• Title/Summary/Keyword: Chiral Selector

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Chiral Separation of Aromatic Acids by Capillary Electrophoresis Using HP $\beta$-Cyclodextrin as the Chiral Selector

  • La, Soo-Kie;Kim, Ji-Young;Kim, Jung-Han;Kim, Kyoung-Rae
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.399.2-399.2
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    • 2002
  • Capillary electrophoretic direct chiral separation method is described for the determination of the absolute configuration of chiral aromatic acids, The enantiomeric separation was achieved by capillary electrophoresis using HP $\beta$-cyclodextrin (CD) as the chiral selector. The effect of CD concentration was investigated to optimize the chiral separation and resolution. When applied to microbial culture fluid. the present method allowed positive identification of chiral aromatic acids and their chirality as well.

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Chiral discrimination studies of (+)-(18-crown-6)-2.3.11.12-tetracarboxylic acid by NMR spectroscopy

  • Lee, Won-Jae;Baek, Chae;Bang, Eun-Jung
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.399.1-399.1
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    • 2002
  • The chiral stationary phase derived from (+) (18-crown-6)-2.3, 11.12-tetracarboxylic acid (18-C-6- TA) as a chiral selector has been employed for resolution of several $\alpha$-amino acids in HPLC. In a quest for the origin of chiral recognition of $\alpha$-amino acids in the presence of 18-C-6- T, A, as a chiral selector, these interactions responsible for the differential affinities shown toward enantioners were investigated by NNR spectroscopy. (omitted)

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1Determination of optical purity of N-acetyl-1-naphthylethylamine by chiral chromatography and NMR spectroscopy (키랄 크로마토그래피와 NMR 분광법에 의한 N-acetyl-1-naphthylethylamine의 광학순도 측정)

  • Jeong, Young-Han;Ryoo, Jae-Jeong
    • Analytical Science and Technology
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    • v.23 no.1
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    • pp.97-101
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    • 2010
  • (R)-N-3,5-dinitrobenzoyl (DNB) phenylglycinol derived chiral selector was used as a HPLC chiral stationary phase (CSP) for the resolution of racemic N-acylnaphthylalkylamines. In this study, determination of optical purity was performed by both chiral chromatography and NMR spectroscopy by using the (R)-phenylglycinol derived chiral selector. The data of accuracy and precision of each optical purity value are calculated from the results of NMR and HPLC experiments by comparing with true value. Average error of the NMR method was +2.2% with average RSD of 4.54%, while that of HPLC method was -3.5% with average RSD of 3.23%.

Chiral Separation of Arylalcohols by Capillary Electrophoresis Using Sulfonated β-Cyclodextrin and Ag Colloids as Additives

  • Choi, Seong-Ho;Noh, Hyen-Ju;Lee, Kwang-Pill
    • Bulletin of the Korean Chemical Society
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    • v.26 no.10
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    • pp.1549-1554
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    • 2005
  • Chiral separation of arylalcohols such as 1-phenyl-1-propanol, 1-phenyl-2-propanol, and 2-phenyl-1-propanol by capillary electrophoresis was studied using sulfonated $\beta$-cyclodextrin (CD) as a chiral selector and Ag colloids as an additive. The optimum separation condition of arylalcohols was found to be the chiral selector concentration of 6.5 mM, applied voltage of 15 kV, and pH of 7.0. In order to improve chiral separation, an Ag colloid was mixed with a running buffer. The resolution in the Ag colloid-mixed running buffer was considerably superior to that obtained with the sulfonated $\beta$-CD alone. The molar ratio of sulfonated $\beta$-CD to Ag colloid, which is one of critical parameters affecting resolution, was found to be optimum at 65 : 1. In order to elucidate the resolution mechanism, an inclusion-complex of the arylalcohols with sulfonated $\beta$-CD was prepared by mixing and shaking in solution, and then characterized by cyclic voltammetry (CV). The inclusion mechanism was also discussed using experimental results.

Investigation of Enantiomer Separation Using Chiral Crown Ethers as Chiral Selectors

  • Lee, Wonjae
    • Journal of Integrative Natural Science
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    • v.9 no.1
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    • pp.28-34
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    • 2016
  • A number of chiral selectors have been developed and applied for enantiomer separation of a variety of chiral compounds. Among these chiral selectors are chiral crown ethers, a class of synthetic host polyether molecules that bind protonated chiral primary amines with high selectivity and affinity. In this paper, two important chiral crown ethers as chiral selectors of bis-(1,1'-binaphthyl)-22-crown-6 and (18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-TA) are focused. They have been widely used to resolve the enantiomers of chiral compounds containing a primary amino moiety using chiral stationary phases (CSPs) or chiral selectors by high-performance liquid chromatography (HPLC), capillary electrophoresis (CE) and so on in chirotechnology. Also, it was described that the commercially available covalent type HPLC CSPs derived from (+)- and (-)-18-C-6-TA have been developed and successfully applied for the resolution of various primary amino compounds including amino acids.

Comparison of liquid chromatographic enantiomer resolution of racemic amino compounds on chiral stationary phases of crown ether type

  • Lee, Won-Jae;Baek, Chae-Sun;Kim, Ji-Yeon
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.285.1-285.1
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    • 2003
  • ChiroSil RCA(+) and SCA(-) HPLC chiral stationary phases (CSPs) developed by covalently bonding (+)- and (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid (18-C-6-T A) to silica gel were employed for enantioresolution of racemic amino compounds, respectively. Also, these 18-C-6-TA covalently bonded CSPs were compared to a commercially available Crownpak CR CSP prepared by coating chiral crown ether as a chiral selector on ODS column. (omitted)

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Enantioselective Pharmacokinetics of Carvedilol in Human Volunteers

  • Phuong, Nuyen-Thi;Lee, Beam-Jin;Choi, Jung-Kap;Kang, Jong-Seong;Kwon, Kwang-il
    • Archives of Pharmacal Research
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    • v.27 no.9
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    • pp.973-977
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    • 2004
  • Carvedilol is administered as a racemic mixture of the R(+)- and S(-)-enantiomers, although they exhibit different pharmacological effects. To investigate the stereoselective pharmacoki-netics, the enantiomeric separation of carvedilol in human plasma was undertaken using capil-lary electrophoresis (CE). Resolution of the enantiomers was achieved using 2-hydoxypropyl-$\beta$-cyclodextrin as the chiral selector. Phosphate buffer (50 mM, pH 4.0) containing 10 mM of 2-hydoxypropropyl-$\beta$-cyclodextrin was used as electrolytic buffer. Achiral separation was carried out with the same electrolytic buffer without chiral selector. Following a single oral administra-tion of 25-mg carvedilol to 11 healthy, male volunteers, stereoselective pharmacokinetic analy-sis was undertaken. The maximum plasma concentrations ( $C_{max}$) were 48.9 and 21.6 ng/mL for (R)-carvedilol and (S)-carvedilol, respectively, determined by the chiral method. The profiles of the plasma concentration of (RS)-carvedilol showed $C_{max}$ of 71.5, 72.2, and 73.5 ng/mL, as determined by the CE, HPLC/FD methods and calculations from the data of the chiral method, respectively.y.y.