Cyclodextrin stationary phase liquid chromatography

Cline-Love, L. and Arunyanart, M., Cyclodextrin mobile-phase and stationary-phase liquid chromatography, ACS Symp. Ser., 297, 226, 1986. 

Cyclodextrin Mobile-Phase and Stationary-Phase Liquid Chromatography... 

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). 

A M. Stalcup, S. Chang, D.W. Armstrong and J. Pitha, (S)-2-Hydroxypropyl-(3-cyclodextrin, A New Chiral Stationary Phase for Reversed-Phase Liquid Chromatography, J. Chromatogr., 513(1990) 181. 

J. Florance and Z. Konteatis, Chiral High-performance Liquid Chromatography of Aromatic Cyclic Dipeptides Using Cyclodextrin Stationary Phases, /. Chromatogr., 543(1991)299. 

A. Malik and K. Jinno, Microcolumn Liquid Chromatography of Polycyclic Aromatic Hydrocarbons and Some Isomeric Compounds on Cyclodextrin Stationary Phases, /. High Resol. Chromatogr. CC, 14(1991)117. 

Source From P-Cyclodextrin as a stationary phase for the group separation of polycyclic aromatic compounds in normal-phase liquid chromatography, in J. Chromatogr. 

Stalcup AM, Chang SC, Armstrong DW, Pitha J (1990) (5)-2-Hydioxypropyl-P-cyclodextrin, a new stationary phase for reversed-phase liquid chromatography. J Chromatogr 513 181-194... 

A. M. Stalcup, Cyclodextrin bonded chiral stationary phases in enantiomer separations in A practical approach to chiral separations by liquid chromatography, G. Subramanian, VCH, Weinheim (1994) Chapter 5. 

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. 

Pihlainen, K. and Kostiainen, R., Effect of the eluent on enantiomer separation of controlled drugs by liquid chromatography-ultraviolet absorbance detection-electrospray ionisation tandem mass spectrometry using vancomycin and native fi-cyclodextrin chiral stationary phases, J. Chromatogr. A, 1033, 91, 2004. 

CR Mitchell, DW Armstrong. Cyclodextrin-based chiral stationary phases for liquid chromatography A twenty-year overview. In G Gubitz, MG Schmid (Eds.) Chiral Separations, Methods and Protocols, Humana Press Inc., Totowa, NJ Humana Press Inc. 61 pp., 2003. 

Berthod, A., He, L., and Armstrong, D.W., Ionic liquids as stationary phase solvents for methylated cyclodextrins in gas chromatography, Chromatographia, 53, 63-68, 2001. 

AM Rizzi, S Cladrowa-Runge, H Jonsson, S Osla. Enantiomeric resolution of derivatized DL-amino acids by high-performance liquid chromatography using /3-cyclodextrin chiral stationary phase a comparison between derivatization labels. J Chromatogr A 710 287-295, 1995. 

Analytically, the inclusion phenomenon has been used in chromatography both for the separation of ions and molecules, in liquid and gas phase (1,79,170,171). Peralkylated cyclodextrins enjoy high popularity as the active component of hplc and gc stationary phases efficient in the optical separation of chiral compounds (57,172). Chromatographic isotope separations have also been shown to occur with the help of Werner clathrates and crown complexes (79,173). 

In view of the importance of chiral resolution and the efficiency of liquid chromatographic methods, attempts are made to explain the art of chiral resolution by means of liquid chromatography. This book consists of an introduction followed by Chapters 2 to 8, which discuss resolution chiral stationary phases based on polysaccharides, cyclodextrins, macrocyclic glyco-peptide antibiotics, Pirkle types, proteins, ligand exchangers, and crown ethers. The applications of other miscellaneous types of CSP are covered in Chapter 9. However, the use of chiral mobile phase additives in the separation of enantiomers is discussed in Chapter 10. 

Stalcup AM, Cyclodextrin bonded chiral stationary phases in enantiomer separations, in A Practical Approach to Chiral Separations by Liquid Chromatography (Subramanian G, Ed.), VCH Verlag, Weinheim, Germany, p. 95 (1994). 

The most popular and commonly used chiral stationary phases (CSPs) are polysaccharides, cyclodextrins, macrocyclic glycopeptide antibiotics, Pirkle types, proteins, ligand exchangers, and crown ether based. The art of the chiral resolution on these CSPs has been discussed in detail in Chapters 2-8, respectively. Apart from these CSPs, the chiral resolutions of some racemic compounds have also been reported on other CSPs containing different chiral molecules and polymers. These other types of CSP are based on the use of chiral molecules such as alkaloids, amides, amines, acids, and synthetic polymers. These CSPs have proved to be very useful for the chiral resolutions due to some specific requirements. Moreover, the chiral resolution can be predicted on the CSPs obtained by the molecular imprinted techniques. The chiral resolution on these miscellaneous CSPs using liquid chromatography is discussed in this chapter. 

The chiral recognition mechanisms in NLC and NCE devices are similar to conventional liquid chromatography and capillary electrophoresis with chiral mobile phase additives. It is important to note here that, to date, no chiral stationary phase has been developed in microfluidic devices. As discussed above polysaccharides, cyclodextrins, macrocyclic glycopeptide antibiotics, proteins, crown ethers, ligand exchangers, and Pirkle s type molecules are the most commonly used chiral selectors. These compounds... 

Mitchell, C. and Armstrong, D. (2004) Cyclodextrin-based Chiral Stationary Phases for Liquid Chromatography A Twenty-year Review, Meth. Molecular Bio. 243,61-112. 

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). 

The preparative-scale separation of enantiomers on chiral stationary phases (CSPs) by GC cannot match the overwhelming success achieved in the realm of liquid chromatography (LC) (Francotte, 1994, 1996 and 2001). Modern commercial instrumentation for preparative-scale GC is not readily available. In contrast to LC, separation factors a in enantioselective GC are usually small (a = 1.01 - 1.20). This is beneficial for fast analytical separations but detrimental to preparative-scale separations. Only in rare instances are large chiral separation factors (a > 1.5) observed in enantioselective GC. Only in one instance, a separation factor as high as a = 10 was detected in enantioselective GC for a chiral fluorinated diether and a modified 7-cyclodextrin (Schurig and Schmidt, 2003) (vide supra). 

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. 

Fujimura, K., Ueda, T., and Ando, T., Retention behavior of some aromatic compounds on chemically bonded cyclodextrin silica stationary phase in liquid chromatography, Anal. Chem., 55, 446, 1983. 

H. Weems and K. Zamani, Resolution of terfenadine enantiomers by j3-cyclodextrin chiral stationary phase high-performance liquid chromatography, Chirality, 4 268 (1992). 

Enormous advances and growth in the use of ordered media (that is, surfactant normal and reversed micelles, surfactant vesicles, and cyclodextrins) have occurred in the past decade, particularly in their chromatographic applications. New techniques developed in this field include micellar liquid chromatography, micellar-enhanced ultrafiltration, micellar electrokinetic capillary chromatography, and extraction of bioproducts with reversed micelles techniques previously developed include cyclodextrins as stationary and mobile-phase components in chromatography. The symposium upon which this book was based was the first major symposium devoted to this topic and was organized to present the current state of the art in this rapidly expanding field. 

In Gas-Liquid Chromatography (GLC), the cyclodextrin (11, 15-18) (dissolved in appropriate solvent) or cyclodextrin derivatives, acetylated (19-21) or methylated (10) were found in some cases to function as highly effective and specific stationary phases. The 6-cyclodextrin polymers were shown to be inadequate (22) or of limited utility (23) for such purposes. 

In high performance liquid chromatography (HPLC), the cyclodextrins (12, 27-36) or highly soluble methylated cyclodextrins (37) in the mobile phase, as well as the silica bonded cyclodextrins (38-40) as stationary phase have attained spectacular success. A series of rapid, elegant separations have been published. The field of application of this method seems to be inexhaustible. 

The use of cyclodextrins as the mobile phase components which impart stereoselectivity to reversed phase high performance liquid chromatography (RP-HPLC) systems are surveyed. The exemplary separations of structural and geometrical isomers are presented as well as the resolution of some enantiomeric compounds. A simplified scheme of the separation process occurring in RP-HPLC system modified by cyclodextrin is discussed and equations which relate the capacity factors of solutes to cyclodextrin concentration are given. The results are considered in the light of two phenomena influencing separation processes adsorption of inclusion complexes on stationary phase and complexation of solutes in the bulk mobile phase solution. 

The classical types of interactions that play a role in separation using conventional polar and nonpolar stationary phases yield limited possibilities for separation of isomers with similar properties. For a solution of this problem, a high degree of selectivity in the separation process is required. It has been shows that these requirements are met by both cyclodextrins and liquid crystals, used as stationary phases in gas chromatography. 

Y. Gong, Y. Xiang, B. Yue, G. Xue, J. S. Bradshaw, H. K. Lee, and M. L. Lee, Application of diaza-18-crown-6-capped (l-cyclodextrin bonded silica particles as chiral stationary phases for ultrahigh pressure capillary liquid chromatography, J. Chromatogr. A 1002 (2003), 63-70. 

The use of chiral stationary phases (CSP) in liquid chromatography continues to grow at an impressive rate. These CSPs contain natural materials such as cellulose and starch as well as totally synthetic materials, utilizing enantioselective and retentive mechanisms ranging from inclusion complexation to Ti-electron interactions. The major structural features found in chiral stationary phases include cellulose, starch, cyclodextrins, synthetic polymers, proteins, crown ethers, metal complexes, and aromatic w-electron systems. 

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