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

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

• Proceedings of the Korean Society of Applied Pharmacology
• /
• 1997.04a
• /
• pp.75-75
• /
• 1997

뛰어난 혈당강하작용을 가지고 있는 oxirane carboxilic acid의 analogue 합성과 관련하여 oxirane carboxilic acid의 기본골격을 용이하게 형성할 수 있고 동시에 다앙한 관능기를 갖는 side chain을 도입할 수 있는 방법을 개발함으로써 다양한 유도체들을 합성하는데 이용하고자 함. 방법 및 결과 $\alpha$,$\beta$-unsaturated ester로부터 dioxirane을 이용한 직접적인 epoxidation을 통해서 보통의 방법으로는 얻기 어려운 oxirane carboxilic acid의 ester를 높은 수율로 합성할 수 있는 방법이 개발되었으며 특히 분자내에 cpoxide 존재하에서도 Mitsnobu 방법을 이용한 O-alkylation에 의해 aryl ether 결합을 형성할 수 있는 방법이 개발되었으며 이들 방법을 이용하여 다양한 유도체들을 합성하였다.

• Journal of Life Science
• /
• v.13 no.1
• /
• pp.105-109
• /
• 2003

Epoxide hydrolase (EH) gene from Aspergillus niger #33 was cloned from cDNA library generated by reverse transcriptase-polymerase chain reaction (RT-PCR). The nucleotide sequence analysis revealed that the deduced amino acid sequence was almost similiar to that of A. niger LCP521 previously reported. The cloned EH gene was transformed into Saccharomyces cerevisiae and expressed by addition of galactose. The recombinant S. cerevisiae showed hydrolytic activity toward racemic phenyl oxirane substrate based on chiral GC analysis, and can be used as a potential biocatalyst for the preparation of chiral phenyl oxirane.

• Journal of the Korea Institute of Military Science and Technology
• /
• v.7 no.2 s.17
• /
• pp.109-117
• /
• 2004

We synthesized energetic prepolymer(2-nitrato ethyl oxirane, NEO) for plastic-bonded explosive and measured its thermodynamic parameters. 2-Nitrato ethyl oxirane(NEO) as a monomer was synthesized from 4-butene-ol, the first-step was preparation of 1-nitrate-3-butene and second-step was synthesized 2-nitrate-ethyl oxirane from 1nitrate-3-butene and then polymerized by cationic ring opening polymerization. The unreacted monomer concentration was measured by GC. The thermodynamic parameters were obtained from the ceiling temperature(Tc) values of 1 mole monomer at each reaction temperature. We varied feed rate of monomer, concentration of initiator and monomer to control molecular weight and polydispersity of perpolymer(NEO). Number average molecular weight(Mn), polydispersity(PD), and glass transition temperature(Tg), viscosity of prepolymer(NEO) were 2000, 1.07, $-55^{\circ}C$ and 300 poise respectively.

• Journal of the Korea Institute of Military Science and Technology
• /
• v.18 no.2
• /
• pp.131-138
• /
• 2015

Energetic monomers with new design concept were synthesized for energetic prepolymers. Novel energetic monomers consisted of ring-opening polymerizable oxirane and a molecular explosive moiety instead of small explosophores as energetic functional groups. According to the design concept, glycidyl dinitroazetidine (GDNAZ) and glycidyl nitroazetidinol(GNAZO) energetic monomers were synthesized, respectively, and characterized by NMR, EA and GC MS. Heat of formation and detonation performance were calculated by theoretical method to evaluate energy performance of these novel energetic monomers. The result revealed that GDANZ and GNAZO possessed high potential as new energetic monomers for synthesizing energetic prepolymers and binders in PBXs.

• Journal of the Korean Chemical Society
• /
• v.30 no.2
• /
• pp.248-258
• /
• 1986

The electronic structures and geometries of model substituted oxiranes, and carbonyl ylides containing cyano, methoxy and thiomethoxy substituents were investigated by MNDO-SCF-MO method. Stabilization and geometries caused by substituents, the ease of formation of carbonyl ylides from oxiranes and the reactivities of the cycloaddition of substituted carbonyl ylides were investigated.

• Journal of the Korean Chemical Society
• /
• v.55 no.6
• /
• pp.1012-1017
• /
• 2011

Novel surfactants have been synthesized by catalytic chloropropoxylation reaction of carboxylic acid fractions of sunflower, olive, cottonseed, soya-bean, castor and corn oils with 2-(chloromethyl)oxirane. Colloidal-chemical parameters as well as petroleum-collecting and petroleum-dispersing capacities of the synthesized chloropropoxylate esters having heterochain of various lengths have been determined. Influence of carboxylic acid fractions composition and length of chloroxypropylene chain on petroleum-collecting and dispersing capacities has been revealed.

• Bulletin of the Korean Chemical Society
• /
• v.29 no.5
• /
• pp.1073-1074
• /
• 2008

• Bulletin of the Korean Chemical Society
• /
• v.26 no.2
• /
• pp.221-222
• /
• 2005