Chromatography on cyclodextrin

Vigh, G., Quintero, G., and Farkas, G. (1989) Displacement chromatography on cyclodextrin-silicas. 1. Separation of positional and geometrical isomers in the reversed-phase mode. J. Chromatogr. 484,237—250. 

J. T. Anderson and G. Kaiser, Elution Order in Liquid Chromatography on Cyclodextrin Phases. Dependence on the Amount of Organic Modifier in the Eluent, Fresenius Z. Anal. Chem., 749(1989). 

G. Vigh, G. Quintero and G. Farkas, Displacement Chromatography on Cyclodextrin- Silicas. I. Separation of Positional and Geometrical Isomers n the Reversed Phase Mode, J. Chromatogr., 484 (1989)237. 

G. Farkas, L.H. Irgens, G. Quintero, M.D. Beeson, A. Al-Saeed and G. Vigh, Displacement Chromatography on Cyclodextrin Silicas, IV. Separation of the Enantiomers of Ibuprofen, J. 

Gas chromatography (GC) has also been used for preparative purposes, but is restricted to relatively volatile racemates such as anesthetics, pheromones or monoterpenes and, therefore, very few applications are reported. Nevertheless, in the cases to which GC may be applied, it could be considered as an economical alternative to HPLC. Most of the resolutions of enantiomers were performed on cyclodextrin-derived CSPs [109, 144-153], and only on very few occasions were other chiral selectors used [153]. 

Capillary gas chromatography on optically active modified cyclodextrin phases is a simple, fast, accurate and highly sensitive method for the enantiomeric analysis of chiral volatile compounds. 

The extracts contained almost pure pheromone, with only minor amounts of other components. By comparison with synthetic samples, derivatization, and gas chromatography on a chiral cyclodextrin phase, the pheromone was identified as a 95 5 mixture of (5)- and (/ )-enantiomers of dimethyl citrate (cupilure (3), Fig. 4.2). Only the (5)-enantiomer was active (Tichy et al., 2001). Cupilure is probably present in ionized form on the silk (pK 3.5), because solvent extracts were neutral. The ionized carboxyl group may be conjugated to basic amino acids of the silk proteins. This would also explain why the pheromone is not volatile, despite its relatively low molecular weight, and is easily washed from the silk by water, including rain. In the tropical habitat of C. salei this would ensure the presence of cupilure only on freshly laid silk. 

The purity of the ethyl glycidate prepared according to this procedure was >97% as measured by gas chromatography (BP5 capillary column from SGE). The enantiomeric purity was greater than 99% ee as determined by chiral gas chromatography on a 50-m CYDEX-B capillary column (0-cyclodextrin stationary... 

TABLE 11 The Enantiomeric Resolution of Racemic Compounds on Cyclodextrin-Based CSPs by Means of Subcritical and Supercritical Fluid Chromatography... 

Adsorption chromatography on cellulose was examined for azo dyes that form complexes with CDs using aqueous solutions of a-CD as eluents. The cyclodextrin substantially increases the RF values [61], Commercial a-, [>-. and y-CD polymers were used for the same purpose, however changes of RF were observed only for some azo dyes [62], 2-Hydroxypropyl-P-cyclodextrin used in 10-20% concentration causes complete elution of many compounds [63],... 

Huynh, T.K.X. Lederer, M. and Leipzig-Pagani, E. (1995) Adsorption chromatography on cellulose XII. General effects of aqueous solutions of a-cyclodextrin as eluent, J. Chromatogr. 695, 155-159. 

Lederer, M. and Nguyen, H.K.H. (1996) Adsorption chromatography on cellulose XIV. Some results using aqueous solutions of soluble cyclodextrin polymers as eluents, J. Chromatogr. 723, 405-409. 

Juza, M, Braun, M., and Schurig, V. (1997) Preparative enantiomer separation of the chiral inhalation anesthetics enfiurane, isoflurane and desflurane by gas chromatography on a derivatized 7-cyclodextrin stationary phase, J. Chromatogr. A 769, 119-127. 

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. 

M. Jung and V. Schurig, Extending the scope of enantiomer separation by capillary supercritical fluid chromatography on immobilized polysiloxane anchored permethyl-B-cyclodextrin (Chirasil-Dex), J. High Resolut. Chromstogr., 76 215 (1993). 

Tripathi AM, Mhalas JG, Rama-Rao NV. 1989. Determination of 2,6 and 4,6-Dinitrocresols by high performance liquid chromatography on a beta-cyclodextrin bonded column. J Chromatogr 466 442-445. 

The study of the chromatographic behavior of natural indole alkaloids on cyclodextrin polymers was different, and unexpectedly high retentions were observed in mildly acidic buffer solutions at room temperature, which permitted their separation by inclusion chromatography (25) (Table IV). Figure 7 shows the separation of two Vinca-alkaloids of very similar structure, the (+)-vincamine and (+)-apovincamine. 

Figure 8 shows the analytical base-line separation of quebrachamine antipodes by inclusion chromatography on B-cyclodextrin polymers. 

Vetter, W. Schurig, V, Enantioselective determination of chiral organochlorine compounds in biota by gas chromatography on modified cyclodextrins 7. Chromatogr. A 1997,774,143-175. 

Besides the corresponding epoxy alcohol the enantiomer of the allylic alcohol reacting more slowly was recovered with high e.e. In this case, the ratio of enantiomers was determined similarly to Konig method [24] by gas chromatography on a column with perpentylated oc-cyclodextrine. 

Parkas, G, LH Irgens, G Quintero, MD Beeson, A Al-Saeed and G Vigh (1993). Displacement chromatograpy on cyclodextrin silicas, IV. Separation of the Enantiomers of Ibuprofen. Journal of Chromatography, 645,67-74. 

Shimada, K, T Oe and M Suzuki (1991). Effect of derivatization of steroids on their retention behaviour in inclusion chromatography using cyclodextrin as a mobile phase additive. Journal of Chromatography A, 558(1), 306 331. 

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