• Bulletin of the Korean Chemical Society
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• v.8 no.6
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• pp.457-459
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• 1987

Racemic N-benzylaspartic acid (4) was prepared from maleic anhydride and used to modify and develop some efficient methods for the preparation of N-benzylaspartic anhydride hydrobromide (5). Thus, successive treatment of the compound 4 with 30% HBr in acetic acid and acetic anhydride afforded the title compound 5 in 75% yield. From this compound 5, ${\alpha}$-benzyl and ${\alpha}$-methyl N-benzylaspartates were also prepared.

• Analytical Science and Technology
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• v.15 no.6
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• pp.529-533
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• 2002

The separation and determination method of racemic isomers of flurbiprofen in urine samples have been investigated using column switching- HPLC, which include the sample treatment and concentration column. The optical rotation of two isomers separated were measured to identify d-form and l-form. The calibration curves are liear in the ranges of $0.11-5.4{\mu}g/mL$ for both d-form and l-form. The detection limits were $0.031{\mu}g/mL$ for l-isomes and $0.027{\mu}g/mL$ for d-isomer. The coefficients of variation of intra-day and inter-day precision of this method were about 1.8%. The present method was apllied to determine the concentration of racemic isomers in urine sample from human eating the drug.

• Bulletin of the Korean Chemical Society
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• v.28 no.9
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• pp.1545-1548
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• 2007

This paper discusses the racemic and stereoselective synthetic route for novel 4'α -methyl and 6'α -methyl analogues of abacavir. The quaternary carbon at the 4'-position of carbocyclic nucleoside was installed successfully via a Claisen rearrangement. The stereocontrolled construction of a methyl group in the 6'α - position was directed through the Felkin-Anh rule. A Bis-vinyl compound 9 was cyclized successfully using Grubbs' catalyst II to provide a carbocycle nucleus for the target compound. The synthesized compound 15 showed moderate anti-HIV activity (EC50 = 10.67 μM, MT-4 cell lines).

• Bulletin of the Korean Chemical Society
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• v.28 no.10
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• pp.1645-1650
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• 2007

This paper describes a racemic and stereoselective synthetic route for a novel cyclohexenyl carbocyclic adenine analogue. The required stereochemistry of the target compound was controlled using a stereoselective glycolate Claisen rearrangement followed by α-chelated carbonyl addition. The introduction of 6-chloropurine was achieved using Mitsunobu conditions, and further modifications of the corresponding heterocycle gave the target cyclohexenyl nucleoside.

• YAKHAK HOEJI
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• v.42 no.6
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• pp.576-582
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• 1998

Fenfluramine, an anorectic agent, is widely abused as a diet pill in Korea because it is freely marketed in China without any regulation. The optical isomers of fenfluramine hav e different phamacological actions: d-form is used as an anorectic agent, while l-form as a neuroleptic agent. To investigate the metabolism when racemic fenfluramine was administered orally, the urinary excretion of fenfluramine was studied in rats. The enantiomeric separation of fenfluramine was performed on achiral column by gas chromatography using (S)-N-(trifluoroacetyl)-l-prolyl chloride (TFP) as a derivatizing agent. After administration of 15mg/kg of racemic fenfluramine to rats, d-, l-fenfluramine and its metabolites d- and l norfenfluramine in urine were determined by chromatographic separation of TFP derivatives on DB-1 at retention time of 11.2, 11.8, 8.4 and 8.6 min respectively. Urinary recoveries of d and l-fenfluramine in rat were 0.42-5.9O% and 0.18-1.20% respectively in urine specimens collected during first 24hr. The comparison in the levels of isomers showed that d- fenfluramine were higher than l-form, while d-norfenfluramine were lower than l-form. The ratios between parent compound and metabolite revealed that d-norfenfluramine to d-fenfluramine ranged from 1.0 to 4.4, while the ratio of l-norfenfluramine to l-fenfluramine was 8.2-21.1 indicating that l-fenfluramine is metabolized faster than the d-isomer.

• Bulletin of the Korean Chemical Society
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• v.33 no.5
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• pp.1715-1718
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• 2012

2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

• Biotechnology and Bioprocess Engineering:BBE
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• v.9 no.4
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• pp.285-291
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• 2004

A simulated moving bed (SMB) chromatography system is a powerful tool for preparative scale separation, which can be applied to the separation of chiral compound. We have de-signed our own lab-scale SMB chromatography using 5 HPLC pumps, 6 stainless steel columns and 4 multi-position valves, to separate a racemic mixture of ketoprofen in to its enantiomers. Our design has the characteristics of the low cost for assembly for the SMB chromatography and easy repair of the unit, which differs from the designs suggested by other investigators. It is possible for the flow path through each column to be independently changed by computer control, using 4 multi-position rotary valves and 5 HPLC solvent delivery pumps. In order to prove the operability of our SMB system, attempts were made to separate the (S)-ketoprofen enantiomer from a ketoprofen racemic mixture. The operating parameters of the SMB chromatography were calculated for ketoprofen separation from a batch chromatography experiment as well as by the triangle theory. With a feed concentration of 1 mg/mL, (S)-ketoprofen was obtained with a purity of 96% under the calculated operating conditions.

• Current Research on Agriculture and Life Sciences
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• v.10
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• pp.99-108
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• 1992

This experiment was conducted to investigate biological activity of ABA and its analogues on barley shoot growth and peroxidase activity in barley seedlings. The treatments of 3.2 ppm (+)-ABA, 1.2 ppm (S)-(+)-ABA, 0.6 ppm ABA-methyl cinnamate ester compound (AC), and 0.08 ppm ABA-umbelliferone ester compound (AU) inhibited the growth of barley seedlings by more than 80% as compared with untreated control. The increase in barley shoot-inhibit activity of (S)-(+)-ABA became 3-fold than the activity of racemic ABA, and those of AC and AU higher than that of (S)-(+)-ABA by about 2.5 and 16 times, respectively. Peroxidase activities of barley shoots during the early growth stage were kept at a constant levels without ABA treatment, but in the treatment of racemic ABA, (S)-(+)-ABA, AC and AU increased the activities. Furthermore, the peroxidase activities increased as the higher concentration of ABA and its analogues were applied.

• 한국해양학회지
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• v.29 no.2
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• pp.171-182
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• 1994

Dissolved free amino acid (DFAA) dissolved hydrolyzable amino acid (DHAA) and D/L amino acid racemic ratio in the dissolved organic compounds were studied to investigate the biogeochemical characteristics of dissolved organic compound in the Yellow Sea. Concentration of total DFAA ranged from 0.06 uM to 0.26 uM in the study area. DFAA composition showed that aspiratae, glutamate, serine, glycine and alanine were predominant. According to characteristics of functional group of amino acid, these belonged to hydroponic group. C-18 short column cartridge (Sep-Pak) activated by methanol was used to extract organic macromolecules in the seawater. In operational scheme, macromolecules were divided into two fractions. Geomacromolecule fraction eluted with 50% methanol was used to extract organic macromolecules in the seawater. In operational scheme, macromolecules were divided into two fractions. Geomacromolecule fraction eluted with 50% methanol was moderately hydrophilic and showed characteristics of humic substance in the seawater. Biomacromolecule fraction eluted with 100% methanol was hydrophobic and most abundant in the surface seawater samples. DHAA was much higher than DFAA in this study area. DHAA ranged from 2.05 uM to 6.19 uM in the B-fraction and from 8.13 uM to 24.46 uM in the G-fraction. DHAA was higher in the surface water than in the bottom water where the vertical stratification developed well. The result of HPLC analysis of D/L amino acid showed that low racemic ratio was found in the B-fraction. It implies that the B-fraction is relatively younger than the G-fraction and freshly derived from biosphere.

• Bulletin of the Korean Chemical Society
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• v.26 no.10
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• pp.1520-1524
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• 2005

This paper describes the racemic and stereoselective synthetic route for a novel 4'$\alpha$-phenyl and 6'$\alpha$-methyl doubly branched carbocyclic nucleosides from an acyclic 2-hydroxy acetophenone. The installation of phenyl group at the 4'-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement. The stereoselective introduction of a methyl group in the 6'$\alpha$-position was accomplished by Felkin-Anh controlled alkylation. Bis-vinyl 11 compound was successfully cyclized using a Grubbs’ catalyst II to desired carbocycles. The natural bases (adenine and cytosine) were efficiently coupled using a Pd(0) catalyst. Although all the synthesized compounds were examined for their activity against several viruses such as HIV-1, HSV-1, HSV-2 and HCMV, only cytosine analogues 17 exhibited weak antiviral activity against HCMV.