Comparison of monomeric and polymeric chiral stationary phases

Lee, Kwang-Pill; Choi, Seong‐Ho; Kim, Soo-Yeon; Kim, Tae-Hyuk; Ryoo, Jae Jeong; Ohta, Kazutoku; Jin, Jiye; Takeuchi, Toyohide; Fujimoto, Chuzo

doi:10.1016/s0021-9673(02)01462-0

Cited by 8 publications

(4 citation statements)

References 12 publications

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“…Up to now, several studies were performed using polymer-based CSP. 13,14 Therefore, we used N-methacryloyl-L-glutamic acid (MAGA) as a chiral selector for the preparation of polymer-based CSP in this study. The monolithic capillary column was prepared by *Correspondence to: Adil Denizli, P.K.…”

Section: Introductionmentioning

confidence: 99%

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Electrochromatographic Enantioseparation of Amino Acids Using Polybutylmethacrylate‐based Chiral Monolithic Column by Capillary Electrochromatography

Aydoğan

Deni̇zli̇

2012

Chirality

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This article describes the development of a polybutylmethacrylate-based monolithic capillary column as a chiral stationary phase. The chiral monolithic column was prepared by polymerization of butyl methacrylate (BMA), ethylene dimethacrylate (EDMA), and N-methacryloyl-L-glutamic acid (MAGA) in the presence of porogens. The porogen mixture included N,N-dimethyl formamide and phosphate buffer. MAGA was used as a chiral selector. The effect of MAGA content was investigated on electrochromatographic enantioseparation of D,L-histidine, D,L-tyrosine, D,L-phenyl alanine, and D,L-glutamic acid. The effect of acetonitrile (ACN) content in mobile phase on electro-osmotic flow was also investigated. It was demonstrated that the poly(BMA-EDMA-MAGA) monolithic chiral column can be used for the electrochromatographic enantioseparation of amino acids by capillary electrochromatography (CEC). The mobile phase was ACN/10 mM phosphate buffer (45:55%) adjusted to pH 2.7. It was observed that L-enantiomers of the amino acids migrated before D-enantiomers. The separation mechanism of electrochromatographic enantioseparation of amino acids in CEC is discussed.

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Section: Introductionmentioning

confidence: 99%

“…CSP consists of a single piece of porous matrix. Up to now, several studies were performed using polymer‐based CSP …”

Section: Introductionmentioning

confidence: 99%

Electrochromatographic Enantioseparation of Amino Acids Using Polybutylmethacrylate‐based Chiral Monolithic Column by Capillary Electrochromatography

Aydoğan

Deni̇zli̇

2012

Chirality

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“…Unfortunately, the transfer of selectors originally developed for silica-surface grafting into polymeric matrixes is far from being straightforward. Materials produced with polymerizable versions of selectors often exhibit inferior enantiomer separation characteristics as compared to the corresponding silica-grafted binders. − The loss in performance reflects to some extent the problems associated with controlling important macroscopic polymer properties, such as pore size and structure, surface area, different nonspecific binding properties, and unpredictable solvent-induced swelling behavior. ,, To a major part, however, the observed degradation in chiral recognition capacity of polymer-embedded selectors may arise from largely ignored molecular-level insufficiencies. As the incorporation of polymerizable selectors occurs in a random fashion, they will become fixed within the polymeric network in all possible orientations and environments.…”

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confidence: 99%

“…On polymerization, these undesired hetero-/homomolecular complexes may also become integrated into the macromolecular network, generating blocked and thus unproductive selector sites. The combination of these deleterious effects may result in materials displaying extremely heterogeneous binding characteristics, becoming macroscopically evident in low levels of enantioselectivity, binding capacity, and lack of peak efficiency. − The availability of procedures that allow an improved level of control over accessibility, conformational constraints, and surface representation of the polymer-embedded selectors certainly would greatly facilitate efforts to develop polymer-type chiral stationary phases.…”

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confidence: 99%

Analyte Templating: Enhancing the Enantioselectivity of Chiral Selectors upon Incorporation into Organic Polymer Environments

et al. 2005

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A simple strategy for preserving and enhancing the chiral recognition capacity of polymer-embedded chiral selectors is proposed, capitalizing on a temporary blockage of the receptor binding site with tightly binding analytes during the polymerization process. We demonstrate that the copolymerization of a quinine tert-butylcarbamate selector monomer with chiral (and achiral) 3,5-dichlorobenzoyl amino acids allows one to control to a certain extent the binding characteristics of the resultant polymeric chiral stationary phases. The structural and stereochemical requirements of the templating analytes for maximizing the chiral recognition capacity of the polymer-embedded selectors are probed. The chromatographic chiral recognition characteristics of the analyte-templated polymeric chiral stationary phases are analyzed with respect to binding capacities and affinities and compared to those obtained with a conventional silica-based surface-grafted reference material. Changes in substrate-specific enantioselectivity originating from analyte templating are also addressed.

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Hybrid polyacrylamide chiral stationary phases for HPLC prepared by surface‐initiated photopolymerization

Ciogli

D’Acquarica

Gasparrini

et al. 2010

J of Separation Science

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Two hybrid polyacrylamide chiral stationary phases (CSPs) for HPLC have been synthesized by a new surface-initiated photo-induced radical polymerization approach of enantiopure N,N'-diacryloyl derivatives of (1R,2R)-diaminocyclohexane (CSP1) and (1R,2R)-diphenylethylenediamine (CSP2). This system is based on the activation of mesoporous silica microparticles by chemically bonded trichloroacetyl groups and dimanganese decacarbonyl as catalyst. UV irradiation was performed using a lab-made quartz photochemical reactor, ad hoc designed for the photo-induced polymerization process on the surface of microparticles. The two phases were evaluated and compared as chromatographic supports for the enantioselective HPLC of model chiral compounds. Their physico-chemical properties and chromatographic performances were also evaluated in comparison with those exhibited by the homologue CSPs obtained by the grafting-from thermal-induced process (CSP3 and CSP4). The new photopolymerization approach yielded higher grafting density than the thermal-induced one, especially in the case of the less reactive monomer (the diacryloyl derivative of (1R,2R)-diphenylethylenediamine), good chromatographic efficiency and a broad application field under normal phase and polar organic mode conditions.

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Comparison of monomeric and polymeric chiral stationary phases

Cited by 8 publications

References 12 publications

Electrochromatographic Enantioseparation of Amino Acids Using Polybutylmethacrylate‐based Chiral Monolithic Column by Capillary Electrochromatography

Electrochromatographic Enantioseparation of Amino Acids Using Polybutylmethacrylate‐based Chiral Monolithic Column by Capillary Electrochromatography

Analyte Templating: Enhancing the Enantioselectivity of Chiral Selectors upon Incorporation into Organic Polymer Environments

Hybrid polyacrylamide chiral stationary phases for HPLC prepared by surface‐initiated photopolymerization

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