• Biotechnology and Bioprocess Engineering:BBE
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• v.11 no.4
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• pp.282-287
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• 2006

A Caulobacter crescentus epoxide hydrolase(CCEH) from a recombinant Escherichia coli was purified to homogeneity using a three-step procedure. The CCEH protein was purified 7.3-fold with a 22.9% yield in overalll activity. The optimal reaction temperature and pH were determined to be $37^{\circ}C$ and pH 8.0, respectively. The addition of 10%(v/v) dimethylsulfoxide as a cosolvent improved the enantioselectivity of CCEH for a batch kinetic resolution of racemic indene oxide.

• KSBB Journal
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• v.16 no.3
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• pp.259-263
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• 2001

The development of hollow fiber reactor system for the production of chiral 1,2-epoxy-7-octence by epoxide hydrolase for Rhodotorula glutinis was investigated. Dodecane with high solubility of the racemic substrate passed through the lumen side of the hollow fiber reactor and cell suspension was recirculated through the shell side. The 2nd hollow fiber reactor was coupled to the production reactor to extract the diol byproduct which was the inhibitor of epoxide hydrolase. Optically pure (S)-1,2-epoxy-7-octene (0.6 M in dodecane) could be obtained using hollow-fiber reactor system.

• The Korean Journal of Pharmacology
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• v.21 no.1
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• pp.1-11
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• 1985

The effects of feeding indole, indole-3-carbinol and benzofuran (all at 5 mmole/kg body wt./day) on various hepatic microsomal and cytosolic enzyme activities involved in xenobiotic metabolism have been compared. Benzofuran was found to elevate the activities of many enzymes both in microsomes (e.g., aniline hydroxylase, 7-ethoxycoumarin O-deethylase, p-nitrophenol UDPGA-transferase and epoxide hydrolase) and in cytosol (e.g., glutathione reductase, glutathione S-transferase, NADH:quinone reductase and UDP-glucose dehydrogenase). The structures of indole and indole-3-carbinol are similar to benzofuran except for the substitution of nitrogen with oxygen atom within the furan ring. Results showed that the activities of UDPGA-transferase and NADH:quinone reductase were not elevated by these indole compounds. While the chemical structure of these two indole compounds are identical except for the presence of the carbinol (methanol) group in indole-3-carbinol, there were marked differences in the types and activities of microsomal enzymes that were enhanced. Among the microsomal enzyme activities determined, indole elevated only the NADPH:cytochrome c reductase, while indole-3-carbinol increased several mixed function oxidase and particularly the epoxide hydrolase activities. Based on the chemical structures of tested compounds and the observed results, possible explanations for the mechanisms involved in elevating epoxide hydrolase activity by benzofuran and indole-3-carbinol are discussed.

• Bulletin of the Korean Chemical Society
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• v.33 no.7
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• pp.2213-2218
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• 2012

Efficient synthetic routes were developed to prepare a sizable amount (4-15 grams) of the chiral epoxides 4-6 as versatile intermediates for the synthesis of aspartyl protease inhibitors of therapeutic interest such as HIV protease and ${\beta}$-secretase. Oxidative cleavage of the C(2)-C(3) double bond of L-ascorbic acid followed by functional group manipulation led to the preparation of the epoxide 10, which was opened with an azide to yield a common aziridine intermediate 12. Through opening of the aziridine ring of 12 with either a carbon or a sulfur nucleophile, chiral epoxide precursors 4-6 could be prepared for various HIV protease inhibitors. Except for the final low melting epoxides 5 and 6, all intermediates were obtained as crystalline solids, thus the synthetic pathway can be easily applied to a large-scale synthesis of the chiral epoxides.

• Food Science of Animal Resources
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• v.22 no.2
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• pp.137-144
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• 2002

Pork loins that retailed in market were used as experimental samples. Some pork samples in raw state were packaged with PVDC in either aerobic or vacuum condition. The other pork samples were cooked until core temperature reached at 70$\^{C}$ and then packaged immediately in the same way with the raw samples. After these samples were irradiated by electron beam 6 kGy, the samples were stored in a refrigerator (2∼4$\^{C}$). Identification and quantification of cholesterol oxides were performed at 0 and 7 days. The results were following. During the early stage of storage, cholesterol oxides were not produced from the raw meat samples, but with the passage of storage time,7 $\alpha$-hydroxycholesterol, 7$\beta$-hydroxycholesterol, 7-ketocholesterol, 20 $\alpha$-hydroxycholesterol, $\beta$-epoxide and $\alpha$-epoxide, which were not produced during the early stage of storage, were produced. The production of cholesterol and lipid oxidation products were significantly higher (P<0.05) in the meats with aerobic packaging than those with vacuum packaging, Cooked meat after irradiation showed 7 $\alpha$-hydroxycholesterol, 7 $\beta$-hydroxycholesterol, $\alpha$-epoxide and cholestanetriol on the 7th day of storage, although those chemicals were not produced during the early stage of storage. Production of cholesterol oxides was significantly increased (P<0.05) with the passage of storage time for all treatments, and showed significantly lower value (P<0.05) with the vacuum packaging than these for aerobic packaging. Species of cholesterol oxides from irradiated meat after cooking were similar to those from cooked meat after irradiation. Collectively, it was found that the production of cholesterol oxides was more easily affected by packaging condition than irradiation.

• Journal of Animal Science and Technology
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• v.44 no.1
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• pp.113-122
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• 2002

Beef loins that retailed in market were used as experimental samples. Some beef samples in raw state were packaged with PVDC as aerobic and vacuum condition. The other beef samples were cooked until core temperature arrived at 70$^{\circ}C$ and then packaged immediately in the same way of raw samples. After these samples were irradiated by electron beam 6kGy, irradiated samples were stored in refrigerator(2～4$^{\circ}C$). Identify and quantity of cholesterol oxides were analysed stored at 0 and 7 days, respectively. During the early stage of storage, 7$\beta$-hydroxycholesterol and 7-ketocholesterol were respectively produced from the raw meat samples, and the production of these chemicals were significantly higher (P$<$0.05) from the meats with aerobic packaging than those with vacuum packaging. With the passage of storage time, 7$\alpha$-hydroxycholesterol, 20$\alpha$-hydroxycholesterol, $\beta$-epoxide, $\beta$-epoxide and some other chemicals, which were not produced during the early stage of storage, were produced, Also, the production of these chemicals were significantly increased (P$<$0.05) with the passage of storage time. Cooked meat after irradiation and irradiated meat after cooking produced cholesterol on the 7th day of storage, although this chemical was not produced during the early stage of storage. Production of cholesterol oxides was significantly increased (P$<$0.05) with the passage of storage time for all treatments, and showed significantly lower value (P$<$0.05) with the vacuum packaging than aerobic packaging. Summarizing the aforementioned results, it was found that the production of cholesterol oxides was more easily affected by packaging condition than irradiation.

• Bulletin of the Korean Chemical Society
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• v.31 no.9
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• pp.2514-2518
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• 2010

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

• 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.

• Natural Product Sciences
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• v.21 no.1
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• pp.25-29
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• 2015

In a continuation of our studies to discover bioactive secondary metabolites from marine sources, we further investigated samples from a tryptamine and phenyl-alkane producing sponge, which resulted in the isolation of four uncommon small molecules and five nucleosides. Their structures were determined to be 7,8-dihydroimidazo[1,5-c]pyrimidin-5(6H)-one (1), 5-chlorocavernicolin (2), maleimide-5-oxime (3), 3-methylmaleimide-5-oxime (4), uridine (5), 2'-deoxyuridine (6), thymidine (7), adenine (8), and adenosine (9) by spectroscopic analyses. The isolated compounds were evaluated for inhibitory activity against soluble epoxide hydrolase (sEH) as well as the Wnt/${\beta}$-catenine signaling pathway.

• Korean Journal of Environmental Agriculture
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• v.20 no.2
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• pp.79-85
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• 2001

From July to November 1999, air samples were collected from Ansung, Korea, to identify the seasonal variation in organochlorine pesticides(OCPs). OCPs maximum(mean) concentrations were as follows: heptachlor, $14.0\;pg/m^3(3.6\;pg/m^3)$; heptachlor epoxide, $28.7\;pg/m^3(11.7\;pg/m^3)$; DDE, $40.6\;pg/m^3(20.6\;pg/m^3)$; endosulfan sulfate, $98.9\;pg/m^3(36.6\;pg/m^3)$. The higher concentration of the locally and seasonally used pesticide endosulfan[1759.2 $pg/m^3(453.4\;pg/m^3)$] was found. The concentrations of all OCPs were higher in summer than those in fall. This pattern suggests that the concentrations may be increased by evaporation from surfaces(soil, water, vegetation, etc) with increasing the temperature and by much usage in growing season, particularly in summer, for endosulfan.