained. This product had a melting point of 211°C to 213°C. 

CjH N 57 -54-/) see Etodolac ethyl 3-anilinocarbanilate (C15H16N2O2 37711-28-7) see Moracizine ethyl anthranilate... 

Taniuchi H, M Hatanaka, S Kuno, O Hayashi, M Nakazima, N Kurihara (1964) Enzymatic formation of catechol from anthranilic acid. J Biol Ghent 239 2204-2211. 

Acids. Acetic acid n-Caproic acid Benzoic acid Phenylacetic acid Succinic acid Adipic acid Anthranilic acid. 

For the preparation of the 2,5-diketopiperazines 9-57 and 1,4-benzodiazepine-2,5-diones 9-58, respectively, the isocyanide 9-54 was either treated with an aldehyde and an amino acid, or with an aldehyde and an anthranilic acid, to give either 9-55 or 9-56, using the conditions depicted in Scheme 9.11. Further transformations include liberation from the resin with KOtBu forming N-acyloxazolidones and treatment with NaOMe to afford the corresponding esters, which are then cy-clized to the desired products 9-57 and 9-58 under acidic conditions. 

Tripeptides with N-terminal anthranilic acid part were used as starting materials in the solid-phase synthesis carried out on TentaGel resin to prepare 1,4,11,1 l -tetrahydro-2//-pyrazino[2,l-3]quinazoline-3,6-diones with various N-l and N-3 substituents <2003EPP1471066>. Tandem cyclization from [6+0] atom fragments took place in the solid-phase synthesis of 143 from 142. Intermediate 141 was built on bromoacetal resin (Scheme 17) <1998JOC3162>. 

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