• Title/Summary/Keyword: Aromatic ring cleavage

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Syntheses of New Film-Forming Aromatic Poly(amide-imide)s Containing Isoindoloquinazolinedione Unit in the Backbone: Poly(biphenylphthalicdianhydride-oxydianiline-4,4-diamino-3-carbamoyl-benzanilide) (Poly(BPDA-ODA-DACB))

  • Kang, Seog-Joo;Hong, Sung-Il;Park, Chong-Rae;Oh, Tae-Jin
    • Fibers and Polymers
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    • v.2 no.2
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    • pp.92-97
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    • 2001
  • New film forming aromatic poly(amide-imide)s containing isoindoloquinazolinedione (IQ) unit in the backbone chain (polymer XIV) have been successfully synthesized by preparing prepolymers of poly(amic acid-carbonamide). followed by subsequent thermal cyclization of the prepolymers. 4,4-Diamino-3-carbamoylbenzanilide (DACB) V has been synthesized by reduction of 3-carbamoyl-4-amino-4-nitrobenzanilide IV. The prepolymers of poly(amic-acid-carbonamide) (polymers VII and VIII) which exhibit viscosities ranging from 1.4 to 1.7 dl/g have been prepared by a condensation polymerization of monomers such as BPDA, ODA, and DACB. Polymer XIV has been obtained by thermal cyclization of the polymers VII and VIII. During the thermal cyclization reaction, imide ring structure was first introduced and then transformed to the structure of IQ unit. The thermal degradation rate of the resultant polymers were influenced by the cleavage of amide bond but the final char yield was comparable to that of poly(BPDA-ODA).

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Comparative Genomic Analysis and BTEX Degradation Pathways of a Thermotolerant Cupriavidus cauae PHS1

  • Chandran Sathesh-Prabu;Jihoon Woo;Yuchan Kim;Suk Min Kim;Sun Bok Lee;Che Ok Jeon;Donghyuk Kim;Sung Kuk Lee
    • Journal of Microbiology and Biotechnology
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    • v.33 no.7
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    • pp.875-885
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    • 2023
  • Volatile organic compounds such as benzene, toluene, ethylbenzene, and isomers of xylenes (BTEX) constitute a group of monoaromatic compounds that are found in petroleum and have been classified as priority pollutants. In this study, based on its newly sequenced genome, we reclassified the previously identified BTEX-degrading thermotolerant strain Ralstonia sp. PHS1 as Cupriavidus cauae PHS1. Also presented are the complete genome sequence of C. cauae PHS1, its annotation, species delineation, and a comparative analysis of the BTEX-degrading gene cluster. Moreover, we cloned and characterized the BTEX-degrading pathway genes in C. cauae PHS1, the BTEX-degrading gene cluster of which consists of two monooxygenases and meta-cleavage genes. A genome-wide investigation of the PHS1 coding sequence and the experimentally confirmed regioselectivity of the toluene monooxygenases and catechol 2,3-dioxygenase allowed us to reconstruct the BTEX degradation pathway. The degradation of BTEX begins with aromatic ring hydroxylation, followed by ring cleavage, and eventually enters the core carbon metabolism. The information provided here on the genome and BTEX-degrading pathway of the thermotolerant strain C. cauae PHS1 could be useful in constructing an efficient production host.

(-)-β-Narcotine: A Facile Synthesis and the Degradation with Ethyl Choroformate

  • Lee, Dong-Ung
    • Bulletin of the Korean Chemical Society
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    • v.23 no.11
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    • pp.1548-1552
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    • 2002
  • $(-)-\beta-Narcotine$ (6), a phthalideisoquinoline alkaloid, was synthesized conveniently by the direct condensation of cotarnine (1) and iodomeconine (2) prepared by aromatic iodination using thallium trifluoroacetate/KI and by the successive reduction of resulting $iodo-{\beta}-narcotine$ (5) with aluminum amalgam. Its structure including a stereochemistry was confirmed by instrumental analyses. This synthetic alkaloid was degraded with ethyl chloroformate at room temperature to afford the chloro-carbamate 6b as a crystalline intermediate, which was unexpectedly converted into the carbinol 8 by exchange of Cl with OH of water contained in the solvents and the ethoxy-carbamate 9, probably because of ethanol added to chloroform as a solvent stabilizer during the purification by column chromatography.

Binding Mode Studies of Indenoisoquinoline Analogues into Human Topoisomerase I-DNA Complex Using Flexible Docking (Human Topoisomerase I-DNA 절개가능 복합체에 대한 Indenoisoquinoline 유도체들의 결합양상 연구)

  • Park, In-Seon;Kim, Bo-Yeon;Kim, Choon-Mi;Choi, Sun
    • YAKHAK HOEJI
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    • v.53 no.4
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    • pp.228-234
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    • 2009
  • Topoisomerase I (Topo I) participates in the DNA replication, transcription, and repair. Binding of Topo I inhibitor to the Topo I-DNA cleavage complex forms stabilized ternary complex which blocks DNA religation and ultimately causes cell death. Camptothecin (CPT) and its derivatives have been among the most effective anticancer drugs by inhibition of topo I. However, efforts to synthesize non-CPT drugs have been actively going on because the CPT derivatives have several limitations such as poor solubility, short half-life, and side effects. As an indenoisoquinoline, NSC314622 is not as potent as CPT, but its chemical stability and slower reversibility of the cleavage complex made it a good lead compound. Recently, a series of indenoisoquinoline analogues were synthesized with substituted dimethoxy or methylenedioxy on the aromatic ring and alkylamino on the lactam nitrogen. Some of them showed quite good Topo I inhibitory activity. Using the computer docking program, Surflex-Dock, indenoisoquinoline analogues were docked into the human Topo I-DNA cleavable complex. The docking results showed that the compounds with activity better than NSC314622 intercalated between the -1 and +1 base pairs at the cleavage site, but those with little or no activities did not appear to intercalate. These results could be useful to design new Topo I inhibitors improved than CPT.

Proteomic Analysis of Polycyclic Aromatic Hydrocarbons (PAHs) Degradation and Detoxification in Sphingobium chungbukense DJ77

  • Lee, Soo Youn;Sekhon, Simranjeet Singh;Ban, Yeon-Hee;Ahn, Ji-Young;Ko, Jung Ho;Lee, Lyon;Kim, Sang Yong;Kim, Young-Chang;Kim, Yang-Hoon
    • Journal of Microbiology and Biotechnology
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    • v.26 no.11
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    • pp.1943-1950
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    • 2016
  • Polycyclic aromatic hydrocarbons (PAHs) are commonly present xenobiotics in natural and contaminated soils. We studied three (phenanthrene, naphthalene, and biphenyl) xenobiotics, catabolism, and associated proteins in Sphingobium chungbukense DJ77 by two-dimensional gel electrophoresis (2-DE) analysis. Comparative analysis of the growth-dependent 2-DE results revealed that the intensity of 10 protein spots changed identically upon exposure to the three xenobiotics. Among the upregulated proteins, five protein spots, which were putative dehydrogenase, dioxygenase, and hydrolase and involved in the catabolic pathway of xenobiotic degradation, were induced. Identification of these major multifunctional proteins allowed us to map the multiple catabolic pathway for phenanthrene, naphthalene, and biphenyl degradation. A part of the initial diverse catabolism was converged into the catechol degradation branch. Detection of intermediates from 2,3-dihydroxy-biphenyl degradation to pyruvate and acetyl-CoA production by LC/MS analysis showed that ring-cleavage products of PAHs entered the tricarboxylic acid cycle, and were mineralized in S. chungbukense DJ77. These results suggest that S. chungbukense DJ77 completely degrades a broad range of PAHs via a multiple catabolic pathway.

Cloning and Expression of pcbC and pcbD Genes Responsible for 2,3-Dihydroxybiphenyl Degradation from Pseudomonas sp. P20

  • Nam, Jung-Hyun;Oh, Hee-Mock;Kim, Chi-Kyung
    • Journal of Microbiology and Biotechnology
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    • v.5 no.2
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    • pp.68-73
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    • 1995
  • Pseudomonas sp. P20 was shown to be capable of degrading biphenyl and 4-chlorobiphenyl (4CB) to produce the corresponding benzoic acids wnich were not further degraded. But the potential of the strain for biodegradation of 4CB was shown to be excellent. The pcbA, B, C and D genes responsible for the aromatic ring-cleavage of biphenyl and 4CB degradation were cloned from the chromosomal DNA of the strain. In this study, the pebC and D genes specifying degradation of 2, 3-dihydroxybiphenyl (2, 3-DHBP) produced from biphenyl by the pebAB-encoded enzymes were cloned by using pBluescript SK(+) as a vector. From the pCK102 (9.3 kb) containing pebC and D genes, pCK1022 inserted with a EcoRI-HindIII DNA fragment (4.1 kb) carrying pebC and D and a pCK1092 inserted with EcoRI-XbaI fragment (1.95 kb) carrying pebC were constructed. The expression of pcbC and D' in E. coli CK102 and pebC in E. coli CK1092 was examined by gas chromatography and UV-vis spectrophotometry. 2.3-dihydroxybiphenyl was readily degraded to produce meta-cleavage product (MCP) by E. coli CK102 after incubation for 10 min, and then only benzoic acid(BA) was detected in the 24-h old culture. The MCP was detected in E. coli CK1022 containing pebC and 0 genes (by the resting cells assay) for up to 3 h after incubation and then diminished completely in 8 h, whereas the MCP accumulated in the E. coli CK1092 culture even after 6 h of incubation. The 2, 3-DHBP dioxygenases (product of pebC gene) produced by E. coli CK1, CK102, CK1023, and CK1092 strains were measured by native PAGE analysis to be about 250 kDa in molecular weight, which were about same as those of Pseudomonas sp. DJ-12, P. pseudoa1caligenes KF707, and P. putida OU83.

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Characteristics of Polycyclic Aromatic Hydrocarbons Degradation by Stenotrophomonas maltophilia (Stenotrophomonas maltophilia에 의한 방향족 화합물의 분해특성)

  • Choi, Chang-Seok;Lee, Tae-Jin;Park, Jin-Hee;Kim, Young-Sik;Kim, Jin-Woo
    • Journal of the Korea Organic Resources Recycling Association
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    • v.11 no.4
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    • pp.130-137
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    • 2003
  • In this study, Isolation was attempted to acquire a phenol utilizing bacterium for PAH degradation and to investigate the characteristics of PAH degradation. The isolate was identified by BIOLOG test as Stenotrophomonas maltophilia. Lower first order reaction constant was detected in the presence of lower phenol concentration. The yield coefficient of phenol was 0.1447mg cell/mg phenol. In the presence of naphthalene and phenol, phenol degradation was favorable. The isolate was capable of utilize naphthalene and phenanthrene as growth substrate but PAH, containing over 4-ring structure such as pyrene, was not degradable. The possible phenanthrene degradation pathway would be the addition of two hydroxy group on C-1 and C-2 position, followed by ortho cleavage, and then decarboxylation.

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Biodegradation of Kraft Lignins by White-Rot Fungi(I) -Lignin from Pitch Pine- (백색부후균에 의한 크라프트 리그닌의 분해(I) -리기다소나무 리그닌-)

  • 김명길;안원영
    • Journal of Korea Foresty Energy
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    • v.17 no.1
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    • pp.56-70
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    • 1998
  • This study was carried out to investigate the structural characteristics of kraft lignin and the wood degrading characteristics, the productivity of ligninolytic enzymes and the enzymatic degradation of kraft lignin by white-rot fungi. To purify kraft lignin, precipitation of kraft pulping black liquors of pitch pine meal was done by titration with lN $H_{2}SO_{4}$ reaching to pH 2, and isolation of the precipitates done by centrifugation. The isolated precipitates from pitch pine were redissloved in lN NaOH, reprecipitated by titration with lN $H_{2}SO_{4}$, washed with deionized water, and kept ofr analysis after freeze drying. Fractionation of the precipitates in solution by successive extraction with $CH_{2}Cl_{2}$ and MeOH, and the fractionates were named SwKL, SwKL I, SwKL II, and SwKL III for pitch pine kraft lignin. The more molecular weights of kraft lignin increased, the less phenolic hydroxyl groups and the more aliphatic hydroxyl groups. Because as the molecular weights increased, the ratio of etherified guaiayl/syringyl(G/S ratio) and the percentage were increased. The spectra obtained by 13C NMR and FTIR assigned by comparing the chemical shifts of various signals with shifts of signals from autherized ones reported. The optimal growth temperature and pH of white-rot fungi in medium were $28^{\circ}C$ and 4.5-5.0, respectively. Especially, in temperature and pH range, and mycelial growth, the best white-rot fungus selected was Phanerochaete chrysosporium for biodegradation. For the degradation pathways, the ligninolytic fungus jcultivated with stationary culture using medium of 1% kraft lignin as a substrate for 3 weeks at $28^{\circ}C$. The weight loss of pitch pine kraft lignin was 15.8%. The degraded products extracted successively methoanol, 90% dioxane and diethyl ether. The ether solubles were analyzed by HPLC. Kraft lignin degradation was initiated in $\beta$-O-4 bonds of lignin by the laccase from Phanerochaete chrysosporium and the degraded compounds were produced from the cleavage of $C\alpha$-$C\beta$ linkages at the side chains by oxidation process. After $C\alpha$-$C\beta$ cleavage, $C\alpha$-Carbon was oxidized and changed into aldehyde and acidic compounds such as syringic acid, syringic aldehyde and vanilline. And the other compound as quinonemethide, coumarin, was analyzed. The structural characteristics of kraft lignin were composed of guaiacyl group substituted functional OHs, methoxyl, and carbonyl at C-3, -4, and -5 and these groups were combinated with $\alpha$ aryl ether, $\beta$ aryl ether and biphenyl. Kraft lignin degradation pathways by Phanerochaete chrysosporium were initially accomplished cleavage of $C\alpha$-$C\beta$ linkages and $C\alpha$ oxidation at the propyl side chains and finally cleavage of aromatic ring and oxidation of OHs.

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Microbial degradation and other methods for accelerated degradation the Herbicide Imazapyr (제초제 Imazapyr 의 미생물에 의한 분해 및 기타 방법에 의한 분해 촉진)

  • Lee, Jae-Koo;Kwon, Jeong-Wook
    • Korean Journal of Environmental Agriculture
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    • v.17 no.1
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    • pp.5-10
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    • 1998
  • The microbial degradation, photosensitizer-mediated photolysis, and bioceramic- accelerated degradation of the herbicide imazapyr were investigated using four types of soil. 1. Seven strains of microorganisms isolated from the soil A and the active sludge collected from the waste water disposal plant in CheongJu did not give any distinct degradation products in pure culture. When imazapyr (10ppm) was incubated for 14days with each of the 6strains of the known bacteria, they did not produce any noticeable products, either, suggesting that imazapyr was degraded very little by microorganisms in aqueous media. Meanwhile, when 50ppm of imazapyr was incubated in soil A and B for 6months, a degradation product of m/z 279 was detected. It turned out to be 2-[(1-carbamoyl-1,2-dimethylpropyl)carbamoyl]nicotinic acid, which was formed by the hydrolytic cleavage of the imidazolinone ring and by tautomerism. When imazapyr was exposed to sunlight, degradation rates were 14.6% under the control and 66.0, 76.5, 26.7, and 90.0% in the presence of PS-1 (100ppm), PS-1 (200ppm), PS-2(100ppm), and PS-3(100ppm), respectively, and a degradation product of m/z 149 was tentatively identified in the treatment of PS-1. 2. When soil C and D treated with bioceramic were incubated for 7weeks, the $^{14}C$-activities of $^{14}CO_2$ evolved were 2.03 and 1.12% of the originally applied ones, respectively, whereas those in control soils without bioceramic were 1.88 and 0.82% showing no significant defferences.After 5 weeks, however,the differences in the amounts of $^{14}CO_2$ between the two treatments increased gradually, suggesting the bioceramic effect.

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