• Title/Summary/Keyword: C-ring cleavage

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A Pathway for 4-Chlorobenzoate Degradation by Pseudomonas sp. S-47

  • Seo, Dong-In;Chae, Jong-Chan;Kim, Ki-Pil;Kim, Young-Soo;Lee, Ki-Sung;Kim, Chi-Kyung
    • Journal of Microbiology and Biotechnology
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    • v.8 no.1
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    • pp.96-100
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    • 1998
  • Pseudomonas sp. S-47 degraded 4-chlorobenzoate (4CBA) to 4-chlorocatechol (4CC) that was subsequently ring-cleaved to form 5-chloro-2-hydroxymuconic semialdehyde. These intermediate compounds were identified by GC-mass spectrometry and UV-visible spectrophotometry. 5-chloro-2-hydroxymuconic acid converted from 5-chloro-2- hydroxymuconic semialdehyde (5C-2HMS) was dechlorinated to produce 2-hydroxypenta-2,4-dienoic acid (2HP-2,4DA) by the strain. These results indicate that Pseudomonas sp. S-47 degrades 4CBA to 2HP-2,4DA via a novel pathway including the meta-cleavage of 4CC and dechlorination of 5C-2HMS.

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The Reaction between Organothioenamine Phosphonate and Styrene Oxide (유기 티오엔아민 포스포네이트와 산화스티렌과의 반응)

  • Keun Jae Kim;Chi Sun Han
    • Journal of the Korean Chemical Society
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    • v.20 no.4
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    • pp.295-298
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    • 1976
  • The fact that a reaction between organothioenamine phosphonate and styrene oxide produces a derivative of cyclopropane has been proved by structural identification. This suggests that an anionic oxygen atom from the ring opening of the styrene oxide by nucleophilic attack of thioenamine phosphonate links to the phosphorous atom to from a betaine as an intermediate which is followed by cleavage of the weak P-C bond. The dextrorotatory optical activity of the product showed that the reaction was under the control of steric stability of the benzyl carbon in styrene which leads to the product through a sterically stable pathway.

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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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Pyrolytic Behavior of $l$-Menthol ($l$-멘솔의 열분해 특성 분석)

  • 이창국;이재곤;장희진;이영택;곽재진
    • Journal of the Korean Society of Tobacco Science
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    • v.25 no.2
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    • pp.103-110
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    • 2003
  • This study was conducted to investigate the pyrolysis products of ι-menthol by Curie-Point pyrolysis. The pyrolysis of ι-menthol was performed at 16$0^{\circ}C$, 42$0^{\circ}C$, $650^{\circ}C$, and 92$0^{\circ}C$ by Curie-Point Pyrolyzer and their pyrolysis products were analyzed by GC/MSD. In addition, tobacco leaves added ι-menthol were pyrolyzed at the same condition in case of ι-menthol. The beginning temperature for pyrolysis formation was in the vicinity of 42$0^{\circ}C$ and the major components of the pyrolysis products identified were iso-menthol, 2-menthene, menthomenthene, and menthone. The amount of these components was increased by increasing temperature and the hydrocarbons such as hexadecene and pentadecene formed by ring cleavage were generated at 92$0^{\circ}C$. The yield of ι-menthol in pyrolysis of tobacco leaves was decreased as the temperature of pyrolysis was raised and the pyrolysis products of ι-menthol weren't identified in the pyrolysis of tobacco leaves. Also, to analyze the weight decrease, ι-menthol was analysed by thermal analyzer(TA), and then the weight decrease of ι-menthol was occurred in the vicinity of 18$0^{\circ}C$.

Induction by Carvone of the Polychlorinated Biphenyl (PCB)-Degradative Pathway in Alcaligenes eutrophus H850 and Its Molecular Monitoring

  • Park, Young-In;So, Jae-Seong;Koh, Sung-Cheol
    • Journal of Microbiology and Biotechnology
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    • v.9 no.6
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    • pp.804-810
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    • 1999
  • There is a possibility that carvone, a monoterpene from spearmint (Mentha spicata), could induce the bph degradative pathway and genes in Alcaligenes eutrophus H850, which is a known Gram-negative PCB degrader with a broad substrate specificity that was thoroughly investigated with Arthrobacter sp. BIB, a Gram-positive PCB degrader. The strains BIB and H850 were unable to utilize and grow on the plant terpene [(R)-(-)-carvone] (50ppm) to be recognized as a sole carbon source. Nevertheless, the carvone did induce 2,3-dihydroxybiphenyl 1,2-dioxygenase (encoded by bphC) in the strain B lB, as observed by a resting cell assay that monitors accumulation of a yellow meta ring fission product from 4,4'-dichlorobiphenyl (DCBp). The monoterpene, however, did not appear to induce the meta cleavage pathway in the strain H850. Instead, an assumption was made that the strain might be using an alternative pathway, probably the ortho-cleavage pathway. A reverse transcription (RT)-PCR system, utilizing primers designed from a conserved region of the bphC gene of Arthrobacter sp. M5, was employed to verify the occurrence of the alternative pathway. A successful amplification (182bp) of mRNA transcribed from the N-terminal region of the bphC gene was accomplished in H850 cells induced by carvone (50ppm) as well as in biphenyl-growth cells. It is, therefore, likely that H850 possesses a specific PCB degradation pathway and hence a different substrate specificity compared with B1B. This study will contribute to an elucidation of the dynamic aspects of PCB bioremediation in terms of roles played by PCB degraders and plant terpenes as natural inducer substrates that are ubiquitous and environmentally compatible.

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Molecular Cloning and Characterization of Catechol 2, 3-Dioxygenase Gene from Aniline-Degrading Psseudomonas acidovorans

  • Lee, Ji-Hyun;Bang, Sung-Ho;Park, Youn-Keun;Lee, Yung-Nok
    • Korean Journal of Microbiology
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    • v.30 no.4
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    • pp.316-321
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    • 1992
  • Catechol 2, 3-dioxygenase (C230) catalyses the oxidative ring cleavage of catechol to 2-hydroxymuconic semialdehyde. This is one of the key reactions in the metabolism of the widespresd pollutant aniline. We have cloned a gene encoding C230 from cells of the aniline degrading bacteria, Pseudomonas acidovorance KCTC2494 strain and expressed in E. coli, A 11.3-kilobase Sau3A partial digested DNA fragment from KCTC2494 was cloned into phagemid vector pBluescript and designated as pLP201. The C230 gene was mapped to a 2.8-kb region, and the derection of transcription was determined. The cloned C230 gene contains its own promoter which can be recognized and employed by E. coli transcriptional apparatus. C230 activities of subclones were identified by enzyme assay and activity staining. The T7 RNA promoter/polymerase system and maxicell analysis showed that a polypeptide with Mw of 35 kDa is the C230 gene product.

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Effective α-Helix Stabilization via Hexenyl Propionate Cross-Link

  • Yoo, Jiyeon;Kim, Young-Woo
    • Bulletin of the Korean Chemical Society
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    • v.35 no.12
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    • pp.3627-3631
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    • 2014
  • In this study we examined two ester-containing cross-links, hex-2-enyl acetate and hex-2-enyl propionate, as new cross-linking systems for helix stabilization of short peptides. We demonstrated that these hexenyl ester cross-links can be readily installed via a ruthenium-mediated ring-closing metathesis reaction of L-aspartic acid 4-allyl ester or L-glutamic acid 5-allyl ester at position i and (S)-2-(4'-pentenyl)alanine at position i+4 using second generation Hoveyda-Grubbs catalyst at $60^{\circ}C$. Between these two cross-links, we found that the hex-2-enyl propionate significantly stabilizes the ${\alpha}$-helical conformations of short model peptides. The helix-stabilizing effects of the hex-2-enyl propionate tether appear to be as powerful as Verdine's i,i+4 all-hydrocarbon stapling system, which is one of the most widely used and the most potent helix-stabilizing cross-linking systems. Furthermore, the hex-2-enyl propionate bridge is reasonably robust against non-enzymatic hydrolytic cleavage at a physiological pH. While extended studies for probing its chemical scopes and biological applications are needed, we believe that this new helix-stabilizing system could serve as a useful chemical tool for understanding protein folding and designing conformationally-constrained peptide drugs.

Anti-tumor effect of new compound, 127, through the induction of apoptosis (새로운 화합물 c-127의 세포고사 유도에 의한 항암효과)

  • Baek, Ki Hwan;Han, A Lum;Shin, Sae Ron;Jin, Chun Mae;Yoon, Young Wook;Yu, Seung Taek;Kim, Jong Duk;Choi, Du Young
    • Clinical and Experimental Pediatrics
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    • v.52 no.6
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    • pp.696-700
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    • 2009
  • Purpose : We screened more than 350 compounds with an endoperoxide ring structure in search of an anti-leukemic drug and found that compound 127 (c-127) could induce significant cytotoxicity in HL-60 cells. In this study, we investigated the molecular mechanisms of compound 127-induced antitumor activity on HL-60 cells. Methods : HL-60 cells were cultured in Rosewell Park Memorial Institute 1640 and cell viability was measured by MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide], a tetrazole assay. Apoptosis was assessed by a DNA fragmentation test. Apoptotic machineries were determined by Western blot analysis. Results : C-127 could induce a cytotoxic effect at 24 h and apoptosis at 6 h, which was demonstrated with MTT assay and DNA fragmentation test, respectively. The apoptotic effect of this drug was caused by the activation of the intracellular caspase-8,3 activation, the cleavage of pro-apoptotic Bid, and the increase of c-Jun expression accompanied with JNK (Jun N-terminal kinases) phosphorylation. On the contrary, it increased the expression of anti-apoptotic Bcl-2 levels, leading to the induction of the induction of anti-apoptotic effect. Taken together, the present study demonstrated that c-127 was a potent inducer of cytotoxicity on HL-60 cells through apoptotic mechanisms, which included the activation of caspase family, the regulation of Bcl-2 family, and the activation of JNK signaling pathway. Conclusion : Our results suggest that c-127 has a strong antitumor activity through the regulation of various apoptotic machineries on HL-60 cells. The compound may be utilized as an effective and potentially therapeutic drug in leukemia.

Sonochemical Reaction of Fullerene Oxides, [C70(O)n](n≥1) with Aromatic Amines (방향족 아민 화합물과 풀러렌 산화물의 [C70(O)n](n≥1)의 초음파 화학 반응)

  • Ko, Weon-Bae;Park, Byoung-Eun;Lee, Young-Min
    • Elastomers and Composites
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    • v.43 no.1
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    • pp.31-38
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    • 2008
  • Sonochemical reaction of fullerene oxides, $[C_{70}(O)_n](n\geq1)$ with several aromatic amines such as 4-nitroaniline, 3-nitroaniline, and 4-isopropylaniline, in the presence of $FeCl_3$ were investigated under ultrasonic irradiation. This method is applicable to a wide variety of aromatic amines especially ring deactivated, to afford the corresponding cleavage products under mild conditions. The aminated fullerenes were confirmed by MALDI-TOF-MS and UV-vis spectra.

Synthesis and E-Beam-Mediated Gas Phase Fragmentation of Thiol-Containing Furoxans for Nanopatterned Alkyne Formation on Gold Surface

  • Koo, Hyun-Seo;Park, Kyung-Moon;Hwang, Kwang-Jin
    • Bulletin of the Korean Chemical Society
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    • v.31 no.12
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    • pp.3583-3587
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    • 2010
  • Furoxanthiols PFT and BPFT possessing thiomethyl or thiobenzyl groups in the furoxan ring were designed and synthesized as potential light-sensitive alkyne precursors on a gold surface. The synthesis of thiofuroxans PFT and BPFT was performed from the corresponding halofuroxans 1b and 2c, respectively, by the substitution with potassium thioacetate in ethyl acetate/ethanol or DMF, followed by basic hydrolysis as the key reactions. Electron-beammediated fragmentation of furoxans 1c and 2d in a mass spectrometer afforded the corresponding aryl alkyne fragments, with the evolution of NO in high preference. In the cases of thiofuroxans PFT and BPFT, carbon-sulfur bond cleavage was observed as a representative fragmentation, producing M-SH and M-SAc peaks, which competed with the release of NO. In the fragmentation of mono-aryl furoxan 1c, the release of molecule of NO was predominately observed to produce an M-NO fragment as a base peak by the formation of trimembered thiiranium or azirine intermediate.