Cytochrome P450 induced formation of hydroxylated polybrominated diphenyl ether and dibenzo-p-dioxin derivates from brominated phenols DOI Creative Commons
Sina Schweizer, Benjamin Aberle, Alexandra Klimm

и другие.

The Science of The Total Environment, Год журнала: 2024, Номер 958, С. 177940 - 177940

Опубликована: Дек. 10, 2024

Methoxylated polybrominated diphenyl ethers (MeO-BDEs) are a class of environmentally relevant halogenated natural products. The two most isomers, 2'-MeO-BDE 68 and 6-MeO-BDE 47, were repeatedly detected at levels comparable with persistent organic pollutants in marine environmental food samples. MeO-BDEs suspected to be biosynthesized by bromoperoxidases through the merging bromophenol units, three which (2,4-dibromophenol, 2,6-dibromophenol 2,4,6-tribromophenol) abundant environments, followed O-methylation give MeO-BDEs. However, not all can explained direct coupling bromophenols. Therefore, several bromophenols incubated CYP109B1 from Bacillus subtilis. Incubations 2,4-dibromophenol resulted both 2'-OH-BDE 6-OH-BDE 47. Mechanistic considerations indicated that compounds emerged an epoxidized intermediate. After subsequent methylation this leads environments. By contrast, incubations 2,4,6-tribromophenol did form any OH-BDEs but tri- or tetrabrominated dibenzo-p-dioxins (PBDDs), i.e. another known products whose toxicity has shown similar their chlorinated analogues. SYNOPSIS: Treatment cytochrome P450 monooxygenase led formation hydroxylated dibenzo-p-dioxins.

Язык: Английский

Characterization and Description of Anaeromyxobacter dehalogenans gen. nov., sp. nov., an Aryl-Halorespiring Facultative Anaerobic Myxobacterium DOI
Robert A. Sanford,

James R. Cole,

James M. Tiedje

и другие.

Applied and Environmental Microbiology, Год журнала: 2002, Номер 68(2), С. 893 - 900

Опубликована: Фев. 1, 2002

ABSTRACT Five strains were isolated which form a physiologically and phylogenetically coherent group of chlororespiring microorganisms represent the first taxon in Myxobacteria capable anaerobic growth. The enriched from various soils sediments based on their ability to grow using acetate as an electron donor 2-chlorophenol (2-CPh) acceptor. They are slender gram-negative rods with bright red pigmentation that exhibit gliding motility spore-like structures. These unique myxobacteria also 2,6-dichlorophenol, 2,5-dichlorophenol, 2-bromophenol, nitrate, fumarate, oxygen terminal acceptors, optimal growth occurring at low concentrations (<1 mM) 2-CPh is reduced by all acceptor preference ammonium. Acetate, H 2 , succinate, pyruvate, formate, lactate used donors. None grew fermentation. 16S ribosomal DNA (rDNA) sequences five cluster deeply branching within family Myxococcaceae class mostly closely associated Myxococcus subgroup. With exception lack characteristic fruiting body, these resemble previously characterized therefore should be considered part 9.0% difference rDNA sequence those other myxobacterial genera sufficient place new genus species designated Anaeromyxobacter dehalogenans . type strain 2CP-1 (ATCC BAA-258).

Язык: Английский

Процитировано

365

Characterization of Two Tetrachloroethene-Reducing, Acetate-Oxidizing Anaerobic Bacteria and Their Description asDesulfuromonas michiganensissp. nov DOI Open Access

Youlboong Sung,

Kirsti M. Ritalahti,

Robert A. Sanford

и другие.

Applied and Environmental Microbiology, Год журнала: 2003, Номер 69(5), С. 2964 - 2974

Опубликована: Май 1, 2003

ABSTRACT Two tetrachlorethene (PCE)-dechlorinating populations, designated strains BB1 and BRS1, were isolated from pristine river sediment chloroethene-contaminated aquifer material, respectively. PCE-to- cis -1,2-dichloroethene-dechlorinating activity could be transferred in defined basal salts medium with acetate as the electron donor PCE acceptor. Taxonomic analysis based on 16S rRNA gene sequencing placed both isolates within Desulfuromonas cluster δ subdivision of Proteobacteria . was dechlorinated at rates least 139 nmol min −1 mg protein pH values between 7.0 7.5 temperatures 25 30°C. Dechlorination also occurred 10°C. The donors that supported dechlorination included acetate, lactate, pyruvate, succinate, malate, fumarate but not hydrogen, formate, ethanol, propionate, or sulfide. Growth malate alone, whereas oxidation other depended strictly presence fumarate, ferric iron, sulfur, PCE, TCE an Nitrate, sulfate, sulfite, thiosulfate, chlorinated compounds used acceptors. Sulfite had a strong inhibitory effect growth dechlorination. Alternate acceptors (e.g., iron) did inhibit consumed concomitantly. putative iron reductases induced by their respective substrates constitutively present. Sulfide required for growth. Both tolerated high concentrations free-phase (dense non-aqueous-phase liquids). Repeated yielded variant lost ability to dechlorinate PCE. Due sequence differences closest relatives unique phenotypic characteristics, we propose new are members species, michiganensis , Geobacteraceae

Язык: Английский

Процитировано

231

Deep Electroreductive Chemistry: Harnessing Carbon- and Silicon-Based Reactive Intermediates in Organic Synthesis DOI Open Access
Wen Zhang, Weiyang Guan, Jesus I. Martinez Alvarado

и другие.

ACS Catalysis, Год журнала: 2023, Номер 13(12), С. 8038 - 8048

Опубликована: Май 31, 2023

ADVERTISEMENT RETURN TO ISSUEPREVViewpointNEXTDeep Electroreductive Chemistry: Harnessing Carbon- and Silicon-Based Reactive Intermediates in Organic SynthesisWen ZhangWen ZhangDepartment of Chemistry Chemical Biology, Cornell University, Ithaca, New York 14853, United StatesMore by Wen Zhanghttps://orcid.org/0000-0002-0704-3463, Weiyang GuanWeiyang GuanDepartment Guan, Jesus I. Martinez AlvaradoJesus AlvaradoDepartment Alvarado, Luiz F. T. NovaesLuiz NovaesDepartment Novaeshttps://orcid.org/0000-0003-1209-2865, Song Lin*Song LinDepartment States*Email: [email protected]More Linhttps://orcid.org/0000-0002-8880-6476Cite this: ACS Catal. 2023, 13, 12, 8038–8048Publication Date (Web):May 31, 2023Publication History Received14 March 2023Published online31 May inissue 16 June 2023https://pubs.acs.org/doi/10.1021/acscatal.3c01174https://doi.org/10.1021/acscatal.3c01174article-commentaryACS PublicationsCopyright © 2023 American Society. This publication is available under these Terms Use. Request reuse permissions free to access through this site. Learn MoreArticle Views8051Altmetric-Citations5LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum full text article downloads since November 2008 (both PDF HTML) across all institutions individuals. These metrics regularly updated reflect usage leading up last few days.Citations number other articles citing article, calculated Crossref daily. Find more information about citation counts.The Altmetric Attention Score a quantitative measure attention that research has received online. Clicking on donut icon will load page at altmetric.com with additional details score social media presence for given article. how calculated. Share Add toView InAdd Full Text ReferenceAdd Description ExportRISCitationCitation abstractCitation referencesMore Options onFacebookTwitterWechatLinked InRedditEmail (3 MB) Get e-AlertscloseSUBJECTS:Alkyls,Anions,Halogens,Hydrocarbons,Inorganic compounds e-Alerts

Язык: Английский

Процитировано

27

Isolation and Characterization of Desulfovibrio dechloracetivorans sp. nov., a Marine Dechlorinating Bacterium Growing by Coupling the Oxidation of Acetate to the Reductive Dechlorination of 2-Chlorophenol DOI
Baolin Sun,

James R. Cole,

Robert A. Sanford

и другие.

Applied and Environmental Microbiology, Год журнала: 2000, Номер 66(6), С. 2408 - 2413

Опубликована: Июнь 1, 2000

ABSTRACT Strain SF3, a gram-negative, anaerobic, motile, short curved rod that grows by coupling the reductive dechlorination of 2-chlorophenol (2-CP) to oxidation acetate, was isolated from San Francisco Bay sediment. SF3 grew at concentrations NaCl ranging 0.16 2.5%, but KCl above 0.32% inhibited growth. The isolate used fumarate, lactate, propionate, pyruvate, alanine, and ethanol as electron donors for growth coupled dechlorination. Among halogenated aromatic compounds tested, only ortho position chlorophenols reductively dechlorinated, additional chlorines other positions blocked Sulfate, sulfite, thiosulfate, nitrate were also acceptors optimal temperature 30°C, no or activity observed 37°C. Growth revealed yield about 1 g protein per mol 2-CP 2.7 mole 2,6-dichlorophenol dechlorinated. physiological features 16S ribosomal DNA sequence suggest organism is novel species genus Desulfovibrio which we have designated dechloracetivorans . unusual feature this strain it uses acetate an donor carbon source with not sulfate.

Язык: Английский

Процитировано

147

Enediyne natural product biosynthesis unified by a diiodotetrayne intermediate DOI
Chun Gui, Edward Kalkreuter, Lukas Lauterbach

и другие.

Nature Chemical Biology, Год журнала: 2024, Номер 20(9), С. 1210 - 1219

Опубликована: Июнь 3, 2024

Язык: Английский

Процитировано

6

High Levels of Endemicity of 3-Chlorobenzoate-Degrading Soil Bacteria DOI Open Access
Roberta R. Fulthorpe,

Albert N. Rhodes,

James M. Tiedje

и другие.

Applied and Environmental Microbiology, Год журнала: 1998, Номер 64(5), С. 1620 - 1627

Опубликована: Май 1, 1998

Soils samples were obtained from pristine ecosystems in six regions on five continents. Two of the boreal forests, and other four Mediterranean ecosystems. Twenty-four soil each or sites enriched by using 3-chlorobenzoate (3CBA), 3CBA mineralizers isolated most samples. These isolates analyzed for ability to mineralize 3CBA, genotypes determined with repetitive extragenic palindromic PCR genomic fingerprints restriction digests 16S rRNA genes (amplified ribosomal DNA analysis [ARDRA]). We found that our collection 150 stable 3CBA-mineralizing included 48 44 ARDRA types, which formed seven distinct clusters. The majority (91%) unique they isolated, genotype was only region it isolated. A total 43 types one region. few repeatedly but not any continental region, suggesting are regionally endemic. correlation between bacterial vegetative community South African results suggest is distributed among very diverse globally dispersed.

Язык: Английский

Процитировано

121

Laccase Catalyzed Synthesis of Iodinated Phenolic Compounds with Antifungal Activity DOI Creative Commons

Julian Ihssen,

Mark Schubert,

Linda Thöny‐Meyer

и другие.

PLoS ONE, Год журнала: 2014, Номер 9(3), С. e89924 - e89924

Опубликована: Март 3, 2014

Iodine is a well known antimicrobial compound. Laccase, an oxidoreductase which couples the one electron oxidation of diverse phenolic and non-phenolic substrates to reduction oxygen water, capable oxidizing unreactive iodide reactive iodine. We have shown previously that laccase-iodide treatment spruce wood results in wash-out resistant surface. In this study, we investigated whether compounds such as vanillin, resembles sub-structures softwood lignin, can be directly iodinated by reacting with laccase iodide, resulting antifungal activity. HPLC-MS analysis showed vanillin was converted iodovanillin catalysis at excess potassium iodide. No conversion occurred absence enzyme. The addition redox mediators catalytic concentrations increased rate ten-fold yield 50%. Iodinated products were also detected when o-vanillin, ethyl acetovanillone methyl vanillate incubated At educt concentration 0.1 M almost molar ratio could used without compromising rate, insoluble product recovered simple centrifugation. novel enzymatic synthesis procedure fulfills key criteria green chemistry. Biocatalytically produced iodo-ethyl had significant growth inhibitory effects on several degrading fungal species. For Trametes versicolor, species causing white rot wood, complete inhibition partial biocidal effect observed agar plates. Enzymatic tests indicated acted enzyme responsive, materials.

Язык: Английский

Процитировано

56

Photic versus Aphotic Production of Organohalogens from Native versus Invasive Wetland Plants-Derived Dissolved Organic Matter DOI
Yu Fu,

Xueqi Hu,

Pu Wang

и другие.

Water Research, Год журнала: 2025, Номер 274, С. 123103 - 123103

Опубликована: Янв. 7, 2025

Язык: Английский

Процитировано

0

A metagenomic-based survey of microbial (de)halogenation potential in a German forest soil DOI Creative Commons

Pascal Weigold,

Mohamed El-Hadidi,

Alexander Ruecker

и другие.

Scientific Reports, Год журнала: 2016, Номер 6(1)

Опубликована: Июнь 29, 2016

Abstract In soils halogens (fluorine, chlorine, bromine, iodine) are cycled through the transformation of inorganic halides into organohalogen compounds and vice versa. There is evidence that these reactions microbially driven but key enzymes groups microorganisms involved largely unknown. Our aim was to uncover diversity, abundance distribution genes encoding for halogenating dehalogenating in a German forest soil by shotgun metagenomic sequencing. Metagenomic libraries three horizons revealed presence genera known be halogenation dehalogenation processes such as Bradyrhizobium or Pseudomonas . We detected so far unknown diversity (de)halogenating metagenome including specific unspecific halogenases well metabolic cometabolic dehalogenases. Genes non-heme, no-metal chloroperoxidases haloalkane dehalogenases were most abundant halogenase dehalogenase genes, respectively. The high suggests strong microbial contribution natural halogen cycling. This also confirmed microcosm experiments which we quantified biotic formation chloroform bromoform. Knowledge on catalyze (de)halogenation critical because they highly relevant industrial biotechnologies bioremediation applications.

Язык: Английский

Процитировано

43

Lewis Base-Catalyzed Interhalogenation of Terminal Allenes: Selective Strategy for Accessing Vicinal Vinylic, Allylic Heterodihalides DOI

Alexandra E. Lubaev,

Favour Eze,

Manjula D. Rathnayake

и другие.

Organic Letters, Год журнала: 2025, Номер unknown

Опубликована: Март 28, 2025

Though precedent remains limited, the selective interhalogenation of allenes offers a valuable synthetic strategy to access products where each halide exhibits orthogonal reactivity. Here, we describe Lewis base-catalyzed approach for dihalogenation (bromochlorination, iodochlorination, iodobromination, and dibromination) terminal allenes. By employing just 1 mol % triphenylphosphine oxide or hexamethylphosphoramide activate thionyl halides in presence electrophilic halogenation reagents, achieve conversion monosubstituted vicinal allylic, vinylic dihalides with up 93% yield >20:1 regioisomeric ratio, favoring branched dihalogenated product. A range functional groups is tolerated, including nitrile, ester, phosphate, sulfonamide, silyl groups, reaction proved be scalable. The utility various dihalide was investigated substitution cross-coupling chemistry, highlighting distinct reactivity among different classes.

Язык: Английский

Процитировано

0