Cyclodextrins bonded stationary phases

FEURLE, J., JOMAA, H., WILHELM, M GUTSCHE, W.B., HERDRICH, M., Analysis of phosphorylated carbohydrates by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry utilising p-cyclodextrin bonded stationary phase, J. Chromatogr., 1998,803,111-119. 

The separation of enantiomers can be effected either by transforming them into diastereoisomers using a chiral reagent and separating them on conventional phases or by separating the enantiomers on chiral phases. The utilization of chiral phases has not yet become routine, but studies of enantiomeric dipeptides have been carried out (115,116). Pirkle et al. (117) and Hyun et al. (118) separated enantiomeric di- and tripeptides (methyl esters of /V-3-5-dinitrobenzoyl derivatives) on chiral stationary phases (CSPs) derived from (R)-a-arylalkylamines, (S)-N-(2-naphthyl) valine, or (S)-1 -(6,7-dimethyl-1 -naphthyl) isobutylamine. These workers were able to separate four peaks for each dipeptide derivative, corresponding to the two enantiomeric pairs (R,R)/(S,S) and (R,S)/(S,R). Cyclodextrin-bonded stationary phases and chiral stationary immobilized a-chymotrypsin phases were used to separate enantiomeric peptides (118a,b). 

Krause M and Galensa R, High-performance liquid chromatography of diastereo-meric flavavone glycosides in Citrus on a P-cyclodextrin-bonded stationary phase (Cyclobond I). J Chromatogr 588 41 15 (1991). 

Feitsma, K., Bosman, J., Drenth, B., and DeZeeuw, R., A study of the separation of enantiomers of some aromatic carboxylic acids by high-performance liquid chromatography on a P-cyclodextrin-bonded stationary phase, J. Chromatogr., 333, 59, 1985. 

Piperaki, S. Parissi-Poulou, M. Koupparis, M. A separation study of tricyclic antidepressant drugs by HPLC with p-cyclodextrin bonded stationary phase. J.Liq.Chromatogr, 1993, 16, 3487-3508 [simultaneous chloripramine, doxepin, imipramine, maprotiline, nortriptyline, protriptyline]... 

Typically plots of In k versus methanol content of the mobile phase is shown in Figure 8. The plots are linear, and exhibit a high degree of correlation based on the respective regression analysis given in Table V. These data indicate that the capacity factor of these test solutes on nonpolar C-18 and cyclodextrin-bonded stationary phases decrease exponentially with the methanol content of the mobile phase. Therefore, the elution behavior obtained with these three types of columns can be explained in a similar manner, and the CD columns behave in the same fashion as conventional reversed phase columns. 

Araki, T., Chiba, M., Tsunoi, S., and Tanaka, M., Separation of chlorophenols by HPLC and capillary electrochromatography using -cyclodextrin-bonded stationary phases. Ana/. ScL, 16, 412, 2000. 

Araki, T, Y Kashiwamoto, S Tsunoi, M Tanaka (1999). Preparation and enantiomer separation behavior of selectively methylated y-cyclodextrin-bonded stationary phases for high-performance liquid chromatography. Journal of Chromatography A, 845( 1-2), 455 62. 

Ryu, JW, HS Chang, YK Ko, JC Woo, DW Koo and DW Kim (1999). Direct chiral separation of tryptophan analogues using heptakis(3-0-Methyl)-beta-cyclodextrin-bonded stationary phase in reversed-phase liquid chromatography. Microchemical Journal, 63(1). 

Li, S and WC Purdy (1991). Liquid chromatographic separation of the enantiomers of dinitrophenyl amino acids using a j8-cyclodextrin-bonded stationary phase. Journal of Chromatography, 543,105-112. 

D.W. Armstrong, W. DeMond, A. Alak, W.L. Hinze, T.E. Riehl and T. Ward, Liquid Chromatographic Separation of Enantiomers Using a Chiral P-Cyclodextrin-Bonded Stationary Phase and Conventional Aqueous-Organic Mobile Phases, Anal. Chem., 57(1985)237. 

P. Macaudiere, M. Caude, R. Rosset and A. Tambute, Resolution or Racemic Amides and Phosphine Oxides on a P-Cyclodextrin-Bonded Stationary Phase by Subcritical Fluid Chromatography, J. Chromatogr., 405(1987)135. 

R. Pereira-Rosario, S. El-Gizaway, J.H. Perrin and C.M. Riley, Analysis of Nasal Solutions Containing Phenylephrine Hydrochloride and Pheniramine Maleate by High Performance Liquid Chromatography on a Cyclodextrin Bonded Stationary Phase and Diode Array Spectrophotometry, Drug Dev. Ind. Pharm., 12(14)(1986)2443. 

H.Y. Aboul-Enein, MR. Islam and S.A. Bakr, Direct HPLC Resolution of Racemic Nomifensine Hydrogen Maleate Using a Chiral Beta-Cyclodextrin-Bonded Stationary Phase, J. Liq. Chromatogr., 11 (7)(1988)1485. 

H.J. Issaq, The Multimodal Cyclodextrin Bonded Stationary Phases for High Performance Liquid Chromatography,/. Liq. Chromatogr., 11(9 10)(1988)2131. 

D.W. Armstrong, C D. Chang and S.H. Lee, (R)- and (S)-Naphthylethyl-carbamate-Substituted P-cyclodextrin Bonded Stationary Phases for the Reversed-Phase Liquid Chromatographic Separation of Enantiomers, J. Chromatogr., 539(1991)83. 

S. Li and W.C. Purdy, Liquid Chromatographic Separation of the Enantiomers of Dinitrophenyl Amino Acids Using a P-Cyclodextrin-bonded Stationary Phase, /. Chromatogr., 543(1991)105. 

M. Krause and R. Galensa, High-performance Liquid Chromatography of Diastereometric Flavanone Glycosides in Citrus on a 13-cyclodextrin-bonded Stationary Phase (CYCLOBOND I), J. Chromatogr., 588(1991)41. 

F. Tazerouti, A. Y. Badjah-Hadj-Ahmed, B. Y. Meklati, F. Pilar and C. Minguillon, Enantiomeric separation of drugs and herbicides on a p-cyclodextrin-bonded stationary phase. Chirality, 2002, 14, 59-66. 

Hinze WI, Riehl TE, Armstrong DW, DeMond W, Alak A, Ward T. Liquid chromatographic separation of enantiomers using a chiral P-cyclodextrin-bonded stationary phase and conventional aqueous-organic mobile phases. Anal Chem 1985 57 237—42. 

Zhong Q, He L, Beesley TE, Trahanovsky WS, Sun P, Wang C, Armstrong DW (2006) Optimization of 2,6-dinitro-4-trifluoromethylphenyl ether substituted cyclodextrin bonded stationary phases for HPLC separation of enantiomers. Chromatographia 64 147-155... 

Macaudiere P, Caude M, Rosset R, Tambute A (1987) Chiral resolution of racemic amides and phosphine oxides on a P-cyclodextrin-bonded stationary phases by super critical fluid chromatography. J Chromatogr 405 135-143... 

---