ArticleThe Journal of biological chemistry2010
Coenzyme A-dependent aerobic metabolism of benzoate via epoxide formation.
Article in The Journal of biological chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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Who cites it
25 citing papers in PubMed, 53 citations in OpenAlex.
- Metagenomic analyses of a consortium for the bioremediation of hydrocarbons polluted soils.AMB Express · 2024Article
- Enzymatic reactions towards aldehydes: An overview.Flavour and fragrance journal · 2023Review
- Unveiling lignocellulolytic trait of a goat omasum inhabitant Klebsiella variicola strain HSTU-AAM51 in light of biochemical and genome analyses.Brazilian journal of microbiology : [publication of the Brazilian Society for Microbiology] · 2022Article
- Progress in structural and functional study of the bacterial phenylacetic acid catabolic pathway, its role in pathogenicity and antibiotic resistance.Frontiers in microbiology · 2022Review
- Novel clades of soil biphenyl degraders revealed by integrating isotope probing, multi-omics, and single-cell analyses.The ISME journal · 2021Article
- An Aerobic Hybrid Phthalate Degradation Pathway via Phthaloyl-Coenzyme A in Denitrifying Bacteria.Applied and environmental microbiology · 2020Article
- Genomic and proteomic analysis of lignin degrading and polyhydroxyalkanoate accumulating β-proteobacteriumBiotechnology for biofuels · 2018Article
- Computational Understanding of the Selectivities in Metalloenzymes.Frontiers in chemistry · 2018Review
- Metagenomic Analysis of a Biphenyl-Degrading Soil Bacterial Consortium Reveals the Metabolic Roles of Specific Populations.Frontiers in microbiology · 2018Article
- Review
- Mechanism and selectivity of the dinuclear iron benzoyl-coenzyme A epoxidase BoxB.Chemical science · 2015Article
- Phenotypic and genotypic description of Sedimenticola selenatireducens strain CUZ, a marine (per)chlorate-respiring gammaproteobacterium, and its close relative the chlorate-respiring Sedimenticola strain NSS.Applied and environmental microbiology · 2015Article
- Benzoate metabolism intermediate benzoyl coenzyme A affects gentisate pathway regulation in Comamonas testosteroni.Applied and environmental microbiology · 2014Article
- Simultaneous catabolism of plant-derived aromatic compounds results in enhanced growth for members of the Roseobacter lineage.Applied and environmental microbiology · 2013Article
- Protein-protein interactions in the β-oxidation part of the phenylacetate utilization pathway: crystal structure of the PaaF-PaaG hydratase-isomerase complex.The Journal of biological chemistry · 2012Article
- Epoxy Coenzyme A Thioester pathways for degradation of aromatic compounds.Applied and environmental microbiology · 2012Review
- Bacterial degradation of benzoate: cross-regulation between aerobic and anaerobic pathways.The Journal of biological chemistry · 2012Article
- Article
- De-MetaST-BLAST: a tool for the validation of degenerate primer sets and data mining of publicly available metagenomes.PloS one · 2012Article
- Microbial degradation of aromatic compounds - from one strategy to four.Nature reviews. Microbiology · 2011Review
Corrections and comments
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
In the aerobic metabolism of aromatic substrates, oxygenases use molecular oxygen to hydroxylate and finally cleave the aromatic ring. In the case of the common intermediate benzoate, the ring cleavage substrates are either catechol (in bacteria) or 3,4-dihydroxybenzoate (protocatechuate, mainly in fungi). We have shown before that many bacteria, e.g. Azoarcus evansii, the organism studied here, use a completely different mechanism. This elaborate pathway requires formation of benzoyl-CoA, followed by an oxygenase reaction and a nonoxygenolytic ring cleavage. Benzoyl-CoA transformation is catalyzed by the iron-containing benzoyl-CoA oxygenase (BoxB) in conjunction with an FAD and iron-sulfur centers containing reductase (BoxA), which donates electrons from NADPH. Here we show that benzoyl-CoA oxygenase actually does not form the 2,3-dihydrodiol of benzoyl-CoA, as formerly postulated, but the 2,3-epoxide. An enoyl-CoA hydratase (BoxC) uses two molecules of water to first hydrolytically open the ring of 2,3-epoxybenzoyl-CoA, which may proceed via its tautomeric seven-membered oxepin ring form. Then ring C2 is hydrolyzed off as formic acid, yielding 3,4-dehydroadipyl-CoA semialdehyde. The semialdehyde is oxidized by a NADP(+)-dependent aldehyde dehydrogenase (BoxD) to 3,4-dehydroadipyl-CoA. Final products of the pathway are formic acid, acetyl-CoA, and succinyl-CoA. This overlooked pathway occurs in 4-5% of all bacteria whose genomes have been sequenced and represents an elegant strategy to cope with the high resonance energy of aromatic substrates by forming a nonaromatic epoxide.
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