• Bulletin of the Korean Chemical Society
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• v.26 no.2
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• pp.340-342
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• 2005

• Environmental Mutagens and Carcinogens
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• v.17 no.2
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• pp.97-108
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• 1997

The drugs or xenobiotics introduced to the body, are detoxified through the process of biotransformation in the body. In this process, most of the insoluble compounds become more polar, soluble and easily excretable. But, parts of introduced materials are metabolized to highly reactive electrophilic carcinogens through activation pathways. These metabolites are toxic and can react with DNA, RNA and proteins which are nucleophilic compounds. The objective of this study is to illustrate the aleactivation pathways of two highly reactive epoxide compounds, vinyl carbamate epoxide (VCO) and 2'-(4-nitrophenoxy)oxirane (NPO). They are the ultimate electrophilic carcinogens of ethyl carbamate(urethane) and 4-nitrophenyl vinyl ether, respectively. In this research, we studied the inhibition of the mutagenic activities of VCO or NPO by nuchieophiles [glutahione(GSH) and N-acetylcysteine(NAC)], detoxifying enzymes[epoxide hydrolase and glutathione-S-transferase(GST)] and intracellular organelles (microsomes and cytosol). In addition we also tested the suppression of DNA adducts formation by GSH and NAC. The results are summerized as follow. 1. The microsomes and cytosol which contain epoxide hydrolase and GST, respectively, decreased the mutagenicity of VCO (74% and 95%, respecfivel), and NPO (35% and 93%, respectively). The nucleophilic GSH and NAC decreased the mutagenicity by 86% (VCO) and 80% (NPO), 76% (VCO) and 40% (NPO), respectively. 2. The purified epoxide hydrolase decreased the mutagenicity of two epoxides in a dose-dependent manner, and GSH also decreased the mutagenicity in the presence of GST. 3. Formation of two DNA adducts, 7-(2'-oxoethyi)guanine (OEG) and N2,3-ethenoguanine(EG), were compared in the presence of calf thymus DNA and epoxide (VCO or NPO) in vitro system. The amounts of DNA adducts were decreased in the presence of GSH (25% and 29% in VCO, 32% and 29% in NPO), and NAC (14% and 16% in VCO, 21% and 11% in NPO), respectively. From these results, it is concluded that the ultimate carcinogenic metabolites, VCO and NPO, can be made in the body, but much of them may be inactivated and detoxified by the nucleophilic GSH, NAC and detoxifying enzymes (epoxide hydrolase and GST). Therefore, by these mechanism, the formation of DNA adducts and mutagenic activities of these two epoxides may be lowered in vivo.

• Archives of Pharmacal Research
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• v.22 no.5
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• pp.502-506
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• 1999

Different 2-(8,12 dimethyl-5-oxa-7(E), 11-tridecadienyl)-alkyl phenyl ethers, their mono oxirane and thirane derivatives were synthesized and tested on Culex pipiens quinquefasciatus Say for their juvenile hormone activity.

• Archives of Pharmacal Research
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• v.22 no.4
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• pp.398-400
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• 1999

Sufentanil, a potent anilidopiperidine analgesic, was synthesized from a simple thiophenylethylamine via six sequence. The key parts of this synthesis involved an efficient construction of thiophenylethylpiperidone by aminomethano desilylation-cyclization followed by Swern oxidation and a direct regioselective N-nucleophilic spiral epoxide cleavage with aniline promoted by Lewis acids.

• KSBB Journal
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• v.16 no.6
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• pp.562-567
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• 2001

Aspergillus niger LK harboring the enantioselective epoxide hydrolase (EHase) activity was isolated, and enantioselectivity of EHase was tested for various racemic aromatic epoxides. The gene encoding epoxide hydrolase was cloned from cDNA library generated by reverse transcriptase-polymerase chain reaction of the isolated total mRNA. Sequence analysis showed that the cloned gene encodes 398 amino acids with a deduced molecular mass of 44.5 kDa. Database comparison of the amino acid sequence reveals that it is similar to fungal EHase, whereas the sequence identity with bacterial EHase is very low. Recombinant expression of the cloned EHase in Escherichia coli BL21 yielded an active EHases, which can offer a potential biocatalyst for the production of chiral epoxides.

• Bulletin of the Korean Chemical Society
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• v.27 no.10
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• pp.1542-1548
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• 2006

Maleimide modified epoxy compounds were prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with diglycidylether of bisphenol-A. Triphenylphosphine was used as catalyst and methylethylketone as solvent. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of the maleimide epoxy compound with amine curing agents such as 1-(2-aminoethyl) piperazine (AEP) and 5-amino-1,3,3-trimethylcyclohexane methylamine isophorone diamine, IPDA) were studied. Incorporation of maleimide groups in the epoxy resin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples were found to have good thermal stability, chemical resistance (acid/alkali/solvent) and water absorption resistance.

• Journal of Life Science
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• v.12 no.6
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• pp.765-768
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• 2002

Enantioselective hydrolysis of racemic styrene oxide by Rhodotorula sp. CL-82 was investigated. Reaction conditions including pH, temperature, and volume ratio of organic cosolvent were optimized using response surface methodology, and the optimal conditions of pH, temperature, and the volume ratio of cosolvent were determined to be 7.64, $33.26^{\circ}C$, and 3.09 %(v/v), respectively. Chiral (S)-phenyl oxirane could be obtained with high enantiomeric purity (ee ＞ 99%) and 20% yield (theoretical yield ＝ 50%) at the optimal rendition.

• Bulletin of the Korean Chemical Society
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• v.31 no.8
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• pp.2272-2278
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• 2010

A new hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) is prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with Epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possesses both the oxirane ring and maleimide group. The curing reaction of these maleimidophenyl glycidylether epoxy compound (N-MPGE) with amines as curing agents such as ethylendiamine (EDA), diethylentriamine (DETA) and triethylenetetramine (TETA), aminoethylpiperazine (AEP) and isophoronediamine, IPDA), are studied. Incorporation of maleimide groups in the epichlorohydrin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples exhibited good thermal stability, excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.

• Macromolecular Research
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• v.13 no.3
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• pp.223-228
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• 2005

In the present work, a low-density polyethylene (LDPE) composite, filled with Zn-ion coated structural silica encapsulated with the diglycidyl ether of bisphenol-A (DGEBA), was synthesized using the conventional melt-blending technique in a sigma internal mixer. The catalytic activity of the Zn-ions (originating from the structural silica) towards the oxirane group (diglycidyl ether of bisphenol-A (DGEBA): encapsulating agent) was assessed by infrared spectroscopy. Two composites, each with a filler content of $2.5 wt\%$ were developed. The first one was obtained by melt blending the Zn-ion coated structural silica with LDPE in a co-rotating sigma internal mixer. The second one was obtained by melt blending the same LDPE, but with DGEBA encapsulated Zn-ion coated structural silica. Epoxy resin encapsulation of the Zn-ion coated structural silica resulted in its having good interfacial adhesion and a homogeneous dispersion in the polymer matrix. Furthermore, the encapsulation of epoxy resin over the Zn-ion coated structural silica showed improvements in both the mechanical and thermal properties, viz. a $33\%$ increase in the elastic modulus and a rise in the onset degradation temperature from 355 to $371^{\circ}C$, in comparison to the Zn-ion coated structural silica.

• Korean Journal of Microbiology
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• v.54 no.2
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• pp.136-139
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• 2018

The inhibitory compound (Compound S) against Ralstonia solanacearum and its conversion product (Compound S') were isolated from the culture filtrate of Bacillus subtilis JW-1 using a series of chromatography procedures. The structures were elucidated as alanyl-L-${\beta}$-(2,3-epoxycyclohexyl-4-one)alanine and alanyl-L-${\beta}$-(2,3-dihydroxycyclohexyl-4-one)alanine, respectively on the basis of nuclear magnetic resonance spectral data, including $^1H$, $^{13}C$, $^1H-^1H$ correlation spectroscopy and heteronuclear multiple bond correlation spectroscopy. The compound S exhibited a broad antimicrobial activity against $G^+$, $G^-$ bacteria, Saccharomyces cerevisiae and Candida albicans. The activity loss of the conversion product revealed that the epoxy function was essential for activity of Compound S.