• Microbiology and Biotechnology Letters
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• v.24 no.2
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• pp.213-216
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• 1996

Optically active carboxylic acid, D-(-)-$\beta$-hydroxyisobutyric acid {(D)-(-)-HIBA} is a useful chiral starting material for the preparation of enantiomerically pure bioactive compounds which have a chiral methyl carbon center in the molecule such as captopril, $\alpha$-tocopherol, erythromycin A, muscone and so on. (S)-3-Acetoxy-2-methylpropanol can be used as the precursor of (D)-(-)-HIBA, that is, chemical oxidation of the hydroxyl group and subsequent hydrolysis of acyl group in (S)-3-acetoxy-2-methylpropanol affords D-(-)-$\beta$-hydroxyisobutyric acid. (S)-3-Acetoxy-2-methyl-propanol was prepared by lipase-catalyzed asymmetric hydrolysis. In the enzymatic hydrolysis system, lipase AY (Candida rugosa) provided the expected (S)-3-acetoxy-2-methylpropanol in 60% e.e. of the enantiomeric purity under the phosphate buffer and organic co-solvent system.

• Biotechnology and Bioprocess Engineering:BBE
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• v.7 no.3
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• pp.130-137
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• 2002

Microbial lactonohydrolases (intramolecular ester bond-hydrolyzing enzymes) with unique properties were found. The lactonohydrolase from Fusarium oxysporum catalyzes enantiose-lective hydrolysis of aldonate lactones and D-pantoyl lactone (D-PL). This enzyme is useful for the large-scale optical resolution of racemic PL. The Agrobacterium tumefaciens enzyme catalyzes asymmetric hydrolysis of PL, but the stereospecificity is opposite to that of the Fusarium enzyme. Dihydrocoumarin hydrolase (DHase) from Acinetobacter calcoaceticus is a bifunctional enzyme, which catalyzes not only hydrolysis of aromatic lactones but also bromination of monochlorodi-medon in the presence of H$_2$O$_2$and dihydrocoumarin. DHase also hydrolyzes several linear esters, and is useful for enantioselective hydrolysis of methyl DL-$\beta$-acetylthioisobutyrate and regioselective hydrolysis of methyl cetraxate.

• 한국생물공학회:학술대회논문집
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• 2005.10a
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• pp.494-494
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• 2005

• The Microorganisms and Industry
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• v.20 no.1
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• pp.23-27
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• 1994

본고에서는 화학적수법으로 다양한 특이한 기질을 제조하여 여기에 입체특이적 성질(stereospecificity)과 입체선택적 성질(steroselectivity)이 높은 생물학적 방법들 중에서 주로 lipase를 이용한 부제가수분해반응(asymmetric hydrolysis)과 그 역반응인 에스테르화반응(esterification)등을 도입한 chiral building block의 제조와 이를 이용한 곤충 생리활성물질인 pheromone의 합성에 대한 최근의 많은 예들중 상품화를 시도하고 있는 매미나방의 pheromne인 (+)-disparlure에 대하여 간단히 소개하고자 한다.

• Archives of Pharmacal Research
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• v.28 no.2
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• pp.129-141
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• 2005

(-)-Fumagillol (1), a hydrolysis product of fumagillin, has been synthesized by several group from commercially available 1,2:5,6-di-O-isopropylidene-${\alpha}$-D-allofuranose in a highly stereoselective manner. Chiral centers on C5 and C6 came from D-allofuranose and the asymmetric center on C4 was accomplished by 1,3-chirality transfer using the Claisen rearrangement on a chiral allyl alcohol. Chirality, which is necessary on an epoxide consisting of the spiro-ring system, was diastereoselectively constructed by the well-known reaction, intramolecular ester enolate alkylation (IEEA), which showed that this reaction can be applied to the alpha-alkoxy ester system. The epoxide on the side chain was regioselectively introduced by the difference between the number of substituents on the vinyl groups. This accomplishment proved that IEEA can be a useful tool for the synthesis of complex molecules.

• Applied Chemistry for Engineering
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• v.10 no.4
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• pp.515-522
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• 1999

Asymmetric polyetherimide membrane were prepared by phase inversion method, and the effects of NaOH concentration and reaction time on the morphology change of the polyetherimide membranes were studied. The morphology of skin layers varied from dense structure to sphere structure with increasing concentration of modification solution. The thickness of dense layer increased with increasing reaction time. However, when either the concentration of modifying solution was very high or the reaction time was very long, the dense layers of the asymmetric membrane were disappeared. From these results, it was found that the surface morphology of the asymmetric polyetherimide membranes depended strongly on the modification conditions such as concentration of modification solution and reaction time. These results might be explained by the hydrolysis reaction of polyetherimide into polyamic acid by the NaOH solution.

• Applied Chemistry for Engineering
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• v.10 no.2
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• pp.319-323
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• 1999

Asymmetric polyetherimide membranes were prepared by phase inversion method. In the modification of the skin layers of polyetherimide membranes, the effects of NaOH concentration on the morphology and pervaporation separation of water-isopropanol mixtures were investigated. With increasing concentration of NaOH solution, polyamicacid structure was formed by the hydrolysis of imide group of polyetherimide, and the thickness of dense layer of the asymmetric membrane increased. In the pervaporation separation of water-isopropanol mixtures the overall permeation rate decreased and the separation factor increased with increasing concentration of NaOH solution. However, when the concentration of NaOH solution was very high, the permeation rate increased but separation factor decreased. From these results, it was found that the permeation behaviors of asymmetric polyetherimide membranes depended upon the concentration of NaOH solution. These modified membranes showed that both the permeation rate and separation factor increased as the operating temperature increased.

• KSBB Journal
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• v.17 no.4
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• pp.321-325
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• 2002

Chiral epoxides are valuable intermediates for the asymmetric synthesis of enantiopure bioactive compounds. Microbial epoxide hydrolases (EHs) are newly discovered enzymes and versatile biocatalysts for the preparation of chiral epoxides by enantioselective hydrolysis of cheap and easily available racemic epoxide substrates. EHs are commercially potential biocatalysts due to their characteristics such as high enantioselectivity, cofactor-independent catalysis, and easy-to-Prepare catalysts. In this Paper, recent progresses in biochemistry and molecular biology of EH and developments of novel reaction systems are reviewed to evaluate the commercial feasibility of EH-catalyzed hydrolytic kinetic resolution for the production of chiral epoxides.

• Journal of Life Science
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• v.16 no.1
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• pp.168-174
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• 2006

Enantiopure epoxides are valuable intermediates for the asymmetric synthesis of enantiopure bioactive compounds. Microbial epoxide hydrolases (EHs) are versatile biocatalysts for the preparation of enantiopure epoxides by enantioselective hydrolysis of cheap and easily available racemic epoxide substrates. EHs are commercially potential biocatalysts due to their characteristics such as high enantioselectivity, cofactor-independent catalysis, and easy-to-prepare catalysts. In this paper, recent progresses In molecular engineering of EHs are reviewed to evaluate the commercial feasibility of EH-catalyzed hydrolytic kinetic resolution for the production of enantiopure epoxides.

• Journal of the Korean Society of Food Science and Nutrition
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• v.43 no.6
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• pp.842-853
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• 2014

For developing indigestible lipids, symmetric triacylglycerol (ST) and asymmetric triacylglycerol (AT) were produced by enzymatic interesterification using high oleic sunflower oil, palmitic ethyl ester, and stearic ethyl ester in a shaking water bath. Used enzymes were Lipozyme RMIM for ST and Lipozyme TLIM for AT. To remove ethyl ester from reactants, methanol fractionation (reactant : methanol=1:5, w/v, $25^{\circ}C$) and florisil separation (reactant : florisil=1:8, w/w) were applied. Acetone fractionation (reactant : acetone=1:9, w/v) was implemented to separate triacylglcerol (TAG) species into ST and AT. Fractions I (before fractionation), II (after fractionation, liquid phase) and III (after fractionation, solid phase) were separated from ST, whereas fractions IV (after 1st fractionation, liquid phase) and V (after 2nd fractionation, solid phase) were from AT. From sn-2 fatty acid composition analysis, the sum of palmitic acid (C16:0) and stearic acid (C18:0) was 4.9~6.5 area% in ST (I, II, III), and 41.9~43.9 area% in AT (IV, V). In vitro digestion was performed for 0, 15, 30, 60, and 120 minutes at $37^{\circ}C$ in a shaking water bath. For the digestion results, hydrolysis of V was only 40% compared to others (I, II, III, IV) at 120 minutes due to its melting point ($49^{\circ}C$). However, initially (15 minutes), hydrolysis (%) was as follows: V$32.5^{\circ}C$, $31.8^{\circ}C$) and different slip melting points ($31.3^{\circ}C$, $19.5^{\circ}C$). Even though IV has a lower TAG content composed of two saturated fatty acids than III, it had a similar melting point.