Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions.

Kaiser, Jean‐Pierre; Feng, Yanfang; Bollag, Jean‐Marc

doi:10.1128/mmbr.60.3.483-498.1996

Cited by 185 publications

(135 citation statements)

References 60 publications

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“…In the present study, strain M43 displayed a relatively narrow substrate range among many pyridine derivatives as is the case with many microorganisms degrading alkylpyridines (Kaiser et al, 1996). Interestingly, although 2-hydroxy-4-methylpyridine, the putative intermediate of 4-MP degradation, was easily used as a growth substrate, none of the hydroxylated pyridines were degraded.…”

Section: Degradation Of Pyridine and Related Compoundsmentioning

confidence: 54%

“…Biodegradation of alkylpyridines could be initiated by one of the three following reactions: (i) reduction of the aromatic ring, (ii) oxidation of the alkyl group and (iii) oxidation of the aromatic ring (Sims & O'Loughlin, 1989). Although the key intermediates have not been found, numerous reports suggest initial reduction of the pyridine ring during the degradation of pyridine (Shukla & Kaul, 1974;Watson & Cain, 1975;Rhee et al, 1997) and alkylpyridines (Shukla, 1974;Lee et al, 2001, for reviews, see Kaiser et al, 1996;Fetzner, 1998). In contrast, oxidation of alkyl groups in alkylpyridines was reported only with a 3-methylpyridine (3-MP)-degrading Pseudomonas sp.…”

Section: Introductionmentioning

confidence: 99%

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Aerobic biodegradation of 4-methylpyridine and 4-ethylpyridine by newly isolatedPseudonocardiasp. strain M43

Lee

Yoon

Yang

et al. 2006

FEMS Microbiology Letters

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A filamentous bacterium capable of utilizing 4-methylpyridine and 4-ethylpyridine as the sole source of carbon, nitrogen and energy was isolated from sludge. The organism, designated as strain M43, clustered most closely with members of the genus Pseudonocardia by 16S rRNA gene sequence analysis. During the degradation of 4-methylpyridine and 4-ethylpyridine, c. 60% of nitrogen in the pyridine ring was released as ammonia. Metabolite analyses showed that 2-hydroxy-4-methylpyridine and 2-hydroxy-4-ethylpyridine were transiently accumulated during the degradation of 4-methylpyridine and 4-ethylpyridine, respectively. Strain M43 was also able to degrade pyridine, 3,4-dimethylpyridine, 4-carboxypyridine and 2-hydroxy-4-methylpyridine. The results indicate that degradation of 4-methylpyridine and 4-ethylpyridine by strain M43 proceeded via initial hydroxylation.

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Section: Degradation Of Pyridine and Related Compoundsmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Aerobic biodegradation of 4-methylpyridine and 4-ethylpyridine by newly isolatedPseudonocardiasp. strain M43

Lee

Yoon

Yang

et al. 2006

FEMS Microbiology Letters

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“…NicD and NicF are homologous to Nfo and Ami respectively. Moreover, 2-picolinic acid, pyridine-2-carboxamide, 2-hydroxy-pyridine and Nmethylisonicotinic acid are degraded through similar microbial metabolic pathways (Kaiser et al, 1996). Furthermore, during the uric acid catabolism pathway in Bacillus, the purine ring is cleaved to produce allantoin, which has two amide bonds.…”

Section: Discussionmentioning

confidence: 99%

“…CO-NH) bonds ( Fig. S1A; Kaiser et al, 1996). The amide bonds generated may occur in the middle or at the terminal ends of the N-heterocyclic degradation products, resulting in the presence of either a formaldehyde or an amino group at the end of the molecule.…”

Section: Introductionmentioning

confidence: 99%

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Structural insights into the specific recognition of N‐heterocycle biodenitrogenation‐derived substrates by microbial amide hydrolases

Chen

Tang

et al. 2014

Molecular Microbiology

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SummaryN-heterocyclic compounds from industrial wastes, including nicotine, are environmental pollutants or toxicants responsible for a variety of health problems. Microbial biodegradation is an attractive strategy for the removal of N-heterocyclic pollutants, during which carbon-nitrogen bonds in N-heterocycles are converted to amide bonds and subsequently severed by amide hydrolases. Previous studies have failed to clarify the molecular mechanism through which amide hydrolases selectively recognize diverse amide substrates and complete the biodenitrogenation process. In this study, structural, computational and enzymatic analyses showed how the N-formylmaleamate deformylase Nfo and the maleamate amidase Ami, two pivotal amide hydrolases in the nicotine catabolic pathway of Pseudomonas putida S16, specifically recognize their respective substrates. In addition, comparison of the α-β-α groups of amidases, which include Ami, pinpointed several subgroupcharacteristic residues differentiating the two classes of amide substrates as containing either carboxylate groups or aromatic rings. Furthermore, this study reveals the molecular mechanism through which the specially tailored active sites of deformylases and amidases selectively recognize their unique substrates. Our work thus provides a thorough elucidation of the molecular mechanism through which amide hydrolases accomplish substrate-specific recognition in the microbial N-heterocycles biodenitrogenation pathway.

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Sex, age, and family differences in the chemical composition of owl monkey (Aotus nancymaae) subcaudal scent secretions

MacDonald

Fernández-Duque

Evans³

et al. 2007

American J Primatol

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Numerous behavioral studies have shown that animals use olfactory cues as inbreeding avoidance or kin avoidance mechanisms, implying that scent is unique to families. However, few studies have analyzed the chemical profile of a scent and ascertained the messages that are conveyed in scent secretions. Owl monkeys (Aotus nancymaae) are socially monogamous primates that utilize scent when interacting with foreign conspecifics. This suggests there is a difference in the chemical composition of scent marks. We chemically analyzed sub-caudal gland samples from three families of captive owl monkeys (Aotus nancymaae). Samples were analyzed by capillary GC-MS and relative retention time and fragment pattern was compared with known standards. Gland samples were high in large plant-based shikikate metabolites and fatty ketones; alcohols, acids, and acetates were virtually absent. Gender, age, and family could be reliably classified using discriminant analysis (92.9, 100, and 100%, respectively). Female scent profiles were greater in concentration of aromatic plant metabolites, possibly the result of a different diet or physiological differences in female metabolism as compared to male. Offspring of adult age still living in their natal group showed a less complex chemical profile than their parents. Finally, each family had its own unique and complex chemical profile. The presence of family scent may play a role in mediating social interactions.

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Microbial metabolism of pyridine, quinoline, acridine, and their derivatives under aerobic and anaerobic conditions.

Cited by 185 publications

References 60 publications

Aerobic biodegradation of 4-methylpyridine and 4-ethylpyridine by newly isolatedPseudonocardiasp. strain M43

Aerobic biodegradation of 4-methylpyridine and 4-ethylpyridine by newly isolatedPseudonocardiasp. strain M43

Structural insights into the specific recognition of N‐heterocycle biodenitrogenation‐derived substrates by microbial amide hydrolases

Sex, age, and family differences in the chemical composition of owl monkey (Aotus nancymaae) subcaudal scent secretions

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