• Title/Summary/Keyword: Enantioseparation

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Enantioseparation of Neutral Compounds on a Quinine Carbamate-Immobilized Zirconia in Reversed-Phase Capillary Electrochromatography

  • Lee, Mun-Rak;Gwon, Ju-Rim;Park, Jung-Hag
    • Bulletin of the Korean Chemical Society
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    • v.31 no.1
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    • pp.82-86
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    • 2010
  • Quinine (QN) is a weak anion-exchange type chiral selector and QN-based silica stationary phases have been widely used for enantioseparation of acidic chiral analytes in HPLC and recently in CEC. In this work we report enantioseparation of non-acidic chiral analytes on a quinine carbamate-immobilized zirconia (QNZ) in reversed-phase (RP) CEC. Influences of pH, composition of the buffer, acetonitrile content and the applied voltage on enantioseparation were examined. Enantiomers of the analytes investigated are well separated in acetonitrile/phosphate buffer mobile phases. Separation data on QNZ were compared to those on QN-bonded silica (QNS). Retention was longer but better enantioselectivity and resolution were obtained on QNZ than QNS.

Preparation of New Binaphthol Derived Chiral Stationary Phases

  • Zhang, Yi Jun;Ryoo, Jae-Jeong
    • Bulletin of the Korean Chemical Society
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    • v.32 no.8
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    • pp.2756-2760
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    • 2011
  • To develop more advanced binaphthol derived CSPs, two new 1,1-bi-2-naphthol derived chiral stationary phases (CSPs) (CSP 1 and CSP 2) were prepared by connecting with silica gel at a hydroxy (OH) group of binaphthol. Previously reported two 1,1'-binaphthyl-2,2'-diamine derived CSPs (CSP 3 and CSP 4) were also prepared to compare the role of their functional groups (-OH and -$NH_2$) with CSP 1 and CSP 2. Enantioseparation of randomly selected, 11 chiral compounds on these four CSPs was performed and the results compared to each other. 3,5-Dinitrobenzoyl (3,5-DNB) derivatives of each CSP showed better results than the others and binaphthyldiamine derived CSP showed slightly better than binaphthol derived one.

Enantioseparation of Flurbiprofen and Ketoprofen in Patches and in Urine Excretions by Achiral Gas Chromatography

  • Paik, Man-Jeong;Nguyen, Duc-Toan;Kim , Kyoung-Rae
    • Archives of Pharmacal Research
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    • v.27 no.12
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    • pp.1295-1301
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    • 2004
  • The enantiomeric composition tests on flurbiprofen and ketoprofen present in patch products and in urine excretions following patch applications were performed as diastereomeric (R)-(+)- 1-phenylethylamides by achiral gas chromatography and by gas chromatography-mass spectrometry in selected ion monitoring mode. The method for determination of (R)- and (S)-enantiomers in the range from 0.1 to 5.0 ${\mu}$g was linear (r ${\ge}$ 0.9996) with acceptable precision (% RSD ${\le}$5.2) and accuracy (% RE = 0.6 ~ -2.4). The enantiomeric compositions of flurbiprofen in one patch product and of ketoprofen in five different products were identified to be racemic with relatively good precision (${\le}$ 6.4%). The urinary excretion level of (R)-flurbiprofen was two times higher than its antipode, while the comparable excretion levels of (R)- and (S)-enantiomers for ketoprofen were observed.

Liquid chromatographic enantioseparation of several amino acids as nitrobenzoxadiazole derivatives on polysaccharide trisphenylcarbamate derived chiral stationary phases

  • Suraj Adhikari;Alisha Bhandari;Wonjae Lee
    • Analytical Science and Technology
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    • v.36 no.4
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    • pp.143-151
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    • 2023
  • Considering the greater role of α-amino acids in our daily lives, the enantiomer resolution of seven α-amino acids derivatized with fluorogenic reagent (4-fluoro-7-nitro-2,1,3-benzoxadiazole, NBD-F) by chiral HPLC on amylose or cellulose trisphenylcarbamate derived chiral stationary phases (CSPs) under simultaneous ultraviolet (UV) and fluorescence (FL) detection was performed. The degree of enantioseparation and resolution was affected by nature and selector backbones of the CSPs as well as the kind of amino acids. Baseline enantiomer separation and resolutions were observed for the enantiomers of all analytes as NBD derivatives especially on coated type amylose tris(3,5-dimethylphenylcarbamate) derived CSPs (Chiralpak AD-H and Lux Amylose-1). The other CSPs also showed good enantioselectivity except for the CSPs (Chiralpak IB, Chiralcel OD-H and Lux Cellulose-1) having cellulose tris(3,5-dimethylphenylcarbamate) as chiral selectors. The developed analytical chiral method was applied to determine the enantiomeric purity of seven commercially available L-α-amino acids and the impurities as D-forms were found to be in the range 0.08-0.87 %, respectively. The intra- and interday accuracy and precision assays showed high accuracy and precision of the developed analytical method. This chiral HPLC method for the enantiomer resolution of amino acids using fluorescent derivatization could be useful for the determination of enantiomeric purity of pharmaceuticals and biological study for amino acid type compounds among chiral drugs.

Structure Control of Polysaccharide Derivatives for Efficient Enantioseparation by HPLC

  • Okamoto, Yoshio
    • Proceedings of the Polymer Society of Korea Conference
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    • 2006.10a
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    • pp.27-28
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    • 2006
  • Chromatographic separation of enantiomers by high-performance liquidchromatography (HPLC) has considerably advanced in the past two, and many optically active polymers have been developed to be usedaschiral stationary phases (CSP). Among many CSPs, cellulose-andamylose-based CSPs are most attractive from the viewpoints of theirwide applicability and easy availability. The polysaccharides are readily modified to ester and carbamates. The derivatives have been used as CSPs after being coated on macroporus silica gel. Here, the CSPs based on phenylcarbamate derivatives of these two polysaccharides will be mainly discussed. The immobilization of the derivatives on silica gel will also be discussed.

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