Microbial Metabolism of Quinoline and Related Compounds. XVII. Degradation of 3-Methylquinoline by Comamonas testosteroni 63

Schach, Susanne; Schwarz, Gerhild; Fetzner, Susanne; Lingens, Franz

doi:10.1515/bchm3.1993.374.1-6.175

Cited by 22 publications

(6 citation statements)

References 20 publications

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“…Whereas pyridine itself is attacked via a reductive step (Watson & Cain, 1975), the bacterial catabolism of many substituted pyridine derivatives was found to involve hydroxylations of the heteroaromatic ring (for review, see Shukla, 1984). This is also true for quinoline (benzopyridine) (Grant & Al-Najjar, 1976), isoquinoline (Aislabie et al, 1989) and some quinoline derivatives (Bauer & Lingens, 1992;Schach et al, 1993). Due to the electron distribution, the pyridine ring permits nucleophilic attack in the orthoand para-positions (Sims & O'Loughlin, 1989).…”

Section: Introductionmentioning

confidence: 97%

Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase

Kretzer

Frunzke

Andreesen

1993

Journal of General Microbiology

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Catabolism of isonicotinate by Mycobucterium sp. INAl has been shown to proceed via 2-hydroxyisonicotinate, 2,6-dihydroxyisonicotinate (citrazinate), citrazyl-CoA and 2,6-dioxopiperidine-4-carboxyl-CoA. An extended pathway involving propane-1,2,3-tricarboxylate as a further intermediate is presented in this paper. Propane-1,2,3-tricarboxylate was oxidized stepwise to 2-oxoglutarate involving an oxidase, aconitase and isocitrate dehydrogenase. Isonicotinate dehydrogenase catalyses the first step of isonicotinate metabolism in Mycobacterium sp. INA1. The enzyme was purified to apparent homogeneity by a three-step procedure. Enrichment was accompanied by partial loss in specific activity. The native enzyme had a molecular mass of either 125 kDa or 250 kDa, when estimated by native gradient PAGE or gel filtration, respectively. SDS-gel electrophoresis revealed three types of subunits with molecular masses of approximately 83, 31 and 19 kDa. N-Terminal amino acid sequences of all three subunits have been determined. Molybdenum, iron, acid-labile sulphur and FAD were present at molar ratios of 1, 4, 4, 1 per protomer (125 kDa). The molybdenum-complexing cofactor was shown to be molybdopterin cytosine dinucleotide. Besides isonicotinate, only quinoline-4carboxylate was found to be oxidized at appreciable rates.

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Section: Introductionmentioning

confidence: 97%

Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase

Kretzer

Frunzke

Andreesen

1993

Journal of General Microbiology

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“…This explains the discrepancy between the experimentally observed transformation and the thermodynamic estimate for several reactions (r0337, r0502, r0765, r0782, and r0815). In the case of three reactions (r0051, r0872, and r1104), the product has been hypothesized but not explicitly identified (Fournier et al, 2002; Schach et al, 1993; van Herwijnen et al, 2003). In our examination of the literature, we were unable to identify the reason for the inconsistency between experimental observations and thermodynamic estimates for the remaining five reactions.…”

Section: Resultsmentioning

confidence: 99%

Thermodynamic analysis of biodegradation pathways

Finley

Broadbelt

Hatzimanikatis

2009

Biotech & Bioengineering

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Microorganisms provide a wealth of biodegradative potential in the reduction and elimination of xenobiotic compounds in the environment. One useful metric to evaluate potential biodegradation pathways is thermodynamic feasibility. However, experimental data for the thermodynamic properties of xenobiotics is scarce. The present work uses a group contribution method to study the thermodynamic properties of the University of Minnesota Biocatalysis/Biodegradation Database. The Gibbs free energies of formation and reaction are estimated for 914 compounds (81%) and 902 reactions (75%), respectively, in the database. The reactions are classified based on the minimum and maximum Gibbs free energy values, which accounts for uncertainty in the free energy estimates and a feasible concentration range relevant to biodegradation. Using the free energy estimates, the cumulative free energy change of 89 biodegradation pathways (51%) in the database could be estimated. A comparison of the likelihood of the biotransformation rules in the Pathway Prediction System and their thermodynamic feasibility was then carried out. This analysis revealed that when evaluating the feasibility of biodegradation pathways, it is important to consider the thermodynamic topology of the reactions in the context of the complete pathway. Group contribution is shown to be a viable tool for estimating, a priori, the thermodynamic feasibility and the relative likelihood of alternative biodegradation reactions. This work offers a useful tool to a broad range of researchers interested in estimating the feasibility of the reactions in existing or novel biodegradation pathways.

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“…[24] 5,6-Dihydroxy-1H-2-oxoquinoline (18) presumably also is an intermediate in the degradation of quinoline (10) by Comamonas testosteroni 63, [25] Pseudomonas putida K1, [26] Rhodococcus sp. B1, [21] a Moraxella sp., [27] and perhaps a Nocardia sp.…”

Section: 6-dihydroxy-1h-2-oxoquinoline Pathwaymentioning

confidence: 99%

“…[23] b) 5,6-Dihydroxy-1H-2-oxoquinoline pathway: degradation of quinoline (10) and 3-methylquinoline (11) by Comamonas testosteroni 63. [24] c) 7,8-Dihydroxy-1H-2-oxoquinoline pathway: degradation of 4-methylquinoline by Pseudomonas putida K1. [26] d) 8-Hydroxycoumarin pathway: degradation of quinoline (10) by Pseudomonas putida 86, [21] Pseudomonas fluorescens 3, [21] Pseudomonas stutzeri, and Pseudomonas pseudoalcaligenes.…”

Section: Reviewsmentioning

confidence: 99%

Bacterial Degradation of Quinoline and Derivatives—Pathways and Their Biocatalysts

Fetzner

Tshisuaka

Lingens

et al. 1998

Angewandte Chemie International Edition

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A series of interesting enzymes were discovered during investigations on the degradation of quinoline by microorganisms. These include the molybdenum-containing hydroxylases that catalyze the transformation 1→2 and the unusual 2,4-dioxygenases that catalyze the reaction 3→4. The application of the hydroxylases may even be interesting in industry, because several quinoline derivatives are used as pharmaceuticals or agrochemicals.

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Microbial Metabolism of Quinoline and Related Compounds. XVII. Degradation of 3-Methylquinoline by Comamonas testosteroni 63

Cited by 22 publications

References 20 publications

Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase

Catabolism of isonicotinate by Mycobacterium sp. INA1: extended description of the pathway and purification of the molybdoenzyme isonicotinate dehydrogenase

Thermodynamic analysis of biodegradation pathways

Bacterial Degradation of Quinoline and Derivatives—Pathways and Their Biocatalysts

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