Formylanthranilic acid

Alkyl- and aryl-substituted carboxylic acid derivatives such as ethyl 4-methoxybenzoate, diethyl phthalate,104 aryl- and alkylcarboxylic add halides or anhydrides10,2 5 8 give benzoxazinones (193). When IA was brominated in glacial acetic acid, 193 (R2 = CHBr2) was obtained.259 Anthranilic acid (4) with A-methyl IA (24) leads to 194, which cyclizes in sulfuric acid to the benzoxazinone 195134 (Scheme 33). Reaction of /V-formylanthranilic acid (196) (available from 1A and formic acid) with IA again yields the quina-zolinone 19710 260 (Eq. 19). 

Amino-2-hydroxy[4- C]butyric acid (the corresponding aldehyde has been condensed with o-aminobenzaldehyde to give vasicine 4-hydroxy-[2- C]glutamic acid (found with vasicine in Linaria yw/garis ), N-methyl-anthranilic acid, and N-formylanthranilic acid have been tested as vasicine precursors in A. vasica, without success. 

Kynurenine Formylase. Hydrolysis of formylkynurenine to kynurenine is catalyzed in liver preparations by an enzyme (formylase or kynurenine formamidase) with rather low specificity for aromatic formamides. The reaction with formylkynurenine, however, is faster than that with any analogs. A very similar enzyme has been obtained from Neurospora. In contrast, an enzyme from insects does not hydrolyze formylanthranilic acid, a model substrate for formylase from other sources, or other analo-... 

An unidentified rod-shaped gram-negative organism isolated from tap water has been adapted to indole (634). Analysis of simultaneous adaptations indicates that in this organism indole is oxidized by the following steps indole - (indoxyl) - (dihydroi indole) - isatin - formylanthranilic acid - anthranilic acid - salicylic acid... 

An insufficient amount of information is available for classification of this enzyme, but, if formylanthranilic acid is directly formed by the consumption of one molecule of oi gen per molecule of indole, the reaction bears strong resemblance to the enzymic oxidation of tryptophan. However, the consumption of oiQrgen per molecule substrate, and the nature of the reaction product remain to be determined. 

Irradiation of both soluble and fibrous proteins with ultraviolet light leads to considerable destruction of cystine and aromatic acid residues, in particular tryptophan. However, apart from a small degree of conversion to formylkynurenine and/or kynurenine residues, all attempts to ascertain the nature of the tryptophan photoproducts have so far been unsuccessful (72, 63, 303, 304). Pirie and Dilley 304) have proposed that photo-oxidation of tryptophan to formylkynurenine is followed by splitting out of N-formylanthranilic acid (60). Rivett s... 

Steam distillation of the glycidic acid (98)178,183 proceeds with elimination of water and carbon dioxide to give 3-formylanthranil (anthroxanaldehyde, 99).183... 

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