• Title/Summary/Keyword: methyl esters

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Synthesis of N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester Derivatives and their Anticancer Activity (N-(Alkyl-N'-nitrosocarbamoyl)-amino Acid Ester류의 合成 및 抗癌 作用 評價)

  • Kim, Jeong-Gyun;Park, Moon-Tae;Shin, Hong-Dae;Koh, Young-Sim;Yoon, Ung-Chan;Ryu, Sung-Ho;Moon, Kyung-Ho;Kim, Min-Sook
    • YAKHAK HOEJI
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    • v.28 no.4
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    • pp.197-206
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    • 1984
  • The derivatives of N-(alkylcarbamoyl) amino acid methyl ester, N-(2-chloroethylcarbamoyl)-glycine methyl ester (7a), -valine methyl ester (8a), -phenylalanine methyl ester (9a), N-(N'-methylcarbamoyl)-glycine methyl ester (7b), -valine methyl ester (8b), and-phenylalanine methyl ester (9b), were prepared by reacting the corresponding free amino acid methyl ester (glycine-, valine-, phenylalanine-methyl ester) with isocyanate (R-N=C=O${\cdot};R=Cl-CH_2-CH_2-or\; CH_3-)$. The prepared N-(alkylcarbamoyl) amino acid methyl esters (7,8,9) were treated with $NaNO_2$/98% HCOOH in order to obtain their nitrosoated products, N-(alkyl-N'-nitrosocarbmoyl)amino acid methyl ester. The compound (7,8,9) gave N-(2-chloroethyl-N'-nitrosocarbamoyl)-valine methyl ester (14a),-phenylalanine methyl ester (15a), N-(N'-alkyl-N'-nitrosocarbamoyl)-glycine methyl ester (13b),-valine methyl ester. (14b), and-phenylalanine methyl ester (15b) respectively under the nitrosoation. On the other hand, N-(2-chloroethylcarbamoyl) glycine methyl ester produced N-(2-chloroethylcarbamoyl)-N-nitrosoglycine methyl ester (13a). The inhibitory activity of the prepared N-(alkylcarbamoyl) amino acid methyl ester (7,8,9) and N-(alkyl-N'-nitrosocarbamoyl) amino acid methyl ester (13,14,15) towards the growth of L1210 murine leukemia cells were examined. Among them the compound (14a) and (15a) exhibit excellent activity having $ED_{50}\; to\;be\;1.5{\mu}g/ml\;and\;3.0{\mu}g/ml respectively.

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Comparative Enantiomer Separation on Chiral Stationary Phases Derived from Chiral Crown Ether by HPLC (고성능 액체 크로마토그래피에서 키랄 크라운 에테르로부터 유도된 키랄 고정상을 이용한 광학분리의 비교)

  • Huang, Hu;Jeon, So-Hee;Kim, Ji-Yeon;Lee, Won-Jae
    • KSBB Journal
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    • v.27 no.4
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    • pp.232-236
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    • 2012
  • Comparative liquid chromatographic enantiomer separation of ${\alpha}$-amino acids, their esters and primary amino compounds was performed using two chiral stationary phases (CSPs) prepared by covalently bonding (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) of the same chiral selector. In general, the separation factors and resolution factors for these analytes on CSP 1 were greater than on CSP 2, while these capacity factors on CSP 2 were quite greater than on CSP 1. Except for leucine methyl ester and phenylalanine methyl ester, the elution orders of all analytes including ${\alpha}$-amino ${\alpha}$-alkyl acids and phenylglycine alkyl esters on CSP 1 are identical to those on CSP 2. This study showed that different connecting structures for these two CSPs might influence their ability to resolve the analytes depending on their structures related to the chiral recognition mechanism.

A Study on the Biodiesel Production Technology using Lard Oil (동물성 유지를 이용한 Biodiesel 생산기술에 관한 연구)

  • Shin, Soo-Beom;Min, Byung-Wook;Yang, Seung-Hun;Park, Min-Seok;Kim, Hae-Sung;Paek, Doo-Hyeon
    • Journal of the Korean Applied Science and Technology
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    • v.23 no.1
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    • pp.19-25
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    • 2006
  • Flesh wasters from tannery create major environmental problems. Despite their considerable fat content, these waster do not find important usage. Their disposal is also troublesome and costly. We have investigated the possible use of this fat as the production of biodiesel(fatty acid methyl esters) by transesterification using with fossil fuels. The fat released the waste by boiling water under the optimal condition (i.e., temperature, $120^{\circ}C;$ decompression, 200mbar) and used to dry without refining for the production of fatty acid methyl esters. Under the optimal condition, the experimental value of biodiesel yield was about 96%. The result of the chemical and GC analysis showed fatty acid composition and characteristics of biodiesel. Evaluation of the product indicated that it was suitable for use as a biodiesel fuel. In result of this experiment oil extract from fleshing process can be transformed into an environmentally affination fuel, to provide economical and ecological profits.

Recent advance on the borylation of carbon-oxygen bonds in aromatic compounds

  • Jeon, Seungwon;Lee, Eunsung
    • Journal of Radiopharmaceuticals and Molecular Probes
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    • v.4 no.1
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    • pp.16-21
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    • 2018
  • Organoboron compounds and their derivatives are synthetically versatile building blocks because they are readily available, stable, and highly useful for potential organic transformations. Arylboronic esters are of particular interest due to their well-established synthetic methods: transition metal catalyzed borylations of aryl halides. However, the use of aryl halides as an electrophile has one serious disadvantage: formation of toxic halogenated byproducts. A promising alternative substrate to aryl halides would be phenol derivatives such as aryl ethers, esters, carbamates and sulfonates. The phenol derivatives involve several advantages: their abundance, relatively low toxicity and versatile synthetic application. However, utilization of the aryl methyl ether, which is one of the simplest phenol derivatives, remains as a challenge, as C-OMe bond activation requires high activation energy and methoxides are not good leaving groups. Nevertheless, there have been a significant recent progress on ipso-borylation of aryl methyl ether including Martin's nickel catalysis. Here, we review the current advance on the borylation of carbon-oxygen bonds of unactivated C-OMe bond in aromatic compounds.

Molecular Dynamic Simulations of the Fatty Acid Bilayer Containing Very Long Chain Transmembrane Dicarboxylic Acids

  • Choi, Yong-Hoon;Yang, Chul-Hak;Kim, Hyun-Won;Jung, Seun-Ho
    • BMB Reports
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    • v.33 no.1
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    • pp.54-58
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    • 2000
  • Recent research results regarding the very long chain transmembrane ${\alpha},{\omega}-dicarboxylic$ components in the membrane of extremophilic eubacteria, such as Sarcina ventriculi, Thennotoga maritima, and Thermoanaerobacter ethanolicus have raised interesting questions concerning the physical and biochemical function on these components in the membrane. In order to understand the dynamic characteristics of these acids which reside in the bilayer membrane, 580 ps molecular dynamic simulations at 300 K were performed for two model systems. These systems were the bilayer with regular chain (C16:0 or C18:1) fatty acid methyl esters and the fatty acid bilayer containing very long chain transmembrane dicarboxylic acid methyl esters (${\alpha},{\omega}-15,16-dimethyltriacotane-dioate$ dimethyl ester; C32:0). Our analyses indicate that very long chain transmembrane dicarboxylic acids have a noticeable influence on the bilayer dynamics at a sub-nanosecond time scale. The center-ofmass mean-squared-displacement (MSD) of regular chain fatty acids adjacent to the very long chain transmembrane dicarboxylic acids decreased, the long-axis order parameter increased, and the reorientational motions of methylene groups were slowed along the hydrocarbon chains. These results indicate that the very long chain transmembrane dicarboxylic acids reduce the molecular order of the whole bilayer membrane.

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Kinetics of the KOH Catalyzed-Methanolysis for Biodiesel Production from Fat of Tra Catfish

  • Huong, Le Thi Thanh;Tan, Phan Minh;Hoa, Tran Thi Viet;Lee, Soo
    • Journal of the Korean Applied Science and Technology
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    • v.25 no.4
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    • pp.418-428
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    • 2008
  • Transesterification of fat of Tra catfish with methanol in the presence of the KOH catalyst yields fatty acid methyl esters (FAME) and glycerol (GL). The effects of the reaction temperature and reaction time on rate constants and kinetic order were investigated. Three regions were observed. In the initial stage, the immiscibility of the Tra fat and methanol limited the reaction rate, hence this region was controlled by the mass transfer. Subsequent to this region, produced FAME like a co-solvent made the reaction mixture homogeneous, therefore the conversion rate increased rapidly so it was controlled by the kinetic parameters of the reaction until the equilibrium was approached in the final slow region. A second-order kinetic mechanism was proposed involving second regions for the forward reaction. The rate determining step for the overall KOH catalyzed-methanolysis of Tra fat was the conversion of triglycerides (TG) to diglycerides (DG). This rate constant was increased from 0.003 to $0.019min^{-1}$ when the reaction temperature was increased from 35 to $60^{\circ}C$. Its calculated activation energy was 14.379 ($kcal.mol^{-1}$).

Enantiomeric Resolution of α-Amino Acid Derivatives on Two Diastereomeric Chiral Stationary Phases Based on Chiral Crown Ethers Incorporating Two Different Chiral Units

  • Kim, Hee-Jin;Choi, Hee-Jung;Cho, Yoon-Jae;Hyun, Myung-Ho
    • Bulletin of the Korean Chemical Society
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    • v.31 no.6
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    • pp.1551-1554
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    • 2010
  • Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic ${\alpha}$-amino methyl esters, ${\alpha}$-amino N,N-diethylamides and ${\alpha}$-amino N-propylamides. The CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of ${\alpha}$-amino N-propylamides. Some of ${\alpha}$-amino methyl esters and ${\alpha}$-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.

Biodegradibility Tests of Biodiesel-derived Pentaerythritol Lubricant Oil Bases (바이오디젤 유래 펜타에리쓰리톨계 윤활유 베이스의 생분해성 테스트)

  • 정해영;김의용;채희정
    • KSBB Journal
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    • v.19 no.2
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    • pp.132-137
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    • 2004
  • Biodegradability test for various synthetic lubricant oil bases derived from biodiesel was carried out. The biodegradability was estimated under aerobic aqueous condition, according to the method by OECD 301 B, which is based on CO$_2$ evolution test. The ultimate biodegradability of pentaerythritol methyl esters were estimated as 61.1∼80.3%, at 28 day with which the test compounds were indicated as ultimately biodegradable. Among the tested samples, biodiesel showed the highest biodegradability (83.5%). The validation with several criteria, regarding relative errors of test results, toxicity control and procedure control, was performed through the biodegradability test. The test procedure was validated for all the tested lubricant oil bases and biodiesel, except for petroleum diesel.

Studies on Volatile Flavor Compounds of Soy Sauce Residue (간장박의 휘발성 향기성분에 관한 연구)

  • Cha, Yong-Jun;Wang, Wenfeng;Cha, Ha-Ram
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.45 no.12
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    • pp.1755-1761
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    • 2016
  • Volatile flavor compounds in soy sauce residue (SSR) and acid hydrolysate of SSR (AHSSR) were analyzed by solid phase micro extraction (SPME)/gas chromatography (GC)/mass spectrometry (MSD) methods. A total of 79 compounds were detected in samples (66 SSR and 60 AHSSR). Quantitatively, alcohols (433.37 ng/g), aldehydes (273.01 ng/g), esters (236.80 ng/g), and aromatic hydrocarbons (180.66 ng/g) were dominant in the volatiles of SSR, whereas furans (249.27 ng/g) were only dominant in AHSSR (P<0.05). Among these, four esters, 3-methylbutyl acetate (banana/pear-like), ethyl 3-methyl butanoate (fruity), ethylbenzene acetate (wine-like), and ethyl 3-methyl butanoate (apple-like), three alcohols, 3-methyl-1-butanol (fruity/whisky-like), 2-phenylethanol (floral/sweet), and 1-octen-3-ol (mushroom-like), four aldehydes, (E)-2-phenyl-2-butenal (chocolate-like), benzaldehyde (almond-like), 3-methylbutanal (malty), and 2-phenylacetaldehyde (floral), four aromatic hydrocarbons, 4-ethyl-2-methoxyphenol (smoky/soy sauce-like), 4-ethylphenol (medicine-like), 4-vinyl-2-methoxyphenol (woody), and phenol (woody), and two furans, furfural (almond-like) and 4-hydroxy-2,5-dimethyl-3(2H)-furanone (caramel-like), were major compounds in SSR, whereas seven compounds, including furfural, 5-methylfurfural (almond-like), 3-methyl-1-butanol, 2-phenylethanol, 4-ethyl-2-methoxyphenol, 3-methylbutanal, and benzaldehyde were major compounds in AHSSR.

Characteristics of Volatile Flavor Compounds in Improved Kochujang Prepared with Glutinous Rice Koji during Fermentation (찹쌀고오지를 사용한 개량식고추장의 숙성과정 중 휘발성 향기성분의 특성)

  • Choi, Jin-Young;Lee, Taik-Soo;Noh, Bong-Soo
    • Korean Journal of Food Science and Technology
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    • v.31 no.5
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    • pp.1221-1226
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    • 1999
  • Volatile flavor components of glutinous rice koji kochujang made by an improved method were analyzed by using a purge and trap method during fermentation and identified with GC-MSD. Twenty-one volatile flavor components detected immediately after making kochujang including 6 alcohols, 6 esters and 2 aldehydes. Forty-six volatile flavor components including 15 alcohols, 15 esters, 5 acids, 5 aldehydes, 1 alkane, 1 amine, 1 alkene and 3 others were found in an improved kochujang after 150 day of fermentation. Twenty kinds of flavor components, 5 alcohols such as ethanol, 3-methyl-1-butanol. 2-methyl-1-propanol, 6 ester such as ethyl acetate. 2-methylpropyl acetate, ethylbutanoate, phenylacetate, 2 aldehydes and 7 others were commonly found through the fermentation period. Peak area(%) of ethenone was the highest one among the volatile flavor components at immediately after mashing, and ethyl acetate showed the highest peak area after $30{\sim}60$ day of fermentation, and ethanol showed the highest peak area after $90{\sim}120$ day of fermentation, and 3-methyl-1-butanol showed the highest peak area after 150 day of fermentation(as major components). 2-Methyl-1-propanol, 1-butanol and methylbenzene were detected in glutinous rice koji kochujang during the fermentation.

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