• Title/Summary/Keyword: Chiral Separation

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Multidimensional Gas Chromatography-A Powerful Tool for the Analysis of Multicomponent Mixtures

  • Kim, Kyoung-Su
    • Preventive Nutrition and Food Science
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    • v.1 no.1
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    • pp.127-133
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    • 1996
  • The development of high resolution capillary columns and a large variety of different detectors led to a strong position of gas chromatography in instrumental analysis. Every effort has been made to solve sophisticated separation problems by column switching. Nowadays, several systems are commercially available for this purpose. The principle and the capabilities of multidimensional gas chromatography(MDGC) are illustrated by different applications in the field of modern flavor and essential oil research.

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Determination of nadolol enantiomers in human plasma using a coupled achiral-chiral high-performance liquid chromatography method

  • Lee, Seung-Beom;Pham, Thuy-Vy;Mai, Xuan-Lan;Le, Thi-Anh-Tuyet;Nguyen, Thi-Ngoc-Van;Kang, Jong-Seong;Mar, Woongchon;Kim, Kyeong Ho
    • Analytical Science and Technology
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    • v.33 no.2
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    • pp.59-67
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    • 2020
  • Nadolol is a β-blocker drug, which effectively manages hypertension and angina pectoris. Its chemical structure allows the formation of four possible stereoisomers. A coupled column high-performance liquid chromatographic (HPLC) system with UV and fluorescence detection was investigated for simultaneously determining four nadolol enantiomers in human plasma. The plasma samples were prepared using a convenient liquid-liquid extraction process and passed through HPLC. Nadolol was initially separated from the endogenous compounds or other impurities in human plasma on a Phenomenex silica column, and its enantiomers were resolved and determined on a Chirapak AD-H column. The developed HPLC method achieved an effective chiral separation and significantly eliminated endogenous compound interference. This optimal HPLC method was validated following FDA guidelines. The results showed good selectivity, linearity, accuracy (90.50 % - 105.27 %), and precision (RSDs < 9.52 %) for each enantiomer. This method was also successfully applied to determine nadolol enantiomers in the plasma samples of a healthy male volunteer (after orally administering 80 mg racemic nadolol), proving its suitability for nadolol stereoselective pharmacokinetic studies.

Separation Characteristics of Mandelic Acid in Kromasil HPLC Column (Kromasil HPLC 칼럼에서 Mandelic Acid의 분리특성)

  • Kim, Byung Lip;Kim, Jong Min;Kim, Woo Sik;Kim, In Ho
    • Korean Chemical Engineering Research
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    • v.46 no.4
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    • pp.681-685
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    • 2008
  • Chiral separation of racemic mandelic acid was achieved on a Kromasil KR100-5CHI-TBB column. Some chromatographic parameters (resolution, number of theoretical plates, capacity factor) are calculated under different separation conditions such as changes of mobile phase compositions (hexane/t-BME = 85/15 - 10/90) as well as formic acid concentrations for adjusting pH (0.1, 0.5, 1.0 v/v%). Flow rate versus number of theoretical plates was compared to evaluate column efficiency. To determine the adsorption isotherms, PIM (Pulse Input Method) was carried out. At the concentrations of racemic mandelic acid between 0.1 and 0.3 mg/ml, L- and D-mandelic acids have the same retention times of 8.8 and 9.4 min respectively. Mandelic acid isotherms show a linear form under the concentrations of 0.3 mg/ml with eluent (hexane/t-BME = 75/25). As the concentrations of mandelic acids increase, nonlinear Langmuir isotherms were observed as $C_{S,L}=3.358C_{M,L}/(1+0.0897C_{M,L})$ for L-mandelic acid and, $C_{S,D}=3.692C_{M,D}/(1+0.1457C_{M,D})$ for D-mandelic acid.

Enantiospecific separation in biphasic Membrane Reactors

  • Giorno, Lidietta
    • Proceedings of the Membrane Society of Korea Conference
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    • 1998.10a
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    • pp.15-18
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    • 1998
  • Membrane reactors are systems which combine a chemical reactor with a membrane separation process allowing to carry out simultaneously conversion and product separation. The catalyst can be immobilized on the membrane or simply compartmentalized in a reaction space by the membrane. Membrane reactors are today investigated to produce optically pure isomers and/or resolve racemic mixture of enantiomers. The interest towards these systems is due to the increasing demand of enantiomerically pure compounds to be used in the pharmaceutical, food, and agrochemical industries. In fact, enantiomers can have different biological activities, which often influence the efficacy or toxicity of the compound. On the basis of current literature there are basically two schemes on the use of membrane technology to produce enantiomers. In one case, the membrane itseft is intrinsically enantioselective: the membrane is the chiral system which selectively separates the wanted isomer on the basis of its conformation. In the other, a kinetic resolution using an enantiospecific biocatalyst is combined with a membrane separation process; the membrane separates the product from the substrate on the basis of their relative chemical properties (i.e. solubility). This kind of configuration is widely used to carry out kinetic resolutions of low water soluble substrams in biphasic membrane reactors [Giomo, 1995, 1997; Lopez, 1997]. These are systems where enzyme-loaded membranes promote reactions between two separate phases thanks to the properties of enzymes, such as lipases, to catalyse reactions at the org ic/aqueous interface; the two phases are maintained in contact and separated at the membrane level by operating at appropriate transmembrane pressure. A schematic representation of biphasic membrane reactor is shown in figure 1, while an example of enantiospecific reaction and product separation carried out with these systems is reported in figure 2.

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Optical Resolution of DABS-Amino Acids with Mobile Chiral Chelate Addition (키랄킬레이트 이동상첨가법에 의한 답실아미노산의 광학이성질체 분리)

  • Lee, Seon Haeng;O, Dae Seop;Byeon, Seong Gu
    • Journal of the Korean Chemical Society
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    • v.34 no.4
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    • pp.345-351
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    • 1990
  • Optical isomers of DABS-amino acids have been separated in a reversed phae high performance liquid chromatography by adding Cu (Ⅱ)-L-Proline chelate to the mobile phase. The retention behaviors for the DABS-amino acids are discussed in terms of pH of the mobile phase and the concentrations of acetonitrile, Cu (Ⅱ) complex, and buffer. The selectivity of the optical isomers of DABS-amino acids increases with the pH of the mobile, and the concentration of the chelate, but decreases with concentration of the oganic modifier. The concentration of buffer does not affect the optical separation selectivity. A separation mechanism is illustrated by cis and trans formation based on the steric effect of the ligand exchange reaction between DABS-amino acids and the copper chelate.

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SMB 크로마토그래피를 이용한 loxoprofen racemate의 분리

  • Yun, Tae-Ho;Kim, In-Ho
    • 한국생물공학회:학술대회논문집
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    • 2003.10a
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    • pp.549-553
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    • 2003
  • SMB(simulated moving bed) chromatography system has been developed to realize continuous separation and save solvent consumption for binary mixture such as chiral compounds in especial. The parameters of SMB chromatography system can be calculated from mass balance equations of true moving bed chromatography, and they are used in design of 6-column SMB chromatography. We can separate 1'R-25 and 1'S-2S enantiomers as a raffinate product in 95% of purity using assembled SMB chromatography system.

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Stereoselective Ligand Exchange Reaction of trans-dichlorocobalt(III) complex contained SS-epm and racemi propane-1,2-diamine (SS-epm이 배위된 trans-dichlorocobalt(III) 착물과 라세미 propane-1,2-diamine과의 입체선택적 리간드 치환반응)

  • Kim, Dong-Yeub
    • Journal of the Korean Society of Industry Convergence
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    • v.3 no.1
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    • pp.77-82
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    • 2000
  • The stereoselective ligand exchange reaction of trans-$[Co(SS-epm)Cl_2]^+$ and racemic propane-1,2-diamine (rac-pn) produces the complex that is identified as $[CO(N)_6]^{3+}$ type of $[Co(SS-epm)(pn)]^{3+}$ by absorption spectrum. It is conceivable that the reaction mechanism involves substitution and isomerization. The calculated and experimentally determined ratios of the complexed enantiomeric substrates at equilibrium were as follows: $[Co(SS-epm)(pn)]^{3+}$,calcd 32 % / 68 %, exptl 19 % / 81 % R-pn / S-pn. It has been shown that the employment of molecular mechanics calculations as a predictive tool may lead to the design of chiral complexes that may be applied to the separation of racemic mixtures of simple bidentate ligands.

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A Study on the development of developer for positive type presensitized off-set plates (포지용 오프셋 PS판의 현상액 개발)

  • 오세웅
    • Journal of the Korean Graphic Arts Communication Society
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    • v.16 no.1
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    • pp.1-11
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    • 1998
  • Recently the study of the application of liquid crystal in industrial fields has developed rapidly. It is well known that the encapsulated liquid crystal is advantageous than raw liquid crystal for protection of surface pollution. This paper describes a new class of thermal sensor. It is that the liquid crystal polymer composite(LCPC) films consisting of a continuous LC phase embedded in a three-dimensional network of polymer matrix are formed by photopolymerization-induced phase separation. In this works, it has been demonstrated that consiste of a 8:2 mixture of chiral nematic liquid crystal and HX-620 has the greatest domain and it was best discoloration.

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Optical Purity Determination of (S)-Ibuprofen in Tablets by Achiral Gas Chromatography

  • Paik, Man-Jeong;Kim, Kyoung-Rae
    • Archives of Pharmacal Research
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    • v.27 no.8
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    • pp.820-824
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    • 2004
  • An optical purity test was indirectly performed on (S)-ibuprofen as its diastereomeric (R)-(+)-1-phenylethylamide derivative using achiral gas chromatography (GC). The method for the determination of trace (R)-ibuprofen (optical impurity), within the range 1.0 to 50 ng, from a racemic ibuprofen standard was linear (r=0.9997) with acceptable precision (% $RSD{\leq}5.3$) and accuracy (% RE=0.7~-3.9). Similar results were obtained with the method validation for the quantification of (S)-ibuprofen within the range 0.1 to 2.0 $\mu\textrm{g}$ using a (S)-ibuprofen stan-dard. When applied to seven different commercial (S)-ibuprofen products, their optical purities (98.7~99.1%) were determined with good precision (% $RSD{\leq}4.0$).