Preparation of a permethylated β-cyclodextrin chiral stationary phase by one-pot hydrosilylation and immobilization at the C2 position for chiral high-performance liquid chromatography.

A novel cyclodextrin intermediate, mono-2(A)-allylcarbamido-2(A)-deoxy-permethylated β-cyclodextrin, was synthesized by reacting allylamine and newly prepared mono-2(A)-azido-2(A)-deoxy-permethylated β-cyclodextrin by the Staudinger reaction and anchored onto porous silica beads by a one-pot hydrosilylation and immobilization procedure to afford a novel chiral stationary phase. This stationary phase acts as a new member of the previous chiral stationary phase series immobilized on the cyclodextrin C2 position. This stationary phase depicted enantiomeric separation abilities toward a series of bicyclic and tricyclic racemates under reversed-phase conditions.

Evaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography.

In this study, perphenylcarbamated cyclodextrin clicked chiral stationary phase (CSP) was developed with high column efficiency. The characteristics of the column were evaluated in terms of linearity, limit of detection and limit of quantification. The enantioselectivity of the as-prepared clicked CSP was explored with 26 recemates including aryl alcohols, flavanoids and adrenergic drugs in reversed phase high-performance liquid chromatography.

Hydroxyethylammonium monosubstituted cyclodextrin as chiral selector for capillary electrophoresis.

A novel cationic cyclodextrin, mono-6(A)-(2-hydroxyethyl-1-ammonium)-6(A)-β-cyclodextrin chloride (HEtAMCD) has been successfully synthesized and applied as chiral selector in capillary electrophoresis. The NMR study revealed this chiral selector has three recognition sites: β-CD, ammonium cation and hydroxy group in the sidearm to contribute three corresponding driving forces including inclusion complexation, electrostatic interaction and hydrogen bonding. The effect of buffer pH and HEtAMCD concentration (2.

Hydrophilic interaction chromatography coupled matrix assisted laser desorption/ionization mass spectrometry for molecular analysis of organic compounds in medicines, tea, and coffee.

Natural occurring organic compounds from food, natural organic matter, as well as metabolic products have received intense attention in current chemical and biological studies. Examination of unknown compounds in complex sample matrices is hampered by the limited choices for data readout and molecular elucidation. Herein, we report a generic method of hydrophilic interaction chromatography (HILIC) coupled with matrix assisted laser desorption/ionization mass spectrometry (MALDI-MS) for the rapid characterization of ingredients in pharmaceutical compounds, tea, and coffee.

Enantioselective separation of dansyl-DL-amino acids and some racemates on "click" functionalized native α-cyclodextrin based sub-2 μm columns.

The current work demonstrates that native α-cyclodextrin, anchored onto sub-2 μm silica particles via "click" reactions and packed into a 5 cm column, was found to be effective for the resolution of 11 pairs of dansyl-DL-amino acids (DAAs) using ultra-high performance liquid chromatography (UHPLC). All DAAs were completely or partially separated on the column and the resolution achieved for 7 pairs of DAAs was significantly greater than 1.5.

HPLC enantioseparation on cyclodextrin-based chiral stationary phases.

Cyclodextrin-bonded silica material is one of the most commonly used chiral stationary phases in liquid chromatography for pharmaceutical analysis and enantioseparations. The approaches for immobilization of cyclodextrins onto the silica surface influence both, the stability of the chiral stationary phase and the enantioselectivity. In this chapter, we describe an established example of the preparation of a cyclodextrin-based chiral stationary phase via "click chemistry" and their application for enantioseparations of racemic compounds by HPLC.

Recent development of cyclodextrin chiral stationary phases and their applications in chromatography.

The current article reviews the development and applications of novel cyclodextrin chiral stationary phases (CD-CSPs) in liquid chromatography (LC), capillary electrochromatography (CEC), gas chromatography (GC) and supercritical fluid chromatography (SFC) over the period of January 2007 to March 2012. The synthetic routes of CD-CSPs, as well as the presence of selective functional groups in effecting inclusion complexation and molecular interactions have been found to exert profound influence in the enantioseparation process. In this article, various synthetic and functional groups immobilization strategies of novel CD-CSPs, and their applications in chiral resolution using different chromatography techniques are discussed.

Preparation and chiral separation of a novel immobilized cellulose-based chiral stationary phase in high-performance liquid chromatography.

The chiral selector 6-azido-2, 3-di(p-chlorophenylcarbamoylated) cellulose was synthesized and further chemically immobilized onto 5-μm amino functionalized spherical porous silica gel. It was used as chiral stationary phase in high-performance liquid chromatography. Thirty racemates were successfully separated into enantiomers in either normal phase mode or reversed-phase mode.

Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography.

Two covalently bonded cationic β-CD chiral stationary phases (CSPs) prepared by graft polymerization of 6(A)-(3-vinylimidazolium)-6-deoxyperphenylcarbamate-β-cyclodextrin chloride or 6(A)-(N,N-allylmethylammonium)-6-deoxyperphenylcarbamoyl-β-cyclodextrin chloride onto silica gel were successfully applied in high-performance liquid chromatography (HPLC). Their enantioseparation capability was examined with 12 racemic pharmaceuticals and 6 carboxylic acids. The results indicated that imidazolium-containing β-CD CSP afforded more favorable enantioseparations than that containing ammonium moiety under normal-phase HPLC.

Chemically bonded cationic β-cyclodextrin derivatives and their applications in supercritical fluid chromatography.

Cationic β-cyclodextrin (CD) perphenylcarbamoylated derivatives were chemically bonded onto vinylized silica using a radical co-polymerization reaction. The derived materials were used as chiral stationary phases (CSP) in supercritical fluid chromatography (SFC). Enantioseparations were successfully demonstrated on 14 racemates encompassing flavanones, thiazides and amino acid derivatives.

Sub-2 μm porous silica materials for enhanced separation performance in liquid chromatography.

Fully or partially sub-2 μm porous silica materials have garnered strong interests as column packing materials in separation and analytical technologies due to the promise of rapid separation, enhanced efficiency and separation resolution. Silica support materials of different morphology and sub-2 μm size have been developed to improve separation performances in liquid chromatography (LC) and capillary electrochromatography (CEC). The current review highlights the recent development of sub-2 μm fully/partially porous silica materials and the demonstrations of their enhanced performance in achiral and chiral chromatography.

Novel cyclodextrin chiral stationary phases for high performance liquid chromatography enantioseparation: effect of cyclodextrin type.

Three novel chiral stationary phases (CSPs) were prepared by regioselective chemical immobilization of mono(6(A)-N-allylamino-6(A)-deoxy)perphenylcarbamoylated (PICD) α-, β-, and γ-cyclodextrins (CDs) onto silica support via hydrosilylation. Their enantioseparation properties in high performance liquid chromatography (HPLC) were evaluated with a large spectrum of racemates including flavanone compounds, β-adrenergic blockers, amines and non-protolytic compounds. The effect of CD's cavity size on enantioseparation abilities was studied and discussed.

Preparation of cyclodextrin chiral stationary phases by organic soluble catalytic 'click' chemistry.

We describe an effective and simple protocol that uses click chemistry to attach native β-cyclodextrin (β-CD) to silica particles, resulting in a chiral stationary phase (CCNCSP) that can be used for the enantioseparation of chiral drugs by high-performance liquid chromatography (HPLC). Starting from β-CD, the CCNCSP is prepared in several steps: (i) reaction of β-CD with 1-(p-toluenesulfonyl)-imidazole to afford mono-6-toluenesulfonyl-β-CD; (ii) azidolysis of mono-6-toluenesulfonyl-β-CD in dimethylformamide to give mono-6-azido-β-CD (N(3)-CD); (iii) reaction of cuprous iodide with triphenylphosphine to form an organic soluble catalyst CuI(PPh(3)); (iv) preparation of alkynyl-modified silica particles; and (v) click chemistry immobilization of N(3)-CD onto alkynyl-modified silica to afford the desired chiral stationary phase. Synthesis of the stationary phase and column packing takes ∼1 week.

Resonance energy transfer (RET)-Induced intermolecular pairing force: a tunable weak interaction and its application in SWNT separation.

This paper explores evidence of an optically mediated interaction that is active in the separation mechanism of certain selective agents through consideration of the contrasting selective behaviors of two conjugated polymers with distinct optical properties. The involvement of a RET-induced intermolecular pairing force is implied by the different illumination response behaviors. The magnitude of this interaction scales with the external stimulus parameter, the illumination irradiance (I), and thus is tunable.

Novel β-cyclodextrin chiral stationary phases with different length spacers for normal-phase high performance liquid chromatography enantioseparation.

Cyclodextrin and its derivatives are widely used as selectors of chiral stationary phases (CSPs) for high performance liquid chromatography (HPLC) due to their unique molecular structure and resolution capability. Three mono(6(A)-N-(ω-alkenylamino)-6(A)-deoxy)perphenylcarbamoylated β-cyclodextrin (PICD) based CSPs with different length spacers have been prepared, with their enantioseparation abilities evaluated with 10 model racemates including aromatic alcohols, flavanone compounds, amine and non-protolytic compounds under normal-phase conditions. The effect of spacer length and surface loading on the enantioseparation performance of CSPs is investigated herewith.

Enantioseparation of dansyl amino acids by ultra-high pressure liquid chromatography using cationic β-cyclodextrins as chiral additives.

This work reports the application of ultra-high pressure liquid chromatography (UHPLC) for reasonably fast enantiorecognition of some dansyl amino acids by employing three cationic β-cyclodextrins (β-CDs) as chiral additives. Good resolutions were obtained on an Agilent C18 column (2.1 mm i.

"Click" preparation of hindered cyclodextrin chiral stationary phases and their efficient resolution in high performance liquid chromatography.

This communication reports the preparation of two new cyclodextrin (CD) chiral stationary phases (CSPs): heptakis(6-deoxy-6-azido)-β-CD and heptakis(6-deoxy-6-azido-phenylcarbamoylated)-β-CD CSPs that perform quite differently to our previously reported "click" immobilized CD-CSPs. These CSPs are sterically congested at the narrow mouth of the CD and exhibit chiral discrimination between over 40 pairs of enantiomers in high performance liquid chromatography. The free hydroxyl CSP afforded better separation of indoprofen, ketoprofen, Tröger's base, hydroxyl, carboxylic and dansyl amino acids than did the phenylcarbamoylated CSP, while the latter was better at resolving aryl alcohols, flavonoids, β-blockers and β-agonists.

Sub-1-micron mesoporous silica particles functionalized with cyclodextrin derivative for rapid enantioseparations on ultra-high pressure liquid chromatography.

Mesoporous silica particles of relatively uniform sub-1-micron size (0.6-0.9 μm) were successfully prepared by a modified synthesis strategy and applied in chiral separation in an ultra-high pressure liquid chromatography system.

"Click" immobilized perphenylcarbamated and permethylated cyclodextrin stationary phases for chiral high-performance liquid chromatography application.

Two cyclodextrin-based chiral stationary phases have been prepared by immobilization of functionalized mono-6-azido-beta-CD derivatives to alkynyl modified silica via "click" chemistry and applied to the HPLC enantioseparation of various chiral compounds. The perphenylcarbamated CD CSP (CCP-CSP) exhibited excellent chiral recognition of a wide range of analytes including racemic aryl alcohols, flavonoids, bendroflumethiazide, atropine and some beta-blockers. Methanol proved to be a better organic modifier than acetonitrile for most of the analytes with the exception of bendroflumethiazide.

Chiral capillary electrophoresis with cationic pyrrolidinium-beta-cyclodextrin derivatives as chiral selectors.

New single-isomer, cationic beta-cyclodextrins, including mono-6-deoxy-6-pyrrolidine-beta-cyclodextrin chloride (pyCDCl), mono-6-deoxy-6-(N-methyl-pyrrolidine)-beta-cyclodextrin chloride (N-CH(3)-pyCDCl), mono-6-deoxy-6-(N-(2-hydroxyethyl)-pyrrolidine)-beta-cyclodextrin chloride (N-EtOH-pyCDCl), mono-6-deoxy-6-(2-hydroxymethyl-pyrrolidine)-beta-cyclodextrin chloride (2-MeOH-pyCDCl) were synthesized and used as chiral selectors in capillary electrophoresis for the enantioseparation of carboxylic and hydroxycarboxylic acids and dansyl amino acids. The unsubstituted pyCDCl exhibited the greatest resolving ability. Most analytes were resolved over a wide range of pH from 6.

Enantioselectively controlled release of chiral drug (metoprolol) using chiral mesoporous silica materials.

Chiral porous materials have attracted burgeoning attention on account of their potential applications in many areas, such as enantioseparation, chiral catalysis, chemical sensors and drug delivery. In this report, chiral mesoporous silica (CMS) materials with various pore sizes and structures were prepared using conventional achiral templates (other than chiral surfactant) and a chiral cobalt complex as co-template. The synthesized CMS materials were characterized by x-ray diffraction, nitrogen physisorption, scanning electron microscope and transmission electron microscope.

Monodispersed submicron porous silica particles functionalized with CD derivatives for chiral CEC.

Rapid and efficient enantioseparation of halogen aryl alcohols and beta-blockers propranolol and pindolol in packed bed CEC (p-CEC) using as-prepared submicron porous silica chiral stationary phases (CSPs) has been achieved. Monodispersed 0.66 and 0.

Synthesis of large pore-diameter SBA-15 mesostructured spherical silica and its application in ultra-high-performance liquid chromatography.

A modified synthesis approach for spherical large pore-diameter SBA-15 mesoporous silica (SLP-SBA-15) with particle size range of 0.5-1microm was being reported. It was worth mentioning that in this improved methodology, the use of cetyltrimethylammonium bromide (CTAB) as co-template significantly reduced the self-assembly time from 24h to 45min.

A novel strategy for rapid real-time chiral discrimination of enantiomers using serum albumin functionalized QCM biosensor.

A novel and effective method has been developed for chiral discrimination using a quartz crystal microbalance (QCM) biosensor with self-assembled bovine serum albumin (BSA) or human serum albumin (HSA). The successfully constructed QCM chiral biosensors exhibited rapid and real-time enantioselective recognition. The QCM chiral discrimination factor (alpha(QCM)) can be calculated through resonance frequency shifts in response to five pairs of enantiomers.

Enantioseparation of a novel "click" chemistry derived native beta-cyclodextrin chiral stationary phase for high-performance liquid chromatography.

A novel native beta-cyclodextrin chiral stationary phase was prepared via "click" chemistry with cuprous iodide-triphenylphosphine complex as the catalyst and applied for enantioseparation of Dns-amino acids, substituted phenyl and phenoxy group modified propionic acids, flavonoids, and some pharmaceutical compounds such as nimodipine, propranolol, brompheniramine and bendroflumethiazide in reversed-phase high-performance liquid chromatography. The studied analytes could be resolved under different separation conditions. The resolution of Dns-DL-Leu could reach 5.