Naphthalene Carboxylation in the Sulfate-Reducing Enrichment Culture N47 Is Proposed to Proceed via 1,3-Dipolar Cycloaddition to the Cofactor Prenylated Flavin Mononucleotide

Heker, Isabelle; Haberhauer, Gebhard

doi:10.1128/aem.01927-22

Cited by 3 publications

(3 citation statements)

References 52 publications

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“…Moreover, MAG 34 encodes four copies of naphthoyl-CoA ligase (NCL) highly homologous to the variants of NaphS2 and N47 (amino acid identity ≥67%). NCL converts 2-naphthoate to 2-naphthoyl-CoA (Heker et al, 2023). Further, it is capable of the three-step RD of naphthalene, encoding homologues of 2-naphtoyl-CoA reductase (NCR), 5,6-dihydro-2-naphthoyl-CoA reductase (DHNCR), and both N47 and NaphS2 type of 5,6,7,8-tetrahydro-2-naphthoyl-CoA reductase (THNCR).…”

Section: Uah Degradation Pathways In Abundant Magsmentioning

confidence: 99%

“…Like for benzene, direct carboxylation is the likely activation mechanism for naphthalene in most cultures (Galushko et al, 1999;Musat et al, 2009;DiDonato et al, 2010;Kleemann and Meckenstock, 2011;Mouttaki et al, 2012;Kümmel et al, 2015). A gene cluster encoding a putative naphthalene carboxylase complex, including UbiD-like carboxylases similar to AbcA, has been described (Kümmel et al, 2015;Koelschbach et al, 2019;Heker et al, 2023). Subsequent degradation occurs via conversion to 2-naphthoyl-CoA (Bergmann F. D. et al, 2011;Meckenstock et al, 2016;Heker et al, 2023) and a three-step reductive dearomatization (Eberlein et al, 2013a,b;Estelmann et al, 2015;Meckenstock et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

“…A gene cluster encoding a putative naphthalene carboxylase complex, including UbiD-like carboxylases similar to AbcA, has been described (Kümmel et al, 2015;Koelschbach et al, 2019;Heker et al, 2023). Subsequent degradation occurs via conversion to 2-naphthoyl-CoA (Bergmann F. D. et al, 2011;Meckenstock et al, 2016;Heker et al, 2023) and a three-step reductive dearomatization (Eberlein et al, 2013a,b;Estelmann et al, 2015;Meckenstock et al, 2016). A stepwise oxidation, which includes ring cleavage and removal of branched alkyl chains, produces acetyl-CoA, presumably by enzymes encoded in the thn operon which is found in NaphS2 and N47 (Meckenstock et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

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Potential for the anaerobic oxidation of benzene and naphthalene in thermophilic microorganisms from the Guaymas Basin

Zehnle,

Otersen,

Benito Merino

et al. 2023

Front. Microbiol.

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Unsubstituted aromatic hydrocarbons (UAHs) are recalcitrant molecules abundant in crude oil, which is accumulated in subsurface reservoirs and occasionally enters the marine environment through natural seepage or human-caused spillage. The challenging anaerobic degradation of UAHs by microorganisms, in particular under thermophilic conditions, is poorly understood. Here, we established benzene- and naphthalene-degrading cultures under sulfate-reducing conditions at 50°C and 70°C from Guaymas Basin sediments. We investigated the microorganisms in the enrichment cultures and their potential for UAH oxidation through short-read metagenome sequencing and analysis. Dependent on the combination of UAH and temperature, different microorganisms became enriched. A Thermoplasmatota archaeon was abundant in the benzene-degrading culture at 50°C, but catabolic pathways remained elusive, because the archaeon lacked most known genes for benzene degradation. Two novel species of Desulfatiglandales bacteria were strongly enriched in the benzene-degrading culture at 70°C and in the naphthalene-degrading culture at 50°C. Both bacteria encode almost complete pathways for UAH degradation and for downstream degradation. They likely activate benzene via methylation, and naphthalene via direct carboxylation, respectively. The two species constitute the first thermophilic UAH degraders of the Desulfatiglandales. In the naphthalene-degrading culture incubated at 70°C, a Dehalococcoidia bacterium became enriched, which encoded a partial pathway for UAH degradation. Comparison of enriched bacteria with related genomes from environmental samples indicated that pathways for benzene degradation are widely distributed, while thermophily and capacity for naphthalene activation are rare. Our study highlights the capacities of uncultured thermophilic microbes for UAH degradation in petroleum reservoirs and in contaminated environments.

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Section: Uah Degradation Pathways In Abundant Magsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Potential for the anaerobic oxidation of benzene and naphthalene in thermophilic microorganisms from the Guaymas Basin

Zehnle,

Otersen,

Benito Merino

et al. 2023

Front. Microbiol.

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Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

Mondal,

Roy,

Carrannanto

et al. 2024

Faraday Discuss.

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A CoA‐Transferase and Acyl‐CoA Dehydrogenase Convert 2‐(Carboxymethyl)cyclohexane‐1‐Carboxyl‐CoA During Anaerobic Naphthalene Degradation

Kong,

Riebe,

Feßner

et al. 2024

Environmental Microbiology

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The CoA thioester of 2‐(carboxymethyl)cyclohexane‐1‐carboxylic acid has been identified as a metabolite in anaerobic naphthalene degradation by the sulfate‐reducing culture N47. This study identified and characterised two acyl‐CoA dehydrogenases (ThnO/ThnT) and an intramolecular CoA‐transferase (ThnP) encoded within the substrate‐induced thn operon, which contains genes for anaerobic degradation of naphthalene. ThnP is a CoA transferase belonging to the family I (Cat 1 subgroup) that catalyses the intramolecular CoA transfer from the carboxyl group of 2‐(carboxymethyl)cyclohexane‐1‐carboxyl‐CoA to its carboxymethyl moiety, forming 2‐carboxycyclohexylacetyl‐CoA. Neither acetyl‐CoA nor succinyl‐CoA functions as an exogenous CoA donor for this reaction. The flavin‐dependent homotetrameric dehydrogenase ThnO is specific for (1R,2R)‐2‐carboxycyclohexylacetyl‐CoA with an apparent Km value of 61.5 μM, whereas ThnT is a promiscuous enzyme catalysing the same reaction at lower rates. Identifying these three enzymes confirmed the involvement of the thn gene cluster in the anaerobic naphthalene degradation pathway. This study establishes a modified metabolic pathway for anaerobic naphthalene degradation upstream of 2‐(carboxymethyl)cyclohexane‐1‐carboxyl‐CoA and provides further insight into the subsequent second‐ring cleavage reaction.

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Naphthalene Carboxylation in the Sulfate-Reducing Enrichment Culture N47 Is Proposed to Proceed via 1,3-Dipolar Cycloaddition to the Cofactor Prenylated Flavin Mononucleotide

Cited by 3 publications

References 52 publications

Potential for the anaerobic oxidation of benzene and naphthalene in thermophilic microorganisms from the Guaymas Basin

Potential for the anaerobic oxidation of benzene and naphthalene in thermophilic microorganisms from the Guaymas Basin

Surveying the scope of aromatic decarboxylations catalyzed by prenylated-flavin dependent enzymes

A CoA‐Transferase and Acyl‐CoA Dehydrogenase Convert 2‐(Carboxymethyl)cyclohexane‐1‐Carboxyl‐CoA During Anaerobic Naphthalene Degradation

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