Iron(II)-dependent dioxygenase and N-formylamide deformylase catalyze the reactions from 5-hydroxy-2-pyridone to maleamate

Yao, Yuxiang; Tang, Hongzhi; Ren, Huixue; Yu, Hao; Wang, Limin; Zhang, Wei; Behrman, E. J.; Xu, Ping

doi:10.1038/srep03235

Cited by 14 publications

(27 citation statements)

References 35 publications

(72 reference statements)

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“…adductive product of 6-hydroxy picolinic acid (6-HPA). In general, the first step for biodegradation of 2-PA is introduced a hydroxyl group on α carbon adjacent to N atom so that 6-HPA is generated [1,2]. In this paper, the experimental findings were consistent with these literatures [1,2].…”

Section: Initial Phsupporting

confidence: 88%

“…Pyridine-contained wastewater mainly stems from mining, coal and shale oil industry processing, wood preservative treatment, medicine and food industry, dye manufacture and agricultural production, etc. [1,2]. Due to its high toxicity and carcinogenicity, pyridines are listed as priority-controlled pollutants by United States Environmental Protection Agency [2].…”

Section: Introductionmentioning

confidence: 99%

“…[1,2]. Due to its high toxicity and carcinogenicity, pyridines are listed as priority-controlled pollutants by United States Environmental Protection Agency [2]. 2-Picolinic acid, a kind of pyridine compounds, is intensively used for the manufacture of pharmacy, pesticides, daily chemical products, and additives of animal husbandry foods [3,4].…”

Section: Introductionmentioning

confidence: 99%

“…However, quantitatively describing the degradation process of 2-PA by microbes are still absent. Moreover, it is also unknown that whether 2-PA can be utilized by other species of microorganism or not [1,2]. In this paper, a strain was able to use 2-PA as a sole source of carbon, nitrogen and energy under aerobic conditions was isolated.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Aerobic Biodegradation of 2-Picolinic Acid by a Comamonas sp.

Wang¹,

Zheng²,

Yurui³

et al. 2017

J Environ Anal Toxicol

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Section: Initial Phsupporting

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Aerobic Biodegradation of 2-Picolinic Acid by a Comamonas sp.

Wang¹,

Zheng²,

Yurui³

et al. 2017

J Environ Anal Toxicol

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“…VppE is a 2,5-DHP dioxygenase that transformed 2,5-DHP to N-formylmaleamic acid. 2,5-DHP is a central metabolic intermediate in the catabolism of many pyridine derivatives (23,30). Genome sequencing promotes the study of molecular mechanisms of xenobiotic degradation (13,22), because genes can be identified through sequence alignment with isoenzymes or enzymes with similar functions.…”

Section: Discussionmentioning

confidence: 99%

Molecular Mechanism of Nicotine Degradation by a Newly Isolated Strain, Ochrobactrum sp. Strain SJY1

Tang

Zhu

et al. 2015

Appl Environ Microbiol

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A newly isolated strain, SJY1, identified as Ochrobactrum sp., utilizes nicotine as a sole source of carbon, nitrogen, and energy. Strain SJY1 could efficiently degrade nicotine via a variant of the pyridine and pyrrolidine pathways (the VPP pathway), which highlights bacterial metabolic diversity in relation to nicotine degradation. A 97-kbp DNA fragment containing six nicotine degradation-related genes was obtained by gap closing from the genome sequence of strain SJY1. Three genes, designated vppB, vppD, and vppE, in the VPP pathway were cloned and heterologously expressed, and the related proteins were characterized. The vppB gene encodes a flavin-containing amine oxidase converting 6-hydroxynicotine to 6-hydroxy-N-methylmyosmine. Although VppB specifically catalyzes the dehydrogenation of 6-hydroxynicotine rather than nicotine, it shares higher amino acid sequence identity with nicotine oxidase (38%) from the pyrrolidine pathway than with its isoenzyme (6-hydroxy-L-nicotine oxidase, 24%) from the pyridine pathway. The vppD gene encodes an NADH-dependent flavin-containing monooxygenase, which catalyzes the hydroxylation of 6-hydroxy-3-succinoylpyridine to 2,5-dihydroxypyridine. VppD shows 62% amino acid sequence identity with the hydroxylase (HspB) from Pseudomonas putida strain S16, whereas the specific activity of VppD is ϳ10-fold higher than that of HspB. VppE is responsible for the transformation of 2,5-dihydroxypyridine. Sequence alignment and phylogenetic analysis suggested that the VPP pathway, which evolved independently from nicotinic acid degradation, might have a closer relationship with the pyrrolidine pathway. The proteins and functional pathway identified here provide a sound basis for future studies aimed at a better understanding of molecular principles of nicotine degradation. N icotine, which easily passes biological membranes, is significantly harmful to humans and is considered a potentially addictive drug (1, 2). Large quantities of tobacco waste with high concentrations of nicotine are generated annually by cigarette and cigar manufacturing (3). Due to its water solubility, nicotine can easily spread in the environment, emerging as a threat to public health (3). As a result, the U.S. Environmental Protection Agency classified nicotine as a "toxic release inventory" chemical in 1994 (4). Microbes play significant roles in removing nicotine from the environment, and in the meantime, they serve as the catalysts for biotransformation. Nicotine could potentially be used for the production of value-added chemicals. 6-Hydroxy-3-succinoylpyridine (HSP), an important precursor for the synthesis of compounds with biological activities, was efficiently produced by an engineered nicotine-degrading strain (5). Therefore, the study of the mechanism of nicotine degradation provides useful information for both bioremediation and biocatalysis.Many microorganisms that use various nicotine degradation pathways have been isolated from the environment, including Arthrobacter (6), Pseudomonas (7, 8), Ochroba...

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Genome-wide investigation of the genes involved in nicotine metabolism in Pseudomonas putida J5 by Tn5 transposon mutagenesis

Xia

Zhang

Lei

et al. 2015

Appl Microbiol Biotechnol

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Pseudomonas putida J5 is an efficient nicotine-degrading bacterial strain isolated from the tobacco rhizosphere. We successfully performed a comprehensive whole-genome analysis of nicotine metabolism-associated genes by Tn5 transposon mutagenesis in P. putida J5. A total of 18 mutants with unique insertions screened from 16,324 Tn5-transformants failed to use nicotine as the sole carbon source. Flanking sequences of the Tn5 transposon were cloned with a shotgun method from all of the nicotine-growth-deficient mutants. The potentially essential products of mutated gene were classified as follows: oxidoreductases, protein and metal transport systems, proteases and peptidases, transcriptional and translational regulators, and unknown proteins. Bioinformatic analysis of the Tn5 insertion sites indicated that the nicotine metabolic genes were separated and widely distributed in the genome. One of the mutants, M2022, was a Tn5 insert into a gene encoding a homolog of 6-hydroxy-L-nicotine oxidase, the second enzyme of nicotine metabolism in Arthrobacter nicotinovorans. Genetic and biochemical analysis confirmed that three open reading frames (ORFs) from an approximately 13-kb fragment recovered from the mutant M2022 were responsible for the transformation of nicotine to 3-succinoyl-pyridine via pseudooxynicotine and 3-succinoyl semialdehyde-pyridine, the first three steps of nicotine degradation. Further research on these mutants and the Tn5-inserted genes will help us characterize nicotine metabolic processes in P. putida J5.

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Iron(II)-dependent dioxygenase and N-formylamide deformylase catalyze the reactions from 5-hydroxy-2-pyridone to maleamate

Cited by 14 publications

References 35 publications

Aerobic Biodegradation of 2-Picolinic Acid by a Comamonas sp.

Aerobic Biodegradation of 2-Picolinic Acid by a Comamonas sp.

Molecular Mechanism of Nicotine Degradation by a Newly Isolated Strain, Ochrobactrum sp. Strain SJY1

Genome-wide investigation of the genes involved in nicotine metabolism in Pseudomonas putida J5 by Tn5 transposon mutagenesis

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