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Catechol 1,2-DioxygenaseCatechol 2,3-DioxygenaseCatecholsDioxygenasesOxygenases4-Hydroxyphenylpyruvate DioxygenaseProtocatechuate-3,4-DioxygenaseCysteine DioxygenaseTryptophan OxygenaseEstrogens, CatecholHomogentisate 1,2-Dioxygenase3-Hydroxyanthranilate 3,4-DioxygenaseHydrocarbons, AromaticKynurenineBiodegradation, EnvironmentalPseudomonasAmino Acids, AromaticCatechol O-MethyltransferasePseudomonas putidaTryptophanRhodococcusHydroxybenzoatesChlorobenzenesTolueneSphingomonasPhenolChlorobenzoatesMixed Function OxygenasesBurkholderiaSubstrate SpecificityMolecular Sequence DataBenzoatesSorbic AcidComamonasHomogentisic AcidGentisatesBenzoic AcidAmino Acid SequenceGenes, BacterialAlcaligenesOxidation-ReductionBenzeneAdipatesCatechol OxidasePolychlorinated BiphenylsBrevibacteriumParabensCloning, MolecularPhenanthrenesKineticsHydroxylationBurkholderiaceae3-Hydroxyanthranilic Acidgamma-Butyrobetaine DioxygenaseFerredoxinsBenzene DerivativesIronAlkaptonuriaAcinetobacterKetoglutaric AcidsArthrobacterEscherichia coliRalstoniaXylenesBiphenyl CompoundsPhenolsSulfanilic AcidsVanillic AcidSequence Homology, Amino AcidBiotransformationIron-Sulfur ProteinsEnzyme InductionBacterial ProteinsPolycyclic CompoundsNaphthalenesGram-Negative Aerobic Rods and CocciFerrous CompoundsHydroquinonesBase SequenceToluidinesPlanococcus BacteriaDelftia acidovoransPyrogallolQuinolinic Acidortho-AminobenzoatesModels, MolecularSoil PollutantsCresolsSpectrophotometryStereoisomerismCatalysisSalicylatesOxidoreductasesbeta-Carotene 15,15'-MonooxygenaseEquileninSequence Analysis, DNAIntramolecular LyasesElectron Spin Resonance SpectroscopyChromatography, High Pressure LiquidTyrosinemias
HydrocarbonsDegradationEnzymeCompoundsCleavagePseudomonasBacteriaCharacterizationPolycyclicDehydrogenaseGeneSubstratesExtradiol dioxygenaseNaphthalene dioxygenaseTolueneOxidationSubstrateCatabolicStructurallyHydrolaseMetabolismPathwayAnthranilateCarbonPathwaysGenesMechanismAmino acidInvestigationReactionBioremediationAcidSpecificityMicrobiologyCytochromeReductionSeparate
Hydrocarbons7
  • 1,2-CTD degrades phenolic hydrocarbons key to the synthesis lipid membranes. (wikipedia.org)
  • Therefore, 1,2-CTD may bind to the cell lipid membrane via its terminal phospholipids and thus have greater access to the phenolic hydrocarbons vital in lipid membrane structure. (wikipedia.org)
  • Polycyclic aromatic hydrocarbons (PAHs) degrading bacteria can be isolated from polluted coastal environments. (omicsonline.org)
  • Polycyclic aromatic hydrocarbons (PAHs) are one class of organic pollutants that are considered the most hazardous due to their toxic, mutagenic, and carcinogenic properties [ 1 ]. (omicsonline.org)
  • The analysis of both the metagenome of the consortium and the reconstructed metagenome-assembled genomes show that the most abundant bacterial genus in the consortium, Acidocella , possess many of the genes required for the degradation of diesel fuel aromatic hydrocarbons, which are often the most toxic component. (springeropen.com)
  • able to significantly ( P = .05) utilize the all the aromatic hydrocarbons. (journalarrb.com)
  • and for degradation of AROMATIC HYDROCARBONS . (nih.gov)
Degradation18
  • These bacteria subsequently employ 1,2-CTD in the last step of the degradation of aromatic compounds to aliphatic products. (wikipedia.org)
  • Moreover, a dioxygenase gene, nidA3B3, was detected in Mycobacterium vanbaalenii PYR-1 as an alternate degradation pathway which could catalyze both the initial dihydroxylation of pyrene [ 11 ] to be pyrene cis-4,5-dihydrodiol, and an alternate detoxification pyrene pathway to be pyrene cis-1,2-dihydrodiol [ 12 ]. (omicsonline.org)
  • Overview: Tryptophan degradation in GapMind is based on MetaCyc degradation pathways I via anthranilate ( link ), II via pyruvate ( link ), or IX via 3-hydroxyanthranilate ( link ). (lbl.gov)
  • Comment: In MetaCyc pathway anthranilate degradation I ( link ), a dioxygenase cleaves off carbon dioxide and ammonia, leaving catechol. (lbl.gov)
  • In MetaCyc pathway anthranilate degradation IV ( link ), anthranilate hydroxylase/monooxygenase (hpaH) yields 3-hydroxyanthranilate. (lbl.gov)
  • Comment: 3-hydroxyanthranilate degradation is part of L-tryptophan degradation pathway XII ( link ). (lbl.gov)
  • Comment: In MetaCyc pathway catechol degradation to HPD I (meta-cleavage, link ), dioxygenase xylE converts catechol to (2Z,4E)-2-hydroxy-6-oxohexa-2,4-dienoate (also known as 2-hydroxymuconate 6-semialdehyde). (lbl.gov)
  • Catechol degradation to HPD II also involves xylE and HPD, link . (lbl.gov)
  • In MetaCyc pathway catechol degradation III (ortho-cleavage, link ), the 1,2-dioxygenase catA forms cis,cis-muconate, a cycloisomerase forms (+)-muconolactone, an isomerase converts this to (4,5-dihydro-5-oxofuran-2-yl)-acetate (also known as 3-oxoadipate enol lactone), and a hydrolase cleaves this to 3-oxoadipate. (lbl.gov)
  • Comment: MetaCyc pathway 3-oxoadipate degradation ( link ) involves activation by CoA (using succinyl-CoA) and a thiolase (succinyltransferase) reaction that splits it to acetyl-CoA and succinyl-CoA. (lbl.gov)
  • This series of steps is part of protocatechuate para-cleavage, link , or catechol degradation II, link . (lbl.gov)
  • This is part of a MetaCyc pathway for catechol degradation, link . (lbl.gov)
  • Comment: (2Z)-2-hydroxypenta-2,4-dienoate (HPD) is a common intermediate in the aerobic degradation of many aromatic compounds. (lbl.gov)
  • Plant-mediated effects on polycyclic aromatic hydrocarbon (PAH) degradation by bacteria in the rhizosphere of the salt marsh grasses, Spartina alterniflora and Phragmites australis. (nih.gov)
  • A number of bacteria that can degrade a variety of aromatic compounds have been identified and the pathways involved in the degradation have been extensively characterized [ 3 , 4 ]. (biomedcentral.com)
  • To explore the phylogenetic framework of bacteria isolated from contaminated marine environments of Niger Delta and the expression of the metabolic genes coding for aromatic hydrocarbon degradation and surfactant production. (journalarrb.com)
  • A laboratory scale study was carried on six composite samples of the sediment and water samples from the three studied areas using enrichment, screening, selection, characterization, and PCR assays to explore the phylogenetic framework and metabolic genes expression of the marine bacteria for aromatic hydrocarbon degradation and surfactant production. (journalarrb.com)
  • Thus, the study revealed that these bacterial strains especially Serratia marcescens XYL7 might possess metabolic genes for in situ aromatic hydrocarbon degradation and surfactant production. (journalarrb.com)
Enzyme7
  • the 1,2-CTD enzyme produced by Pseudomonas arvilla is the exception to this rule, containing two highly homologous subunits that can form either a homo- or hetero- dimer. (wikipedia.org)
  • The enzyme protocatechuate 3,4-dioxygenase (3,4-PCD) catalyzes the ring cleavage of protocatechuate (PCA) in Acinetobacter baylyi. (uni-ulm.de)
  • An aromatic compound ring cleavage enzyme of catechol 1,2-dioxygenase was detected but catechol 2,3-dioxygenase was not detected in 2C6-43 T . A fatty acid profile with anteiso-C 15: 0 , iso-C 15: 0 and C 16: 0 as the major components supported the affiliation of strain 2C6-43 T to the genus Georgenia. (elsevierpure.com)
  • PAHs could be degraded by bacteria under aerobic conditions through the initial oxidation of the aromatic ring, which is catalyzed by the dioxygenase enzyme. (omicsonline.org)
  • Specific activities of Catechol-2,3-dioxygenase and effects of temperature and pH and their stabilities on the enzyme relative activities were observed. (openmicrobiologyjournal.com)
  • An enzyme of the oxidoreductase class that catalyzes the reaction between catechol and oxygen to yield benzoquinone and water. (lookformedical.com)
  • The existence of catabolic and surfactant genes namely catechol dioxygenase ( C23O ), rhamnolipid enzyme ( rhlB ) and surfactin /lichenysin enzyme ( SrfA3 /LicA3 ) genes were detected in only four (4) out of the nine (9) marine aromatic degrading bacteria with 881 base pairs sizes. (journalarrb.com)
Compounds7
  • low-molecular-weight (LMW) compounds consist of two or three rings, and high-molecular-weight (HMW) compounds, more than three rings [ 3 ]. (omicsonline.org)
  • Benzene compounds with dihydroxylated rings, e.g. catechol (1,2-benzenediol) and hydroquinone (1,4-benzenediol), are important intermediates in bacterial catabolism of aromatic compounds. (ethz.ch)
  • They play a key role in the metabolism of organic compounds by increasing their reactivity or water solubility or bringing about cleavage of the aromatic ring. (biomedcentral.com)
  • Many of these compounds have been reported to be toxic to the living organisms [ 3 ]. (biomedcentral.com)
  • In the convergent mode, structurally diverse aromatic compounds are converted to one of a few aromatic ring cleavage substrates such as catechol, gent sate, protocatechuate and their derivatives [ 5 ]. (biomedcentral.com)
  • Some of the enzymes which generate aromatic radicals that break down most prominent bacterial strains found were isolated and tax- the complex linkages present in lignin to compounds of lower onomically identified using 16S ribosomal RNA (rRNA) se- molecular weight. (lu.se)
  • Two compounds, Compound 1 (1,4-dihydrophenanthrolin-4-one-3-carboxylic acid) and Compound 5 [8-(N-butyl-N-ethylcarbamoyl)-1,4-dihydrophenathrolin-4-one-3-carboxylic acid], with comparable potencies in vivo, were chosen to investigate the effect of the inhibition of the hydroxylation of newly synthesized uterine collagen on the turnover of this protein in vivo. (embl.de)
Cleavage2
  • 2021. Separate upper pathway ring cleavage dioxygenases are required for growth of Sphingomonas wittichii strain RW1 on dibenzofuran and dibenzo-p-dioxin. (nih.gov)
  • In this divergent mode, a metal-dependent dioxygenase channels these dihydroxylated intermediates into one of the two possible pathways: the meta -cleavage pathway or the ortho -cleavage pathway [ 7 - 9 ] (Fig. 1 ). (biomedcentral.com)
Pseudomonas8
Bacteria1
  • Peripheral enzymes, particularly oxygenases and dehydrogenases, were found to transform structurally diverse substrates into one of these central intermediates by bringing about the hydroxylation of the aromatic nucleus (Fig. 2A ), and hence it is thought that bacteria have developed these enzymes to extend their substrate range [ 5 ]. (biomedcentral.com)
Characterization3
  • 2003. Characterization of a novel Acinetobacter species containing a toluene dioxygenase. (nih.gov)
  • Substrate specificity of catechol oxidase from Lycopus europaeus and characterization of the bioproducts of enzymic caffeic acid oxidation. (lookformedical.com)
  • 1. Fischer, D., Ebenau-Jehle, C. and Grisebach, H. Phytoalexin synthesis in soybean: purification and characterization of NADPH:2'-hydroxydaidzein oxidoreductase from elicitor-challenged soybean cell cultures. (qmul.ac.uk)
Polycyclic1
  • 2006. Microbial dioxygenase gene population shifts during polycyclic aromatic hydrocarbon biodegradation. (nih.gov)
Dehydrogenase4
  • Dioxygenase NbaC cleaves the aromatic ring, yielding 2-amino-3-carboxymuconate 6-semialdehyde, a decarboxylase forms (2Z,4E)-2-aminomuconate semialdehyde, a dehydrogenase forms (2Z,4E)-2-aminomuconate, a deaminase forms (3E)-2-oxo-3-hexenedioate (also known as 2-oxalocrotonate), and a decarboxylase forms (2Z)-2-hydroxypenta-2,4-dienoate (HPD). (lbl.gov)
  • Comment: Dehydrogenase praB forms 2-hydroxymuconate, tautomerase praC forms (3E)-2-oxohex-3-enedioate (2-oxalocrotonate), and decarboxylase praD yields 2-hydroxypenta-2,4-dienoate (HPD). (lbl.gov)
  • p-Xylene-grown cells contained an inducible NAD+-dependent dehydrogenase which formed catechols from cis-p-toluate diol and the analogous acid diols formed from the other hydrocarbon substrates listed above. (rhea-db.org)
  • aldehyde dehydrogenase 2 family member. (gsea-msigdb.org)
Gene3
  • 6 identified a gene cluster, hbpCAD , encoding the upper metabolic pathway of OPP which involves the transformation of OPP to 2-hydroxypenta-2,4-dienoateand benzoic acid (BA). (nature.com)
  • For all significantly differentially expressed microRNAs inside of the 2 groups, we now have produced gene sets from their expressed target genes. (pdpksignaling.com)
  • Catechol 2,3-dioxygenase (C23O) gene was found andamplified with the designed primers from the total DNA of C-14-1. (researchgate.net)
Substrates3
  • In A. baylyi this mechanism was investigated using the degradative pathways for the aromatic substrates and dicarboxylates. (uni-ulm.de)
  • Oxygenases belong to the oxidoreductive group of enzymes (E.C. Class 1), which oxidize the substrates by transferring oxygen from molecular oxygen (O 2 ) and utilize FAD/NADH/NADPH as the co-substrate. (biomedcentral.com)
  • Substrates containing a -COOH group are inhibitors for catechol oxidase. (lookformedical.com)
Extradiol dioxygenase1
  • The two enzymes were identified to be a part of two separate catechol dioxygenase families: 1,2-CTD was classified as an intradiol dioxygenase while 2,3-CTD was classified as an extradiol dioxygenase. (wikipedia.org)
Naphthalene dioxygenase2
  • Crystal structure of naphthalene dioxygenase: side-on binding of dioxygen to iron. (research.com)
  • An integrated approach of bioassay and molecular docking to study the dihydroxylation mechanism of pyrene by naphthalene dioxygenase in Rhodococcus sp. (brenda-enzymes.org)
Toluene1
Oxidation1
Substrate3
Catabolic2
  • For example, pathway IV yields indole-3-lactate, which could potentially be oxidized to indole-3-acetate, which has a known catabolic pathway, but no prokaryotes are known to consume tryptophan this way. (lbl.gov)
  • The second ben/cat operon was located in a 92-kb scaffold along with (i) an operon ( opp ) comprising genes for the transformation of OPP to BA and 2-hydroxypenta-2,4-dienoate (and genes for its transformation) and (ii) an incomplete biphenyl catabolic operon ( bph ). (nature.com)
Structurally1
  • Catechol 1,2-dioxygenase is structurally similar to 3,4-PCD. (uni-ulm.de)
Hydrolase1
  • Comment: In pathway I, dioxygenase kynA opens the non-aromatic ring, to N-formyl-L-kynureine, a hydrolase yields L-kynurenine (and formate), and a hydrolase yields anthranilate and L-alanine. (lbl.gov)
Metabolism2
  • The bacterial catabolism of orcinol (5-methyl-1,3-benzenediol) can be used as a model for the metabolism of other members of the resorcinol (1,3-benzenediol) compound family. (ethz.ch)
  • These results contribute to a better more biomass-derived carbohydrates are also used for produc- understanding of the aromatic metabolism of P. putida in tion of chemicals, a further valorization of lignin is an essential terms of growth and uptake rates, which will be helpful for component. (lu.se)
Pathway2
  • The pcaH was significant in the β-ketoadipate pathway [9] where the pathway as it conserves biochemically, and is a major class of non-heme-iron containing dioxygenase [ 10 ]. (omicsonline.org)
  • Pathway VIII yields tryptophol (also known as indole-3-ethanol), which could potentially be oxidized to indole-3-acetate and consumed. (lbl.gov)
Anthranilate1
  • Comment: There are two forms of anthranilate dioxygenase, 3-subunit antABC or 4-subunit andAabcd. (lbl.gov)
Carbon4
  • 1,2-CTD uses Fe3+ as a cofactor to cleave the carbon-carbon bond between the phenolic hydroxyl groups of catechol, thus yielding muconic acid as its product. (wikipedia.org)
  • In contrast, 2,3-CTD utilizes Fe2+ as a cofactor to cleave the carbon-carbon bond adjacent to the phenolic hydroxyl groups of catechol, thus yielding 2-hydroxymuconaldehye as its product. (wikipedia.org)
  • The second catechol hydroxyl group on carbon 3 (C3) is coordinated to Fe3+ after its deprotonation by the Tyr200 ligand. (wikipedia.org)
  • This is a key step in the breakdown of a large number of aromatic carbon sources. (uni-ulm.de)
Pathways2
  • Pathways X and XIII yield indole-3-propionate, which may spontaneously oxidize to kynurate, but kynurate catabolism is not reported. (lbl.gov)
  • Additional pathways are not included: the fate of 2-amino-5-oxocyclohex-1-enecarboxyl-CoA is not known ( link ), and anthraniloyl-CoA reductase (the only anaerobic route known, link ) has not been linked to sequence. (lbl.gov)
Genes2
  • nidA and nidB genes are encoding genes for large and small subunits of napthalene-inducible dioxygenase [ 7 , 8 ]. (omicsonline.org)
  • B, solute carrier relatives six member 2, solute carrier relatives 18 member one, and transcription factors and homeobox genes involved in neural crest derived cell de velopment, paired like homeobox 2a and 2b, GATA binding protein two and 3, heart and neural crest derivatives expressed two. (pdpksignaling.com)
Mechanism1
Amino acid1
  • l -3,4-dihydroxyphenylalanine , is an amino acid that is made and used as part of the normal biology of some plants [3] and animals, including humans. (cloudfront.net)
Investigation1
  • In this investigation, random PCR mutagenesis has been carried out to explore the functional role of the R133 in 3,4-PCD. (uni-ulm.de)
Reaction1
  • In the reverse reaction, the 2'-hydroxyisoflavone (2'-hydroxydaidzein) is reduced to an isoflavanone. (qmul.ac.uk)
Bioremediation1
Acid1
  • Treatment of P. putida BG1 with nitrosoguanidine led to the isolation of a mutant strain which, when grown with fructose, oxidized both p-xylene and p-toluate to (-)-cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylic acid (cis-p-toluate diol). (rhea-db.org)
Specificity1
  • However, studies could show that a R133H substitution switches the specificity of 3,4-PCD towards catechol. (uni-ulm.de)
Microbiology1
Cytochrome1
Reduction2
  • this has seen reduction in SO 2 emissions across Europe by more than 60% between 1990 and 2004 (Vestreng et al. (springer.com)
  • reproductive enthusiastic feed 's the Common reduction of 1,3-diaminobenzenes from entirely gradual risks. (xn--drpverein-rahe-vpb.de)
Separate1