• 생약학회지
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• 제17권1호
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• pp.67-72
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• 1986

A stereospecific synthesis of 3-methyl-5-(1-hydroxy-4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid (abscisic acid) from ${\alpha}-ionone$ has been investigated. Ethyl 5-(2,6,6-trimetyl-2-cyclohexen-1-yl)-trans-4-penten-2-ynoate $({\alpha},{\beta}-acetylenic\;ester)$, which was synthesized from alpha-ionone in two steps, was stereospecifically converted in good yield into ethyl 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2, 4-pentadienoate $({\alpha}-ionylideneacetate)$ by the conjugate addition of lithium dimethylcuprate at $-78^{\circ}C$. Basic hydrolysis of the ethyl ${\alpha}-ionylideneacetate$ gave an abscisic acid precursor, 3-methyl-5-(2,6,6-trimethyl-2-cyclohexen-1-yl)-cis, trans-2,4-pentadienoic acid, which can be oxidized to yield abscisic acid.

• 대한화학회지
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• 제47권4호
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• pp.354-362
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• 2003

Xestoquinone의 퓨란-접합된 4환계화합물에 대한 합성전략을 모델연구를 통하여 조사하였다. 출발물질로서 3-butyn-1-ol을 이용하여, 5-iodo-1-methoxymethoxypentyne(5)이 5단계를 거쳐 제조되었다. Ethyl 2-phenylpropanoate와 5의 반응으로부터 ethyl 7-methoxymethoxy-2-methyl-2-phenyl-5-heptynoate(6)가 88%의 수득율로 얻어졌으며, 6으로부터 중요한 중간체인 methyl 9-oxo-4-methyl-4-phenyl-2,7-nonadiynoate(13)가 6단계를 거쳐 합성되었다. 13의 분자내 고리화반응은 5%의 수득율로 isobenzofuran 14을 생성하였으며, Lewis acid 존재 하에서 4환고리 구조로 전환되었다.

• Journal of Microbiology and Biotechnology
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• 제15권6호
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• pp.1183-1188
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• 2005

Several lipases of commercial grade were screened to catalyze the methanolysis of castor oil, and an immobilized Candida antarctica (Novozym 435) had the highest activity among the lipases tested. To enhance the yield of methyl ricinoleate, several reaction parameters were optimized. The optimum temperature was $50^{\circ}C$, and the original water content of lipase was sufficient to maintain the activity of lipase, and additional water supplied inhibited the methanolysis of castor oil. Because the lipase was deactivated by methanol, the reaction was tested by three-step addition of 1 molar equivalent of methanol to the oil. However, the oil was not completely converted to its methyl esters. The final reaction mixture using 3 molar equivalents of methanol to the oil consisted of $70\%$ methyl ricinoleate, $18\%$ monoricinoleate, $11\%$ diricinoleate, and trace triricinoleate at the equilibrium state. The yield of methyl ricinoleate was $97\%$ at 6 molar ratio of methanol to the oil with 300g of castor oil and 6g of immobilized Candida antarctica at $50^{\circ}C$ within 24 h.

• 공업화학
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• 제9권5호
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• pp.749-753
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• 1998

고급지방산 메틸에스테르의 일종인 dodecanoic acid methyl ester (DME)에 금속 산화물인 고체촉매 (W-7)를 이용하여 고온, 고압하에서 ethyleneoxide (EO)를 5, 7, 9, 및 12 몰씩 부가반응시켜 얻은 비이온성 계면활성제인 methoxy polyoxy ethylene dodecanoate (MPD)류 4종을 높은 수율 (93~97%)로 합성하여 얻었다. DME는 구조적으로 활성수소가 없어서 일반적인 산, 알칼리 촉매에서는 반응이 어렵고 활성고체촉매를 사용해야 EO의 단위 몰수를 부가 시킬 수 있었다. 최종 생성물에 대한 것을 IR, HPLC 및 $^1H$ NMR를 이용하여 각각의 화합물에 대한 구조를 확인하였다. 이 결과 EO의 부가 몰수는 5.2, 7.1, 9.2 및 12.1 몰이었고, 각 몰의 평균 EO 분포는 polyoxyethylene alkyl ether (AE)처럼 정규분포 곡선을 나타내었다.

• 대한화학회지
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• 제8권4호
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• pp.153-157
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• 1964

Chloromethylation, malonic ester 합성법 및 decarboxylation에 의한 중간체들을 거친 tert.-butyl ${\beta}$-(o-tolyl)-perpropionate 치환체들의 합성을 기술하였다. 심하지 않은 치환기효과를 나타내는 bromo-, chloro- 및 methyl- 기를 가진 중간체들은 좋은 수율로 얻어져서 목적한 바 과산화 ester들을 얻었으나 nitro기를 가진 중간체는 극히 적은 수율로 얻어졌고 한편 센 electron donating effect를 나타내는 group로 치환된 toluene들의 chloromethylation은 polymerize하는 결과를 가져왔다.

• KSBB Journal
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• 제23권4호
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• pp.335-339
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• 2008

Biodiesel is an alternative and renewable energy source, which is hoped to reduce global dependence on petroleum and environmental problem. Biodiesel produced from a variety of oil sources such as vegetable oil, animal fat and waste oils, and has properties similar to those associated with petro-diesel, including cetane number, volumetric heating value, flash point, viscosity and so on. In this study, we investigate the effect of quality of raw materials on alkali-catalyzed transesterification for producing of biodiesel. The increase of content of free fatty acid and water in oil were caused the sharp decrease of conversion yield. Also, the low purity of methanol in reactant was inhibited the reaction rate. In the case of addition of sodium sulfate as absorbent to prepare catalyst solution, the content of fatty acid methyl ester in product was increased more about 1.6% than that of control. However, the addition of zeolite, sodium chloride and sodium sulfate as absorbent in reactant to remove water generated from reaction did not show any enhancement in the reaction yield. This result may provide useful information with regard to the choice and preparation of raw materials for more economic and efficient biodiesel production.

• Journal of Microbiology and Biotechnology
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• 제26권9호
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• pp.1579-1585
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• 2016

Sugar esters are valuable compounds composed of various sugars and fatty acids that can be used as antibacterial agents and emulsifiers in toothpaste and canned foods. For example, fructose fatty acid esters suppress growth of Streptococcus mutans, a typical pathogenic bacterium causing dental caries. In this study, fructose laurate ester was chosen as a target material and was synthesized by a transesterification reaction using Candida antarctica lipase B. We performed a solvent screening experiment and found that a t-butanol/dimethyl sulfoxide mixture was the best solvent to dissolve fructose and methyl laurate. Fructose laurate was synthesized by transesterification of fructose (100 mM) with methyl laurate (30 mM) in t-butanol containing 20% dimethyl sulfoxide. The conversion yield was about 90%, which was calculated based on the quantity of methyl laurate using high-performance liquid chromatography. Fructose monolaurate (M_r 361) was detected in the reaction mixture by high-resolution mass spectrometry. The inhibitory effect of fructose laurate on growth of oral or food spoilage microorganisms, including S. mutans, Bacillus coagulans, and Geobacillus stearothermophilus, was evaluated.

• 대한화학회지
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• 제5권1호
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• pp.38-41
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• 1961

By varying groups on biologically active molecules, it is possible to produce analogues which sometimes inhibit the action of the parent compound. Such is true of taurine(${\beta}$-amino-ethane sulfonic acid)as an analogue of ${\beta}$-alanine and of pantoyl taurine for pantothenic acid. It seemed possible that the sulfonic acid analogues of amino acids built into peptides might possibly produce inhibition of the parent peptide. Tauryl-L-histidine was selected to prepare as an analogue of carnosine(${\beta}$-alanyl-L-histidine). There were several reasons for this choice. Camosine causes a slight contraction of isolated uterine muscle and inhibition of this action can be easily tested. Also, taurine, being a ${\beta}$-amino sulfonic acid, is much more stable than the ${\beta}$-amino sulfonic acids. Phthalyl tauryl-L-histidine methyl ester was prepared by condensing phthalyl tauryl chloride with histidine methyl ester in chloroform. The yields were quite low possibly due to reaction between the acid chloride and the imidazole of histidine. Approximately 50 per cent yield of crude amorphous product was obtained, but upon purification by crystallization they yielded only 25 percent of a pure product. The methyl ester was removed by acid hydrolysis to prevent partial cleavage of the phthalyl group. Crystalline tauryl histidine was then obtained from this acid by removal of the phthalyl group by hydrazinolysis. Tests for inhibition were carried out by comparing the action of camosine on isolated uterine muscle before and after tauryl histidine had been added to the bath surrounding the muscle strip. Only in very high relative concentrations of tauryl histidine was there any demonstrable inhibition.

• 한국미생물·생명공학회지
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• 제20권1호
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• pp.61-67
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• 1992

유기용매 이상계에서의 thermolysin을 사용하여 아스파탐 전구체 합성시 pH, 온도, 기질농도, 그리고 유기용매상에 대한 수용액상의 부비피 ($\alpha$)등의 변화에 따른 기질의 분해 반응, 효소의 안정성, 그리고 Z-APM 합성에 미치는 복합적인 영향을 조사함으로써 반응조건의 최적화를 도모하였다. 유기용매 이상계에서의 L-PM.HCL의 자연분해는 수용액에서보다 훨씬 느리게 일어나며, 또한 $\alpha$가 증가할 수록 분해속도가 감소하는 것을 알 수 있었다.

• Archives of Pharmacal Research
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• 제14권4호
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• pp.319-324
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• 1991

2,6-Dimethyl-4-(3'-nitrophenyl)-3-methoxylaminocarbonyl-1,4-dihydropyridine-5-carboxylic acid methylester, 3b reacted with 2-cyanoethanol or benzylalcohol to give the corresponding cyanoethylurethane compound 6c in 40.6% yield and benzylurethane compound 6d in 32% yield. The cyanoethylurethane 6c was hydrolized in ethanolic NaOH to give 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-amino-5-carboxylic acid 5-methyl ester. HCl 8 in 64.8% yield. Another acid hydrolysis of benzylurethane 6d gave 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3-amino-5-carboxylic acid 5-methylester. HBr 11 in 54.7% yield.