Bibliographies thématiques / Biphenyl 2-hydroxylation

Littérature scientifique sur le sujet « Biphenyl 2-hydroxylation »

Auteur : Grafiati
Publié le 25 juillet 2024
Mis à jour le 26 juillet 2024

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Articles de revues sur le sujet "Biphenyl 2-hydroxylation"

1

Duan, Shitao, Yuanshuang Xu, Xinying Zhang et Xuesen Fan. « Synthesis of 2,2′-biphenols through direct C(sp2)–H hydroxylation of [1,1′-biphenyl]-2-ols ». Chemical Communications 52, no 69 (2016) : 10529–32. http://dx.doi.org/10.1039/c6cc04756d.

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A novel synthesis of diversely substituted 2,2′-biphenols through Pd(ii)-catalyzed,tBuOOH-oxidized, and hydroxyl-directed C(sp2)–H hydroxylation of [1,1′-biphenyl]-2-ols has been developed.
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Pham, Thi Thanh My, Mohammad Sondossi et Michel Sylvestre. « Metabolism of Doublypara-Substituted Hydroxychlorobiphenyls by Bacterial Biphenyl Dioxygenases ». Applied and Environmental Microbiology 81, no 14 (8 mai 2015) : 4860–72. http://dx.doi.org/10.1128/aem.00786-15.

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ABSTRACTIn this work, we examined the profile of metabolites produced from the doublypara-substituted biphenyl analogs 4,4′-dihydroxybiphenyl, 4-hydroxy-4′-chlorobiphenyl, 3-hydroxy-4,4′-dichlorobiphenyl, and 3,3′-dihydroxy-4,4′-chlorobiphenyl by biphenyl-inducedPandoraea pnomenusaB356 and by its biphenyl dioxygenase (BPDO). 4-Hydroxy-4′-chlorobiphenyl was hydroxylated principally through a 2,3-dioxygenation of the hydroxylated ring to generate 2,3-dihydro-2,3,4-trihydroxy-4′-chlorobiphenyl and 3,4-dihydroxy-4′-chlorobiphenyl after the removal of water. The former was further oxidized by the biphenyl dioxygenase to produce ultimately 3,4,5-trihydroxy-4′-chlorobiphenyl, a dead-end metabolite. 3-Hydroxy-4,4′-dichlorobiphenyl was oxygenated on both rings. Hydroxylation of the nonhydroxylated ring generated 2,3,3′-trihydroxy-4′-chlorobiphenyl with concomitant dechlorination, and 2,3,3′-trihydroxy-4′-chlorobiphenyl was ultimately metabolized to 2-hydroxy-4-chlorobenzoate, but hydroxylation of the hydroxylated ring generated dead-end metabolites. 3,3′-Dihydroxy-4,4′-dichlorobiphenyl was principally metabolized through a 2,3-dioxygenation to generate 2,3-dihydro-2,3,3′-trihydroxy-4,4′-dichlorobiphenyl, which was ultimately converted to 3-hydroxy-4-chlorobenzoate. Similar metabolites were produced when the biphenyl dioxygenase ofBurkholderia xenovoransLB400 was used to catalyze the reactions, except that for the three substrates used, the BPDO of LB400 was less efficient than that of B356, and unlike that of B356, it was unable to further oxidize the initial reaction products. Together the data show that BPDO oxidation of doublypara-substituted hydroxychlorobiphenyls may generate nonnegligible amounts of dead-end metabolites. Therefore, biphenyl dioxygenase could produce metabolites other than those expected, corresponding to dihydrodihydroxy metabolites from initial doublypara-substituted substrates. This finding shows that a clear picture of the fate of polychlorinated biphenyls in contaminated sites will require more insights into the bacterial metabolism of hydroxychlorobiphenyls and the chemistry of the dihydrodihydroxylated metabolites derived from them.
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Gesell, Manuela, Elke Hammer, Michael Specht, Wittko Francke et Frieder Schauer. « Biotransformation of Biphenyl by Paecilomyces lilacinus and Characterization of Ring Cleavage Products ». Applied and Environmental Microbiology 67, no 4 (1 avril 2001) : 1551–57. http://dx.doi.org/10.1128/aem.67.4.1551-1557.2001.

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ABSTRACT We examined the pathway by which the fungicide biphenyl is metabolized in the imperfect fungus Paecilomyces lilacinus. The initial oxidation yielded the three monohydroxylated biphenyls. Further hydroxylation occurred on the first and the second aromatic ring systems, resulting in the formation of five di- and trihydroxylated metabolites. The fungus could cleave the aromatic structures, resulting in the transformation of biphenyl viaortho-substituted dihydroxybiphenyl to six-ring fission products. All compounds were characterized by gas chromatography-mass spectroscopy and proton nuclear magnetic resonance spectroscopy. These compounds include 2-hydroxy-4-phenylmuconic acid and 2-hydroxy-4-(4′-hydroxyphenyl)-muconic acid, which were produced from 3,4-dihydroxybiphenyl and further transformed to the corresponding lactones 4-phenyl-2-pyrone-6-carboxylic acid and 4-(4′-hydroxyphenyl)-2-pyrone-6-carboxylic acid, which accumulated in large amounts. Two additional ring cleavage products were identified as (5-oxo-3-phenyl-2,5-dihydrofuran-2-yl)-acetic acid and [5-oxo-3-(4′-hydroxyphenyl)-2,5-dihydrofuran-2-yl]-acetic acid. We found that P. lilacinus has a high transformation capacity for biphenyl, which could explain this organism's tolerance to this fungicide.
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Sondossi, M., D. Barriault et M. Sylvestre. « Metabolism of 2,2′- and 3,3′-Dihydroxybiphenyl by the Biphenyl Catabolic Pathway of Comamonas testosteroni B-356 ». Applied and Environmental Microbiology 70, no 1 (janvier 2004) : 174–81. http://dx.doi.org/10.1128/aem.70.1.174-181.2004.

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ABSTRACT The purpose of this investigation was to examine the capacity of the biphenyl catabolic enzymes of Comamonas testosteroni B-356 to metabolize dihydroxybiphenyls symmetrically substituted on both rings. Data show that 3,3′-dihydroxybiphenyl is by far the preferred substrate for strain B-356. However, the dihydrodiol metabolite is very unstable and readily tautomerizes to a dead-end metabolite or is dehydroxylated by elimination of water. The tautomerization route is the most prominent. Thus, a very small fraction of the substrate is converted to other hydroxylated and acidic metabolites. Although 2,2′-dihydroxybiphenyl is a poor substrate for strain B-356 biphenyl dioxygenase, metabolites were produced by the biphenyl catabolic enzymes, leading to production of 2-hydroxybenzoic acid. Data show that the major route of metabolism involves, as a first step, a direct dehydroxylation of one of the ortho-substituted carbons to yield 2,3,2′-trihydroxybiphenyl. However, other metabolites resulting from hydroxylation of carbons 5 and 6 of 2,2′-dihydroxybiphenyl were also produced, leading to dead-end metabolites.
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Borodina, Elena, Tim Nichol, Marc G. Dumont, Thomas J. Smith et J. Colin Murrell. « Mutagenesis of the “Leucine Gate” To Explore the Basis of Catalytic Versatility in Soluble Methane Monooxygenase ». Applied and Environmental Microbiology 73, no 20 (17 août 2007) : 6460–67. http://dx.doi.org/10.1128/aem.00823-07.

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ABSTRACT Soluble methane monooxygenase (sMMO) from methane-oxidizing bacteria is a multicomponent nonheme oxygenase that naturally oxidizes methane to methanol and can also cooxidize a wide range of adventitious substrates, including mono- and diaromatic hydrocarbons. Leucine 110, at the mouth of the active site in the α subunit of the hydroxylase component of sMMO, has been suggested to act as a gate to control the access of substrates to the active site. Previous crystallography of the wild-type sMMO has indicated at least two conformations of the enzyme that have the “leucine gate” open to different extents, and mutagenesis of homologous enzymes has indicated a role for this residue in the control of substrate range and regioselectivity with aromatic substrates. By further refinement of the system for homologous expression of sMMO that we developed previously, we have been able to prepare a range of site-directed mutations at position 110 in the α subunit of sMMO. All the mutants (with Gly, Cys, Arg, and Tyr, respectively, at this position) showed relaxations of regioselectivity compared to the wild type with monoaromatic substrates and biphenyl, including the appearance of new products arising from hydroxylation at the 2- and 3- positions on the benzene ring. Mutants with the larger Arg and Trp residues at position 110 also showed shifts in regioselectivity during naphthalene hydroxylation from the 2- to the 1- position. No evidence that mutagenesis of Leu 110 could allow very large substrates to enter the active site was found, however, since the mutants (like the wild type) were inactive toward the triaromatic hydrocarbons anthracene and phenanthrene. Thus, our results indicate that the “leucine gate” in sMMO is more important in controlling the precision of regioselectivity than the sizes of substrates that can enter the active site.
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Yam, Katherine C., Sachi Okamoto, Joseph N. Roberts et Lindsay D. Eltis. « Adventures inRhodococcus — from steroids to explosivesThis article is based on a presentation by Dr. Lindsay Eltis at the 60th Annual Meeting of the Canadian Society of Microbiologists in Hamilton, Ontario, 14 June 2010. Dr. Eltis was the recipient of the 2010 Norgen Biotek Corporation / CSM Award, an annual award sponsored by Norgen Biotek and the Canadian Society of Microbiologists intended to recognize outstanding scientific work in microbiology by a Canadian researcher. » Canadian Journal of Microbiology 57, no 3 (mars 2011) : 155–68. http://dx.doi.org/10.1139/w10-115.

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Rhodococcus is a genus of mycolic-acid-containing actinomycetes that utilize a remarkable variety of organic compounds as growth substrates. This degradation helps maintain the global carbon cycle and has increasing applications ranging from the biodegradation of pollutants to the biocatalytic production of drugs and hormones. We have been using Rhodococcus jostii RHA1 as a model organism to understand the catabolic versatility of Rhodococcus and related bacteria. Our approach is exemplified by the discovery of a cluster of genes specifying the catabolism of cholesterol. This degradation proceeds via β-oxidative degradation of the side chain and O2-dependent cleavage of steroid ring A in a process similar to bacterial degradation of aromatic compounds. The pathway is widespread in Actinobacteria and is critical to the pathogenesis of Mycobacterium tuberculosis , arguably the world’s most successful pathogen. The close similarity of some of these enzymes with biphenyl- and polychlorinated-biphenyl-degrading enzymes that we have characterized is facilitating inhibitor design. Our studies in RHA1 have also provided important insights into a number of novel metalloenzymes and their biosynthesis, such as acetonitrile hydratase (ANHase), a cobalt-containing enzyme with no significant sequence identity with characterized nitrile hydratases. Molecular genetic and biochemical studies have identified AnhE as a dimeric metallochaperone that delivers cobalt to ANHase, enabling its maturation in vivo. Other metalloenzymes we are characterizing include N-acetylmuramic acid hydroxylase, which catalyzes an unusual hydroxylation of the rhodococcal and mycobacterial peptidoglycan, and 2 RHA1 dye-decolorizing peroxidases. Using molecular genetic and biochemical approaches, we have demonstrated that one of these enzymes is involved in the degradation of lignin. Overall, our studies are providing fundamental insights into a range of catabolic processes that have a wide variety of applications.
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Desaulniers, Daniel, K. Leingartner, G. Pelletier, G. H. Xiao et W. J. Bowers. « Effects of Developmental Exposure to Mixtures of Environmental Contaminants on the Hepatic Metabolism of Estradiol-17β in Immature Female Sprague Dawley Rats ». International Journal of Toxicology 31, no 5 (22 août 2012) : 454–66. http://dx.doi.org/10.1177/1091581812457431.

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Exposure to environmental contaminants induces the activation of cytochrome P450s (CYP) which lead to the hydroxylation of contaminants and endogenous hormones such as estrogens. The hydroxylation of estrogens forms catecholestrogens (CEs), one of them being the mutagenic 4-hydroxyestradiol-17β (4−OH−E2). Catecholestrogens are transformed by catechol -o-methyltransferases (COMTs) into nonreactive methoxyestrogens. To investigate the hepatic metabolism of estradiol-17β in female offspring at postnatal day (PND) 21, pregnant rats were dosed daily from gestation day 1 until PND 21 with 2 dose levels of organochlorine pesticides (OCPs; 0.019 or 1.9 mg/kg per d), methylmercury (MeHg; 0.02 or 2 mg/kg per d), polychlorinated biphenyls (PCBs; 0.011 or 1.1 mg/kg per d), or a mixture (M; 0.05 or 5 mg/kg per d) including all 3 groups of chemicals. Concentrations of organochlorines in the mixture M were based on their proportions in serum of the Canadian Arctic population. The messenger RNA (mRNA) expressions of CYP and COMT were analyzed by quantitative reverse transcriptase–polymerase chain reaction (qRT-PCR). High-performance thin layer chromatography and phosphor imaging were used to measure the transformation of 14C substrates into estrogen metabolites. The low-dose treatments or the MeHg groups had no effect. The high-dose OCP, PCB, and M group increased the production of 2-OH-E2 and 6α-OH-E2, while only the PCB and M groups increased the 2-OH-CE/methoxyestrogen ratio. In all groups, the cytosolic COMT activity exceeded the microsomal production rate of 4-OH-E2. Although the M treatment included the PCB and OCP mixtures, it did not modify the estrogen metabolism more than did the PCB mixture alone. This endocrine disruption information contributes to our understanding of chemical interactions in the toxicology of chemical mixtures.
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Duan, Shitao, Yuanshuang Xu, Xinying Zhang et Xuesen Fan. « ChemInform Abstract : Synthesis of 2,2′-Biphenols Through Direct C(sp2)-H Hydroxylation of [1,1′-Biphenyl]-2-ols. » ChemInform 47, no 52 (décembre 2016). http://dx.doi.org/10.1002/chin.201652125.

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