A new single‐urea‐bound 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin chiral stationary phase and its enhanced separation performance in normal‐phase liquid chromatography

A new single‐urea‐bound chiral stationary phase based on 3,5‐dimethylphenylcarbamoylated β‐cyclodextrin was prepared through the Staudinger reaction of mono (6A‐azido‐6A‐deoxy)‐per(3,5‐dimethylphenylcarbamoylated) β‐cyclodextrin and 3‐aminopropyl silica gel under CO2 atmosphere. The new phase exhibited good enantioseparation performance for 33 analytes using normal‐phase HPLC conditions; 19 of them were baseline separated. Effects of structure of analytes, alcoholic modifiers, and acidic/basic additives on separation performances of this new cyclodextrin chiral stationary phase have been studied in detail. The results showed that the retention and resolution of acidic and basic analytes on the CSP were greatly affected by the additives. Peak symmetry for some analytes could be improved by simultaneously adding acidic and basic additives to the mobile phase. This work expands the potential applications of the cyclodextrin‐based chiral stationary phases in the normal‐phase HPLC.

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

[2]  P. Peluso,et al.  Recent trends and applications in liquid‐phase chromatography enantioseparation of atropisomers , 2017, Electrophoresis.

[3]  C. Castells,et al.  Chiral separation of aryloxyphenoxy‐propionate herbicides in a permethyl‐β‐cyclodextrin based column. Influence of temperature and mobile phase composition on enantioselectivity , 2017, Electrophoresis.

[4]  Sonia Morante-Zarcero,et al.  Ordered mesoporous silica functionalized with β-cyclodextrin derivative for stereoisomer separation of flavanones and flavanone glycosides by nano-liquid chromatography and capillary electrochromatography. , 2017, Journal of chromatography. A.

[5]  Weihua Tang,et al.  Per(3-chloro-4-methyl)phenylcarbamate cyclodextrin clicked stationary phase for chiral separation in multiple modes high-performance liquid chromatography. , 2016, Analytica chimica acta.

[6]  Zhiming Zhou,et al.  Preparation of chiral oxazolinyl-functionalized β-cyclodextrin-bonded stationary phases and their enantioseparation performance in high-performance liquid chromatography. , 2016, Journal of separation science.

[7]  D. Armstrong,et al.  Advances in high-throughput and high-efficiency chiral liquid chromatographic separations. , 2016, Journal of chromatography. A.

[8]  Yong Wang,et al.  Thioether bridged cationic cyclodextrin stationary phases: Effect of spacer length, selector concentration and rim functionalities on the enantioseparation. , 2016, Journal of chromatography. A.

[9]  Hongxing Dong,et al.  Preparation and chromatographic evaluation of β-cyclodextrin derivative CSPs bearing substituted phenylcarbamate groups for HPLC , 2016 .

[10]  Y. Okamoto,et al.  Efficient Separation of Enantiomers Using Stereoregular Chiral Polymers. , 2016, Chemical reviews.

[11]  S. Ng,et al.  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. , 2015, Journal of separation science.

[12]  N. Davies,et al.  Enantiospecific pharmacokinetics of isoxanthohumol and its metabolite 8-prenylnaringenin in the rat. , 2015, Molecular nutrition & food research.

[13]  Weihua Tang,et al.  Recent development of cationic cyclodextrins for chiral separation , 2015 .

[14]  Jun Fan,et al.  Comparative HPLC enantioseparation on substituted phenylcarbamoylated cyclodextrin chiral stationary phases and mobile phase effects. , 2014, Journal of pharmaceutical and biomedical analysis.

[15]  T. Farkas,et al.  On the effect of basic and acidic additives on the separation of the enantiomers of some basic drugs with polysaccharide-based chiral selectors and polar organic mobile phases. , 2013, Journal of chromatography. A.

[16]  L. Szente,et al.  Cyclodextrins in analytical chemistry: host-guest type molecular recognition. , 2013, Analytical chemistry.

[17]  Sheng-run Zheng,et al.  Synthesis of a novel cyclodextrin-derived chiral stationary phase with multiple urea linkages and enantioseparation toward chiral osmabenzene complex. , 2013, Journal of chromatography. A.

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

[19]  A. Ohnishi,et al.  Complementary enantiorecognition patterns and specific method optimization aspects on immobilized polysaccharide-derived chiral stationary phases. , 2012, Journal of chromatography. A.

[20]  Jun Fan,et al.  The impact of silica gel pore and particle sizes on HPLC column efficiency and resolution for an immobilized, cyclodextrin-based, chiral stationary phase. , 2010, Journal of separation science.

[21]  Weiguang Zhang,et al.  Phenylcarbamoylated beta-CD: pi-acidic and pi-basic chiral selectors for HPLC. , 2010, Journal of separation science.

[22]  Jun Fan,et al.  Preparation and enantioseparation characteristics of a novel chiral stationary phase based on mono (6(A)-azido-6(A)-deoxy)-per(p-chlorophenylcarbamoylated) beta-cyclodextrin. , 2008, Journal of chromatography. A.

[23]  D. Armstrong,et al.  Considerations on HILIC and polar organic solvent-based separations: use of cyclodextrin and macrocyclic glycopetide stationary phases. , 2008, Journal of separation science.

[24]  G. Carter,et al.  Direct high-performance liquid chromatographic separation of the enantiomers of an aromatic amine and four aminoalcohols using polysaccharide chiral stationary phases and acidic additive. , 2007, Chirality.

[25]  S. Ng,et al.  Urea bonded cyclodextrin derivatives onto silica for chiral HPLC. , 2006, Journal of separation science.

[26]  Lingfeng He,et al.  Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography. , 2006, Journal of chromatography. A.

[27]  Rodger W Stringham,et al.  Chiral separation of amines by high-performance liquid chromatography using polysaccharide stationary phases and acidic additives. , 2006, Journal of chromatography. A.

[28]  R. Stringham,et al.  The effect of acidic and basic additives on the enantioseparation of basic drugs using polysaccharide-based chiral stationary phases. , 2006, Chirality.

[29]  D. Armstrong,et al.  Selectivity of a Native β‐Cyclodextrin Column in the Separation of Catechins , 2005 .

[30]  C. Ching,et al.  Preparation and Enantioseparation Properties of Chiral Stationary Phases Derived from Arylcarbamoylated β‐Cyclodextrin , 2005 .

[31]  D. Armstrong,et al.  Cyclodextrin-based chiral stationary phases for liquid chromatography: a twenty-year overview. , 2004, Methods in molecular biology.

[32]  I. Ali,et al.  Studies on the effect of alcohols on the chiral discrimination mechanisms of amylose stationary phase on the enantioseparation of nebivolol by HPLC. , 2001, Journal of biochemical and biophysical methods.

[33]  G. Beecher,et al.  Liquid chromatographic method for the separation and quantification of prominent flavonoid aglycones. , 2000, Journal of chromatography. A.

[34]  C. Ching,et al.  A facile immobilization approach for perfunctionalised cyclodextrin onto silica via the Staudinger reaction , 1999 .

[35]  G. Félix,et al.  Chromatographic properties in normal-mode HPLC of chiral stationary phases based on substituted β-cyclodextrins , 1997 .

[36]  Y. Tang Significance of mobile phase composition in enantioseparation of chiral drugs by HPLC on a cellulose-based chiral stationary phase. , 1996, Chirality.

[37]  Y. Kaida,et al.  Preparation and chromatographic evaluation of 3,5-dimethylphenyl carbamoylated β-cyclodextrin stationary phases for normal-phase high-performance liquid chromatographic separation of enantiomers , 1993 .

[38]  D. Armstrong,et al.  Derivatized cyclodextrins for normal-phase liquid chromatographic separation of enantiomers , 1990 .

[39]  K. Hatada,et al.  Direct Optical Resolution of Carboxylic Acids by Chiral HPLC on Tris(3,5-dimethylphenylcarbamate)s of Cellulose and Amylose , 1988 .

[40]  J. Finn,et al.  Broad spectrum resolution of optical isomers using chiral high-performance liquid chromatographic bonded phases , 1980 .