• Journal of Life Science
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• v.12 no.4
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• pp.423-426
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• 2002

Enantioselective resolution of racemic para-nitrostyrene oxide was investigated using epoxide hydrolase activity of Aspergillus niger LK for the production of optically pure (S)-para-nitrostyrene oxide. To overcome the poor solubility of the substrate, enantioselective hydrolysis in an organic solvent was attempted under optimized reaction conditions including reaction temperature and water content. (S)-para-Nitrostyrene oxide with high optical purity (> 99% ee) was obtained at 37% yield using fungal epoxide hydrolase-catalyzed enantioselective resolution.

• Journal of Life Science
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• v.13 no.6
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• pp.788-793
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• 2003

Production of chiral phenyl oxirane by Rhodosporidium toruloides SJ-4 was investigated. Racemic phenyl oxirane was kinetically resolved by enantioselective hydrolysis reaction by epoxide hydrolase of R. toruloides in two-phase hollow-fiber reactor system. Dodecane with high concentration of the racemic substrate passed through the lumen side and cell suspension was recirculated through the shell side of the hollow fiber reactor For the removal of phenyl-1, 2-ethandiol to reduce the product inhibition to biocatalysts, another hollow-fiber reactor was employed to extract the diol. Racemic phenyl oxirane up to 300 mM was enantioselectively resolved with high enantiopurity (>99% ee) in hollow-fiber reactor system.

• Applied Chemistry for Engineering
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• v.25 no.5
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• pp.503-509
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• 2014

The carbon/porous silica composite membrane was fabricated in a simple manner, which could be successfully for the simultaneous separation and production of chiral epoxides and 1,2-diols, based on their differences in hydrophilic/hydrophobic natures. The chiral Co(III)-$BF_3$ salen catalyst adopted in the membrane reactor system has given the very high enantioselectivity and recyclability in hydrolysis of terminal epoxides such as ECH, 1,2-EB, and SO. The optically pure epoxide and the chiral catalyst were collected in the organic phase after hydrolysis reaction. The hydrophilic water-soluble 1,2-diol product hydrolyzed by chiral salen diffused into the aqueous phase through the SBA-16 or NaY/SBA-16 silica composite layer during the reaction. The water acted simultaneously as a reactant and a solvent in the membrane system. One optical isomer was obtained with high purity and yield, and furthermore the catalysts could be recycled without observable loss in their activity in the continuous flow-type membrane reactor.

• Applied Chemistry for Engineering
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• v.18 no.3
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• pp.279-283
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• 2007

Epoxide hydrolase (EH) gene of Caulobacter crescentus was cloned by PCR and expressed in Escherichia coli. The C. crescentus EH (CcEH) primarily attacked at the benzylic carbon of (S)-styrene oxide, while the CcEH preferentially attacked at the terminal carbon of (R)-styrene oxide, thus leading to the formation of (R)-phenyl-1,2-ethanediol as the main product. (R)-phenyl-1,2-ethanediol was obtained with 85% enantiomeric excess and yield of 69% from racemic styrene oxide via enantioconvergent hydrolysis by using recombinant CcEH as the single biocatalyst.

• Applied Chemistry for Engineering
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• v.26 no.2
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• pp.132-137
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• 2015

BEA-zeolite was modified by alkaline solution to introduce mesoporosity in the crystals and the homogeneous chiral Co(III) salen was immobilized in the mesopores. The dinuclear chiral Co(salen)-$GaCl_3$ catalyst immobilized on mesoporous BEA-zeolite showed high activity for the regioselective ring opening of terminal epoxides by carboxylic acids. Various chiral monoester derivatives could be synthesized with moderate enantioselectivity (47~69 ee%) from racemic epoxides through above reaction. When the chiral (S)-ECH was used as a reactant, it was efficiently resolved by carboxylic acid with a high enantioselectivity in the presence of heterogenized chiral salen catalyst, and the ring opened product afforded optically pure monoester epoxide (R)-GB (up to 98 ee%) through the ring closing in the basic solution by elimination of HCl. The heterogeneous catalyst could be fabricated easily, and the catalytic activity was retained for several times reuse without any further regeneration step.

• 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.

• Korean Journal of Environmental Agriculture
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• v.31 no.3
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• pp.255-263
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• 2012

BACKGROUND: The analysis for the concentration and enantiomeric ratio of OCPs have been performed to confirm the distribution and to emonstrate the pollution characteristics of chiral OCPs in ambient air. METHODS AND RESULTS: In ambient air at coastal and inland sites, concentrations and enantiomer fractions (EFs) of heptachlor (HEPT), eptachlor epoxide (HEPX), trans-chlordane (TC), cis-chlordane (CC), xychlordane (OXY), 2,4'-DDT, 2,4'-DDD with HRGC/HRMS were investigated to understand source and distribution of chiral organochlorine pesticides (OCPs) in ambient air. The mean concentrations of OCPs in ambient air were at the range of 0.027(heptachlor)~1.279 (4,4'-DDT) pg/m3 and 0.0005 (heptachlor)~0.1043 ng/g d.w. (TC), respectively. The mean EFs of OCPs in ambient air were at the range of 0.73 (HEPX)~0.45 (CC). Both preferential depletions of (+) and (-) enantiomer were observed for CC, indicated by EFs either <0.5 or >0.5, while preferential depletions of (-) enantiomer which mean EFs <0.5 were observed for chiral OCPs except TC and MC-5. CONCLUSION: OCPs in ambient air have been distributed from soil, but some of them such as chlordane, DDT etc. might have been introduced by long-range atmospheric transport, considering EFs by chiral analysis and trajectory analysis.

• Applied Chemistry for Engineering
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• v.18 no.4
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• pp.330-336
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• 2007

In this study, new dinuclear chiral Co (salen) complexes bearing $BF_3$ have been synthesized and their properties as the asymmetric catalyst have been examined. The NMR, UV and ESCA analyses were performed to determine the structure of synthesized catalysts. Their catalytic activity and selectivity have been demonstrated for the asymmetric ring opening of various terminal epoxides by hydrolytic kinetic resolution technology. The easily prepared dimeric complexes exhibited very high enantioselectivity for the asymmetric ring opening of epoxides with $H_2O$ nucleophile, providing enantiomerically enriched terminal epoxides (> 99 %ee). The dimeric structured chiral salen showed remakablely enhanced reactivity and may be employed substantially lower loadings than its monomeric analogues, and in addition no racemization happened during the separation of product epoxides. The system described in this work is very efficient for the sinthesis of chiral epoxide and 1,2-diol intermediates.

• Journal of Life Science
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• v.13 no.6
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• pp.794-798
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• 2003

Batch production of (S)-phenyl oxirane was investigated using epoxide hydrolase activity of Rhodosporidium toruloides SJ-4. Effect of reaction condition of asymmetric biohydrolysis of racemic phenyl oxirane was analyzed and optimized by response surface methodology. The optimal conditions of pH, temperature and DMSO cosolvent ratio were 7.4, $34^P\circ}C$, and 2.3%(v/v), respectively. The final yield was enhanced up to 67%, and reaction times required to reach 99% ee (enatiomeric excess) decreased down to 50% by response surface methodology Enantiopure (S)-phenyl oxirane with 100% enantiopurity and 24% yield (theoretical yield = 50%) was obtained from racemic substrate.

• Bulletin of the Korean Chemical Society
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• v.32 no.spc8
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• pp.2965-2969
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• 2011

Highly efficient and rapid aminolysis of epoxides with various amines in water under microwave irradiation in the absence of catalyst was developed. Chiral ${\beta}$-amino alcohols were formed in a short time with excellent yields.