A cationic cyclodextrin clicked bilayer chiral stationary phase for versatile chiral separation in HPLC

A cationic cyclodextrin (CD) clicked bilayer chiral stationary phase (CSP) was developed via click chemistry for chiral separations in multimode high-performance chromatography (HPLC). The versatility of this new CSP was evaluated using 17 model racemic pairs including aromatic alcohols, flavonoids and isoxazoline enantiomers in both reversed-phase (RP) and normal-phase (NP) HPLC. The CD functionality-enhanced chiral selectivity was elucidated in different elution modes. Higher chiral resolutions were shown in the RP-elution mode due to the inclusion complexation in comparison to the NP-elution mode. The highest chiral resolution of 4.40 was achieved for 4ClPh-OPr, with 12 racemic pairs baseline separated in RP-HPLC. The addition of organic modifiers in mobile phases plays an important role in optimizing the enantioselectivities of the cationic CD bilayer CSP in NP-HPLC.

[1]  Yan Liu,et al.  Chiral 3D Covalent Organic Frameworks for High Performance Liquid Chromatographic Enantioseparation. , 2018, Journal of the American Chemical Society.

[2]  Lijun Ruan,et al.  A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography , 2018, Electrophoresis.

[3]  C. Zhigang,et al.  Preparation and evaluation of a novel N-benzyl-phenethylamino-β-cyclodextrin-bonded chiral stationary phase for HPLC , 2017 .

[4]  Yong Wang,et al.  Enantioseparation of Flavanoids, Isoxazolines, Dansyl Amino Acids and β‐Blockers on Native and Phenylcarbamoylated α, β and γ‐Cyclodextrin Chiral Stationary Phases , 2017 .

[5]  Katsuhiro Maeda,et al.  Chiral stationary phases consisting of π-conjugated polymers bearing glucose-linked biphenyl units: reversible switching of resolution abilities based on a coil-to-helix transition , 2017 .

[6]  Pavel Jandera,et al.  Recent advances in stationary phases and understanding of retention in hydrophilic interaction chromatography. A review. , 2017, Analytica chimica acta.

[7]  Weihua Tang,et al.  Enantioseparation of isoxazolines with functionalized perphenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC , 2017, Electrophoresis.

[8]  E. Tesařová,et al.  Cyclic Oligosaccharide-Based Chiral Stationary Phases Applicable to Drug Purity Control; A Review. , 2017, Current Medicinal Chemistry.

[9]  T. Farkas,et al.  Effect of pore-size optimization on the performance of polysaccharide-based superficially porous chiral stationary phases for the separation of enantiomers in high-performance liquid chromatography. , 2017, Journal of chromatography. A.

[10]  Weihua Tang,et al.  Cationic cyclodextrin clicked chiral stationary phase for versatile enantioseparations in high-performance liquid chromatography. , 2016, Journal of chromatography. A.

[11]  F. Gasparrini,et al.  Pirkle-type chiral stationary phase on core-shell and fully porous particles: Are superficially porous particles always the better choice toward ultrafast high-performance enantioseparations? , 2016, Journal of chromatography. A.

[12]  Weihua Tang,et al.  Engineering Cyclodextrin Clicked Chiral Stationary Phase for High-Efficiency Enantiomer Separation , 2015, Scientific Reports.

[13]  Weihua Tang,et al.  Clicked AC regioisomer cationic cyclodextrins for enantioseparation , 2014 .

[14]  Weihua Tang,et al.  Evaluation of perphenylcarbamated cyclodextrin clicked chiral stationary phase for enantioseparations in reversed phase high performance liquid chromatography. , 2014, Journal of chromatography. A.

[15]  T. Tan,et al.  Surface-up constructed tandem-inverted bilayer cyclodextrins for enhanced enantioseparation and adsorption. , 2014, Journal of chromatography. A.

[16]  O. Werz,et al.  Chromatographic separation and biological evaluation of benzimidazole derivative enantiomers as inhibitors of leukotriene biosynthesis. , 2014, Journal of Pharmaceutical and Biomedical Analysis.

[17]  T. Tan,et al.  Thiol-ene click chemistry derived cationic cyclodextrin chiral stationary phase and its enhanced separation performance in liquid chromatography. , 2014, Journal of chromatography. A.

[18]  Bo Tang,et al.  High-performance liquid chromatographic enantioseparation of racemic drugs based on homochiral metal-organic framework. , 2014, Analytical chemistry.

[19]  C. Amatore,et al.  NHC-capped cyclodextrins (ICyDs): insulated metal complexes, commutable multicoordination sphere, and cavity-dependent catalysis. , 2013, Angewandte Chemie.

[20]  Weihua Tang,et al.  A family of single‐isomer, dicationic cyclodextrin chiral selectors for capillary electrophoresis: Mono‐6A‐ammonium‐6C‐butylimidazolium‐β‐cyclodextrin chlorides , 2013, Electrophoresis.

[21]  Yong Wang,et al.  Recent development of cyclodextrin chiral stationary phases and their applications in chromatography. , 2012, Journal of chromatography. A.

[22]  Tang Weihua,et al.  Recent advances in pharmaceutical separations with supercritical fluid chromatography using chiral stationary phases , 2012 .

[23]  Weihua Tang,et al.  Cationic cyclodextrins chemically-bonded chiral stationary phases for high-performance liquid chromatography. , 2012, Analytica chimica acta.

[24]  Weihua Tang,et al.  Novel β-cyclodextrin chiral stationary phases with different length spacers for normal-phase high performance liquid chromatography enantioseparation. , 2011, Journal of chromatography. A.

[25]  Renhua Liu,et al.  Application of click chemistry on preparation of separation materials for liquid chromatography. , 2011, Chemical Society reviews.

[26]  M. Lämmerhofer Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. , 2010, Journal of chromatography. A.

[27]  C. Ching,et al.  Enantiomer separation of flavour and fragrance compounds by liquid chromatography using novel urea-covalent bonded methylated beta-cyclodextrins on silica. , 2002, Journal of chromatography. A.

[28]  S. Bocian,et al.  Amino acids, peptides, and proteins as chemically bonded stationary phases--A review. , 2016, Journal of separation science.

[29]  S. Ng,et al.  Modified Cyclodextrins for Chiral Separation , 2013 .

[30]  V. T. D'Souza,et al.  A convenient method for functionalization of the 2-position of cyclodextrins , 1990 .