Microbial desulfonation of substituted naphthalenesulfonic acids and benzenesulfonic acids

Sulfur-limited batch enrichment cultures containing one of nine multisubstituted naphthalenesulfonates and an inoculum from sewage yielded several taxa of bacteria which could quantitatively utilize 19 sulfonated aromatic compounds as the sole sulfur source for growth. Growth yields were about 4 kg of protein per mol of sulfur. Specific degradation rates were about 4 to 14 mu kat/kg of protein. A Pseudomonas sp., an Arthrobacter sp., and an unidentified bacterium were examined. Each desulfonated at least 16 aromatic compounds, none of which served as a carbon source. Pseudomonas sp. strain S-313 converted 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, benzenesulfonic acid, and 3-aminobenzenesulfonic acid to 1-naphthol, 2-naphthol, 5-amino-1-naphthol, phenol, and 3-aminophenol, respectively. Experiments with 18O2 showed that the hydroxyl group was derived from molecular oxygen.     

Microbial desulfonation of substituted naphthalenesulfonic acids and benzenesulfonic acids.

Sulfur-limited batch enrichment cultures containing one of nine multisubstituted naphthalenesulfonates and an inoculum from sewage yielded several taxa of bacteria which could quantitatively utilize 19 sulfonated aromatic compounds as the sole sulfur source for growth. Growth yields were about 4 kg of protein per mol of sulfur. Specific degradation rates were about 4 to 14 mu kat/kg of protein. A Pseudomonas sp., an Arthrobacter sp., and an unidentified bacterium were examined. Each desulfonated at least 16 aromatic compounds, none of which served as a carbon source. Pseudomonas sp. strain S-313 converted 1-naphthalenesulfonic acid, 2-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, benzenesulfonic acid, and 3-aminobenzenesulfonic acid to 1-naphthol, 2-naphthol, 5-amino-1-naphthol, phenol, and 3-aminophenol, respectively. Experiments with 18O2 showed that the hydroxyl group was derived from molecular oxygen.     

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 × hollandica cv. Wedgwood, Roseda lutea L. and Reseda 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 trans-aminations, and that (3-carboxyphenyl)glycine and (3-carboxy-4-hydroxy-phenyl)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 cinnamics acids are not metabolized at all in the plants.     

Anticonvulsant activity of benzylamides of some amino acids and heterocyclic acids

A series of new potential anticonvulsants have been synthesized. They are N-methyl benzyl-amides of N-methyl Asp and N-methyl Glu (R and S), benzylamides of some heterocyclic acids and their N-oxides and benzylamides of two heteroalicyclic acids. The obtained compounds were evaluated in the Anticonvulsant Screening Project (ASP) of Antiepileptic Drug Development Program (ADDP) of NIH.     

The determination of aldonic acids and 2-C-methylaldonic acids

Specific, spectrophotometric methods are described for the determination of glyoxylic acid from aldonic acids and pyruvic acid from 2-C-methylaldonic acids, which allow their determination in admixture. Confirmation of the classification of these aldonic acids is obtained by ion-exchange chromatography of the products of periodate oxidation.     

Correlation between medium C-chain fatty acids and polyunsaturated fatty acids

The medium C-chain fatty acids increased in the muscle, lungs, pancreas and adipose tissue (and not in the liver) of the rats injected with CCl4 or nourished with "balanced" diet for the lipids. When CCl4 and balanced diet are furnished together, these acids decrease strongly: the discussion of the results is difficult.     

Gustatory responses of eel palatine receptors to amino acids and carboxylic acids

The gustatory receptors of the eel palate were found to be extremely sensitive to amino acids and carboxylic acids. The results obtained are as follows: (a) 11 amino acids which are among naturally occurring amino acids elicited responses in the palatine nerve, but 9 amino acids did not elicit a response even at a high concentration. The effect of D-amino acids was always much less than that of their corresponding L-isomers. There was no appreciable difference in the effectiveness of an alpha-amino acid (alpha-alanine) and beta-amino acid (beta-alanine). (b) The threshold concentrations of the most potent amino acids (arginine, glycine) were between 10(-8) and 10(-9) M. A linear relation between the magnitude of the response and log stimulus concentration held for a wide concentration range for all the amino acids examined. (c) The palatine receptors responded sensitively to various carboxylic acid solutions whose pH was adjusted to neutral. The threshold concentrations varied between 10(-4) and 10(-7) M. The magnitude of the response at 10(-2) M increased with an increase of carbon chain length. (d) The extent of cross-adaptation was examined with various combinations of amino acids. A variety of the response patterns showing complete cross-adaptation, no cross-adaptation, or synergetic interaction was observed. The synergetic interaction was also observed when one amino acid below its threshold concentration was added to the other amino acid below its threshold concentration was added to the other amino acid. No cross-adaptation was observed between amino acids and fatty acids. (e) The treatment of the palate with papain led to loss of the responses to arginine, glycine, and histidine without affecting those to proline and acetic acid. The treatment with pronase E eliminated selectively the response to proline. The possibility that the eel gustatory receptors are responsible for sensing food at a distance was discussed.     

The reactions of the sulfur-containing amino acids with phosphoric and sulfuric acids

Both cystine and cysteine react very differently toward 6.0 M phosphoric and sulfuric acids. With phosphoric acid, extensive decomposi tion occurs; with sulfuric acid, very little.Cystine, in phosphoric acid at 100 °C. produces hydrogen sulfide, free sulfur, cysteic acid, ammonia, alanine, serine, and pyruvic acid. Cysteine produces a similar series but with marked quantitative differences.Cystine, in sulfuric acid, is merely racemized.Methionine is largely demethylated by sulfuric acid under these conditions. It is practically inert toward phosphoric acid.The behavior of hair toward phosphoric and sulfuric acids is similar to that of cystine but is modified by reactions of other hydrolytic products.     

The phenyl - and -L-idopyranosiduronic acids and some other aryl glycopyranosiduronic acids

Condensation of 1,2,3,4,6-penta-O-acetyl-á-l-idopyranose (1) with phenol yielded phenyl 2,3,4,6-tetra-O-acetyl-α- (2) and α-l-idopyranoside (4). Deacetylation of 2 and 4 afforded phenyl α and β-l-idopyranosides (3 and 5), respectively, the structures of which were verified by periodate oxidation studies. A platinum-catalyzed oxidation of 3 and 5 produced the amorphous phenyl α- and β-L-idopyranosiduronic acids (9 and 11), respectively, which were isolated as the crystalline cyclohexylammonium salts. Phenyl β- and α-d-glucopyranosiduronic acids are apparent minor byproducts of the catalytic oxidations, resulting from an inversion at C-5. _p-Nitrophenyl α-d-mannopyranosiduronic acid and _p-nitrophenyl α- and β-d-galactopyranosiduronic acids are also described.