Microbial metabolism of pyridinium compounds. Metabolism of 4-carboxy-1-methylpyridinium chloride, a photolytic product of paraquat

Abstract

1. A bacterium, Achromobacter D, isolated from garden soil by elective culture, utilized N-methylisonicotinic acid (4-carboxy-1-methylpyridinium chloride) as sole carbon source. 2. Extracts of N-methylisonicotinate-grown cells oxidized this substrate only after supplementation with a source of nicotinamide nucleotides and then consumed 1 mol of O(2) and released 1 mol of CO(2)/mol of N-methylisonicotinate supplied. 3. The N-methyl group of the substrate was released as methylamine whereas the five C atoms of the pyridine ring were accounted for as succinate and formate. The CO(2) evolved by extracts was believed to derive from the carboxyl group on C-4 of the heterocyclic ring. 4. The immediate precursor of the succinate end-product was succinic semialdehyde; the inducible nature of succinic semialdehyde dehydrogenase in N-methylisonicotinate-grown cells supported this finding. 5. There was no evidence for monohydroxylation of the ring, but the time sequence of the appearance of the end-products indicated that the oxygen-requiring, NADH-requiring and decarboxylation steps clearly preceded the formation of methylamine and succinate. 6. The results are consistent with the oxidative cleavage of a partially reduced heterocyclic ring followed by several hydrolytic and dehydrogenase steps resulting in the appearance of the end-products.

Methyl‐Hydroxypyridinecarboxylic Acids as Possible Bidentate Chelating Agents for Aluminium(III): Synthesis and Metal–Ligand Solution Chemistry

“…[9] Next, the hydroxyacids were N-methylated by use of a conventional method (CH 3 I in dimethylformamide). [11] Solution Equilibria…”

Microbial degradation of pyridine by Paracoccus sp. isolated from contaminated soil

“…Since 1910s, researchers have isolated some microbial organisms degrading pyridine and its derivatives including hydroxypyridine, alkylpyridine and carboxypyridine, and elucidated microbial metabolic pathway of these compounds [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16]. There were some examples as following.…”

“…There were some examples as following. A group leaded by Cain [1,2,5,[9][10][11][12] from U.K. obtained some pure cultures with the ability to utilize pyridine as sole source of carbon, nitrogen and energy, and its hydroxy derivatives as principal carbon source by elective culture either from sewage of an activated-sludge plant or a few crumbs of soil. Five pure strains were selected for detailed study.…”

A new pathway for isonicotinate degradation by Mycobacterium sp. INA1

“…Reductive steps are not very common in the aerobic metabolism of heteroaromatics, and the compounds involved are generally not activated. This was shown for the degradation of isonicotinate by Bacillus brevis (Singh & Shukla, 1986), of N-methylisonicotinate by Achrornobacter D (Wright & Cain, 1972), and of pyridine by a Corynebacteriurn sp. (Shukla & Kaul, 1974).…”