• Title/Summary/Keyword: Amino acid ester

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Effective Amidation of Carboxylic Acids Using (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric Acid Diethyl Ester

  • Kang, Seung-Beom;Yim, Heung-Seop;Won, Ju-Eun;Kim, Min-Jung;Kim, Jeum-Jong;Kim, Ho-Kyun;Lee, Sang-Gyeong;Yoon, Yong-Jin
    • Bulletin of the Korean Chemical Society
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    • v.29 no.5
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    • pp.1025-1032
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    • 2008
  • (4,5-Dichloro-6-oxo-6H-pyridazin-1-yl)phosphoric acid diethyl ester (3a) are efficient and selective coupling agents for the amidation of carboxylic acids. Amidation of aliphatic and aromatic carboxylic acids with aliphatic and aromatic amines using 3a under mild condition gave chemoselectively the corresponding amides in good to excellent yield. Three protected-dipeptides were also synthesized from N-BOC-Phe and O-Me-amino acid hydrochlorides using 3a under mild condition.

Studies on the Composition of Protein and Lipid from Korean Walnut (Juglans regia L.) (한국산 호도의 단백질 및 지질의 조성에 관한 연구)

  • Choi, Cheong;Sung, Tae-Soo;Cha, Woen-Suep;Son, Cyu-Mok
    • Applied Biological Chemistry
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    • v.29 no.3
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    • pp.318-323
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    • 1986
  • We empolyed gel filtraction, polyacrylamide gel electrophoresis, amino acid autoanalyzer, thin layer chromatography for determining protein and lipid composition in walnut. The walnut contained 22.18% of crude protein and 64.23% of crude lipid. Glutamic acid (38.60%) was the major amino acid in soluble protein, followed by arginine and aspartic acid. The sodium dodecyl sulfate polyacrylamide gel electrophoresis analysis showed 12 band in soluble protein of walnut, and collection rate of main protein fraction purified by Sephadex G-150 was 60.67%. The molecular weight for the main protein was estimated to be 43,000. The lipid fraction obtained by silicic acid column chromatography were mainly composed of about 93.05% neutral lipid, whereas compound lipid was only 7.0% level. Among the neutral lipid by thin layer chromatography, triglyceride was 82.05%, sterol ester and free fatty acid were 3.86% and 4.80%, repectively. The predominant fatty acids of total and neutral lipids were linoleic acid $(64.48{\sim}69.98%)$ and oleic acid $(13.89{\sim}15.36%)$. The major fatty acids of triglyceride separated from neutral lipid were linolenic acid (69.98%).

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Enhanced thermostability and substrate susceptibility of esteraseusing directed evolution

  • Choe, Gi-Seop;Kim, Ji-Hui;Kim, Geun-Jung;Yu, Yeon-U
    • 한국생물공학회:학술대회논문집
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    • 2003.10a
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    • pp.480-484
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    • 2003
  • A stereoselective-hydrolysing enzyme was cloned from Pseudomonas fluorescens KCTC1767 which had high enantiomeric activity toward (S)-ketoprofen ethyl ester. Analyses of typical properties resulted in low thermostability and substrate specificity. A round error-prone PCR and StEP(STaggered Extension Process) was adopted to evolute this character. As a result, the best clone 6-52 was selected which was represented to increased thermostability(40 fold) compared to wild type enzyme in $50^{\circ}C$. Additionally, specific activity toward (S)-ketoprofen ethyl ester and p-nitrophenyl derivatives improved 3 fold and 1.5 fold, respectively. DNA sequence analyses was showed some exchanged amino acid residue that was L120p, 1208v, T249A, D287H and T357A. Which the 120th's leucine substituted for proline was presumed structurally important residue concerning with catalytic activity.

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Polyethyleneimine Derivative for Nucleic Acid Model

  • Lee, Chan-Woo;Chae, Hee-Jeong;Kwon, Young-Jin
    • Biotechnology and Bioprocess Engineering:BBE
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    • v.10 no.3
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    • pp.205-211
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    • 2005
  • Water-soluble polyethyleneimine (PE) derivatives containing nucleic acid bases and hydrophilic amino acids such as homoserine (Hse) and serine were prepared by the activated ester method as nucleic acid models. From spectroscopic measurements, the polymers were found to interact with DNA accompanied by an induction of conformational change. Hypochromicity in UV spectra indicated that a stable polymer complex was formed between poly (A) with PEI­Hse-Ura by complementary hydrogen bonding with equimolar nucleic base units (adenine:uracil=1:1). The induced conformation of DNA by the interaction with the polymer containing uracil and homoserine (PEI-Hse-Ura) was concluded to be a super triple helical structure. The formation of the polymer complex, DNA: PEI-Hse-Ura, was found to be affected by the presence of metal ions such as $Ca^{2+}\;and\;Cu^{2+}$.

Synthetic Studies on Penems and Carbapenems(IV). Practical Preparation of (3R,4R)-4-Acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one Derivatives from 6-Aminopenicillanic Acid

  • Goo, Yang-Mo;Lee, Young-Bok;Kim, Ho-Hyun;Lee, Youn-Young;Lee, Woo-Young
    • Bulletin of the Korean Chemical Society
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    • v.8 no.1
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    • pp.15-19
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    • 1987
  • Preparation of optically pure (3R, 4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-o ne derivatives, which can be employed as starting materials for synthesis of carbapenem and penem antibiotics, was established in high efficiency from 6-amino-penicillanic acid (6-APA). 6-APA was diazotized and brominated to give 6, 6-dibromopenicillanic acid and its methyl ester was metalated with methylmagnesium bromide and condensed with acetaldehyde. The product, methyl 6-bromo-6-(1-hydroxyethyl)penicillanate was reduced with Zn-$NH_4Cl-NH_4OH$-acetone efficiently to give methyl 6-(l-hydroxyethyl)-penicillanate, which was protected either with ${\beta},{\beta},{\beta}$ -trichloroethoxycarbonyl group or with t-butyldimethylsilyl group. The thiazolidine rings of these compounds were cleaved by treatment of mercury(II) acetate in acetic acid and permangante in acetone in sequence to afford the desired optically pure final products.

Characterization and Volatile Flavor Components in Glutinous Rice Wines Prepared with Different Yeasts of Nuruks (누룩에서 분리한 효모를 이용한 찹쌀발효주의 이화학적 특성 및 휘발성 향기성분)

  • Kim, Hye-Ryun;Kwon, Young-Hee;Jo, Sung-Jin;Kim, Jae-Ho;Ahn, Byung-Hak
    • Korean Journal of Food Science and Technology
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    • v.41 no.3
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    • pp.296-301
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    • 2009
  • In order to investigate the effect of different yeasts (La Parisienne (LP), Y18-2, Y54-3, Y90-2, Y90-9 and Y272-7) from nuruks on the quality of Glutinous rice wines, physicochemical properties and volatile flavor components were evaluated. Glutinous rice wines prepared with different yeasts were analyzed for ethanol, pH, total acid, amino acid, soluble solid, coloring degree, UV absorbance, reducing sugar, organic acid, free sugar and volatile compounds. After fermentation for 17 days, the ethanol contents ranged from 13.40 to 14.50%, while the total acid levels were from 0.33 to 0.44%. The amino acid contents in six samples ranged from 0.13 to 0.18%, while soluble solid contents ranged from 12.1 to $14.7^{\circ}Bx$. The glutinous rice wine prepared with LP showed the highest level of coloring degree, soluble solid and reducing sugar among six samples. Organic acid contents of the glutinous rice wine prepared with LP had the highest levels of lactic acid and acetic acid, while the glutinous rice wine prepared with Y90-9 had the highest level of succinic acid. In all glutinous rice wines tested, the most abundant free sugars were glucose followed by maltose. Volatile flavor components in the glutinous rice wines were identified by using GC-MSD. Nineteen esters, ten alcohols, eight acids, one aldehyde and one miscellaneous compound were identified in the glutinous rice wines. Using relative peak area, it was found that other than ethyl alcohol, hexadecanoic acid ethyl ester was the major component, predominantly found in the range of 2.73-10.41%. Phenylethyl alcohol, isoamyl alcohol, ethyl oleate, ethyl linoleate and tetradecanoic acid ethyl ester were some of the major volatile components present through the fermentation, respectively. Overall, it was shown that different yeast strains from nuruks greatly affected chemical and volatile characteristics of the glutinous rice wines.

Ketoprofen ethyl ester에 대해 높은 광학 선택성을 갖는 (R)- 과 (S)-stereospecfic esterase들의 클로닝과 서열분석 및 발현

  • Kim, Ji-Yeon;Choe, Gi-Seop;Kim, Geun-Jung;Yu, Yeon-U
    • 한국생물공학회:학술대회논문집
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    • 2001.11a
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    • pp.625-628
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    • 2001
  • To isolate novel strains that hydrolyzed the rac-ketoprofen ethyl ester to ketoprofen in the stereospecific manner, we screened broad ecological niches and soil samples in which the activity was expected to be found. From thousands of strains, we isolated a Pseudomonas sp. S34 producing a (S)-stereospecific esterase, and a thermostable esterase with (R)-form selectivity was also 。 btained from Bacillus stearothermophilus JYl44. To further analyse the gene structure and to induce a high level expression, two genes from each strain were cloned and sequenced. BLAST search results with the esterase gene from 534 revealed that both of gene (80-84 %) and amino acid sequences (89- 95 %) were highly conserved in the related esterases from Pseudomonas strains (fluorescens and aeruginosa). The thermostable esterase from JY144, however, revealed a relative low homology (45-52 %) to other esterase and/or lipase from related strains. Obviously, a complete conversion with pure enantiomer (R - or S) were readily achieved by recombinant clones expressing either (R)- or (S)- stereospecific esterase.

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New Insights into 4-Amino-2-tri-fluoromethyl-phenyl Ester Inhibition of Cell Growth and Migration in the A549 Lung Adenocarcinoma Cell Line

  • Wang, Hao;Gui, Shu-Yu;Chen, Fei-Hu;Zhou, Qing;Wang, Yuan
    • Asian Pacific Journal of Cancer Prevention
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    • v.14 no.12
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    • pp.7265-7270
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    • 2013
  • Objective: The present study was designed to investigate the probable mechanisms of synthetic retinoid 4-amino-2-tri-fluoromethyl-phenyl ester (ATPR) inhibition of the proliferation and migration of A549 human lung carcinoma cells. Materials and Methods: After the A549 cells were treated with different concentrations of ATPR or all-trans retinoic acid (ATRA) for 72 h, scratch-wound assays were performed to assess migration. Immunofluorescence was used to determine the distribution of CAV1 and $RXR{\alpha}$, while expression of CAV1, MLCK, MLC, P38, and phosphorylation of MLC and P38 were detected by Western blotting. Results: ATPR could block the migration of A549 cells. The relative migration rate of ML-7 group had significantly decreased compared with control group. In addition, ATPR decreased the expression of a migration related proteins, MLCK, and phosphorylation of MLC and P38. ATPR could also influence the expression of RARs or RXRs. At the same time, CAV1 accumulated at cell membranes, and $RXR{\alpha}$ relocated to the nucleus after ATPR treatment. Conclusions: Caveolae may be implicate in the transport of ATPR to the nucleus. Change in the expression and distribution of $RXR{\alpha}$ may be implicated in ATPR inhibition of A549 cell proliferation. The mechanisms of ATPR reduction in A549 cell migration may be associated with expression of MLCK and phosphorylation of MLC and P38.

Functional Characteristics of Neutral Amino Acid Transporter in Opossum Kidney (OK) Cells

  • Woo, Jae-Suk;Park, Moon-Hwan;Oh, Sae-Ok;Jung, Jin-Sup;Kim, Yong-Keun;Lee, Sang-Ho
    • The Korean Journal of Physiology and Pharmacology
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    • v.1 no.2
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    • pp.185-193
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    • 1997
  • The characteristics of $Na^+$-dependent cycloleucine uptake was investigated in OK cells with regard to substrate specificity and regulation by protein kinase C (PKC). Inhibition studies with different synthetic and natural amino acids showed a broad spectrum affinity to neutral amino acids regardless of their different side chains including branched or aromatic, indicating that the $Na^+$-dependent cycloleucine uptake in OK cells is mediated by System $B^o$ or System $B^o$-like transporter rather than the classical System A or ASC. Phorbol 12-myristate 13-acetate (PMA) and phorbol 12,13-dibutyrate, but not $4{\alpha}-PMA$ elicited a time-dependent biphasic stimulation of $Na^+$-dependent cycloleucine uptake, which produced early transient peak at 30 min and late sustained peak at 180min. Both the early and late stimulations by PMA were due to an increase in Vmax and not due to a change in Km. PKC inhibitors blocked both the early and late stimulation by PMA, while protein synthesis inhibitors blocked the late stimulation only. These results suggest the existence and regulation by PKC of System $B^o$ or System $B^o$-like broad spectrum transport system for neutral amino acids in OK cells.

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Studies on the Preparation of Food Proteins from Castor Bean Protein (피마자 단백질의 식품화를 위한 연구)

  • Yoon, Joo-Ok
    • Korean Journal of Food Science and Technology
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    • v.12 no.4
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    • pp.263-271
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    • 1980
  • Detoxified and deallergenized castor bean protein isolate was prepared from defatted castor bean pomace for use in animal feedstuffs and human foods. Succinylation and acetylation of the ${\varepsilon}-amino$ groups of the protein improved markedly the water solubility of the protein at $pH\;7{\sim}8$. The results of the amino acid analysis of the protein isolate revealed that the sulfur-containing amino acids and L-lysine were limiting amino acids and that succinylation and acetylation caused some little loss of the amino acid content. The L-methionine enriched plastein was synthesized from the protein isolate or the acylated protein isolates and DL-methionine ethyl ester by one step process with papain. By this method the extent of incorporation of L-methionine was about 50%. Pepsin hydrolyzed both unmodified and modified protein isolates at the same rate (about 92%). Tryptic hydrolysis, however, was less for the succinylated protein isolates (about 42%) and less for the acetylated protein isolates (about 26%). The protein efficiency ratio of L-methionine enriched protein isolate (about 2.5 weight %) was 90% that of reference casein. The protein efficiency ratio values of succinylated (88%) and acetylated (84%) protein isolate were 55 and 69% of reference casein, respectively.

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