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At least 19 recordsLinked to original sources

Intermediates in the metabolism of m-carboxy-substituted aromatic amino acids in plants. Phenylpyruvic acids, mandelic acids, and phenylglyoxylic acids.

Tracer experiments with 14C-labelled precursors in Iris times hollandica cv. Wedgwood, Reseda Iutea L. And Keseda Odorata L. have demonstrated that 3-(3-carboxyphenyl) alanine and 3-(3-carboxy-4-hydroxyphenyl) alanine can be derived from the corresponding pyruvic acids, presumably by unspecific transaminations, and that (3-carboxyphenyl) glycine and (3-carboxy-4-hydroxyphenyl) glycine can be derived from the corresponding phenylglyoxylic acids. The glycine derivatives are derived from the alanine derivatives, and the corresponding mandelic acids are intermediates in these transformations. The corresponding phenylacetic acids are incorporated only slightly into the glycine derivatives, indicating that oxidation at the benzylic position in the C6-C3 compounds takes place early in the transformation. The corresponding cinamic acids are not metabolized at all in the plants.

Alcohols↗

[The simultaneous determination of hippuric acid, o-, m-, p-methylhippuric acids, mandelic acid and phenylglyoxylic acid in urine by HPLC].

A high-performance liquid chromatographic method is described for the simultaneous determination of six metabolites of aromatic hydrocarbons: hippuric acid (HA) from toluene; o-, m-, p-methylhippuric acids (o-, m-, p-MHA) from xylene; mandelic acid (MA) and phenylglyoxylic acid (PGA) from styrene and ethylbenzene. Metabolites were first extracted from urine by solid phase extraction with anion exchange resin, then isocratically separated on a C8 column with 3 microns particle size, 10 cm length and 3 mm internal diameter. Mobile phase was prepared diluting 16 mL of tetrahydrofuran, 14 mL of acetronitrile and 5 mL of methanol to 500 mL with phosphoric acid/potassium dihydrogen phosphate buffer 0.01 M (pH 2.7). The internal standard was 3-hydroxybenzoic acid. Chromatographic runs were completed in about 21 min. The accuracy and reproducibility obtained make this method useful for the biological monitoring of occupational exposure to toluene, xylene, styrene and ethylbenzene.

Chromatography, High Pressure Liquid↗

Isotachophoretic analysis of mandelic acid, phenylglyoxylic acid, hippuric acid and methylhippuric acid in urine after occupational exposure to styrene, toluene and/or xylene.

A simple, rapid and sensitive analytical method has been developed for the determination of phenylglyoxylic acid, mandelic acid, hippuric acid and methylhippuric acid; 0-, m- and p-methylhippuric acids are partly separated. These compounds are found as metabolites after occupational exposure to styrene, toluene and xylene. The method has been applied successfully to samples extracted from human urine by diethyl ether. The method can be used to accurately and simultaneously determine as little as 0.5 nmole of all of these acids in less than 20 min.

Chromatography, Gas↗

Reaction pathways of in vivo stereoselective conversion of ethylbenzene to (-)-mandelic acid.

1. Mandelic acid formed in vivo from ethylbenzene as well as from various oxidation intermediates was laevo mandelic acid and was of surprisingly high optical purity. 2. Reaction sequences are proposed for the stepwise oxidation of ethylbenzene to mandelic acid. 3. Although the initial hydroxylation of ethylbenzene to methylphenyl-carbinol is stereoselective, the optical activity of mandelic acid is not established at this point since the optical centre is destroyed in the second step, dehydrogenation to acetopheneone. 4. Acetophenone appears to be a precursor of not only mandelic acid and benzoylformic acid but benzoic acid as well. 5. The route from acetophenone involves conversion to omega-hydroxyacetophenone and subsequent reduction to glycol and/or oxidation to phenylglyoxal. 6. The configuration of mandelic acid is determined either during reduction of hydroxyacetophenone or reduction of phenylglyoxal.

Animals↗

[Determination of the urinary metabolites hydroxyindole-acetic acid, vanillyl mandelic acid and homovanillic acid by means of lipophilic gel chromatography and gas chromatography (author's transl)].

A specific and practicable method is described for the quantitative determination of urinary phenol- and indole-carboxylic acids. High specificity is achieved by a preliminary separation of the free acids (extracted from the urine sample) with the aid of organophilic gel chromatography on Sephadex LH 20, followed by gas chromatographic analysis of the silyl derivatives of the acids. The organophilic gel chromatography of the free acids shows a high recovery rate in the micro- and submicrogram range. The difficulties encountered in other techniques in the derivatisation and gas chromatographic separation of the individual components are avoided by using the preliminary separation, and by using N-methyl-N-trimethylsilyl-trifluoroacetamide for the derivatisation. Use of this preparation technique with a direct read-out gas chromatograph with automatic sample introduction, gives high accuracy and precision, and a facility for the determination of a wide range of aromatic acids in urine.

Chromatography, Gas↗

Involvement of 4-hydroxymandelic acid in the degradation of mandelic acid by Pseudomonas convexa.

A microorganism capable of degrading DL-mandelic acid was isolated from sewage sediment of enrichment culture and was identified as Pseudomonas convexa. It was found to metabolize mandelic acid by a new pathway involving 4-hydroxymandelic acid, 4-hydroxybenzaldehyde, 4-hydroxybenzoic acid, and 3,4-dihydroxybenzoic acid as aromatic intermediates. All the enzymes of the pathway were demonstrated in cell-free extracts. L-Mandelate-4-hydroxylase, a soluble enzyme, requires tetrahydropteridine, nicotinamide adenine dinucleotide phosphate, reduced form, and Fe2+ for its activity. The next enzyme, L-4-hydroxymandelate oxidase (decarboxylating), a particulate enzyme, requires flavine adenine dinucleotide and Mn2+ for its activity. A nicotinamide adenine dinucleotide-dependent, as well as a nicotinamide adenine dinucleotide phosphate-dependent, benzaldehyde dehydrogenase has been resolved and partially purified.

Carboxy-Lyases↗