Chiral resolution by β-cyclodextrin polymer-impregnated ceramic membranes

Journal of Membrane Science

Volumn 164, Issue 1-2, 2000, Pages 177-185

  Krieg, H M ^a   Breytenbach, J C ^a   Keizer, K ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

cyclodextrin polymerisation; Ceramic membrane; Chiral separation; Chlorthalidone; Impregnation

Indexed keywords

ADSORPTION; CERAMIC MATERIALS; DRUG PRODUCTS; IMPREGNATION; ORGANIC POLYMERS; POLYMERIZATION; POROSITY;

BETA CYCLODEXTRIN; CERAMIC MEMBRANES; CHIRAL SELECTIVE MEMBRANES;

PERMSELECTIVE MEMBRANES;

BETA CYCLODEXTRIN DERIVATIVE; CHLORTALIDONE; POLYMER;

ADSORPTION; ARTICLE; CERAMICS; CHEMICAL MODIFICATION; CHIRALITY; COMPLEX FORMATION; DIFFUSION COEFFICIENT; DRUG ISOLATION; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID MEMBRANE; MEMBRANE PERMEABILITY; POLYMERIZATION; PRIORITY JOURNAL;

EID: 0033992109     PISSN: 03767388     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0376-7388(99)00207-0     Document Type: Article

References (21)

1. Pasteur L. Recherches sur les relations qui peuvent existerentre la forme cristalline, la composition chimique et le sens de la polarisation rotatoire. Ann. Chim. Phys. 24:1848;442-459.
2. J. Crosby, Chirality in industry - An overview, in: A.N. Collins, G.N. Sheldrake, J. Crosby (Eds.), Chirality in Industry. The Commercial Manufacture and Applications of Optically Active Compounds, Wiley, Chichester, 1992, pp. 1-66.
3. Wainer I.W., Alembik M.C. The enantiomeric resolution of biologically active molecules on commercially available liquid chromatographic chiral stationary phases. J. Chromatogr. Sci. 40:1988;355-385.
4. E.J. Ariëns, Racemic therapeutics - Problems all along the line, in: C. Brown (Ed.), Chirality in Drug Design and Synthesis, Academic Press, San Diego, 1990, pp. 29-43.
5. F. Jamali, Stereochemically pure drugs: An overview, in: I.W. Wainer (Ed.), Drug Stereochemistry, Marcel Dekker, New York, 1993, pp. 375-384.
6. Francotte E. Contribution of preparative chromatographic resolution to the investigation of chiral phenomena. J. Chromatogr. A. 666:1994;565-601.
7. Keurentjes J.T.F., Nabuurs L.J.W.M., Vegter E.A. Liquid membrane technology for the separation of racemic mixtures. J. Membr. Sci. 113:1996;351-360.
8. Aoki T., Shinohara K., Kaneko T., Oikawa E. Enantioselective permeation of various racemates through an optically active poly{1-[dimethyl(10-pinanyl)silyl]-1-propyne} membrane. Macromolecules. 29:1996;4192-4198.
9. J.T.F. Keurentjes, F.J.M. Voermans, Membrane separations in the production of optically pure compounds, in: A.N. Collins, G.N. Sheldrake, J. Crosby (Eds.), Chirality in Industry II. Developments in the Commercial Manufacture and Applications of Optically Active Compounds, Wiley, Chichester, 1997, pp. 157-182.
10. Keurentjes J.T.F., Linders L.J.M., Beverloo W.A., Van't Riet K. Membrane cascades for the separation of binary mixtures. Chem. Eng. Sci. 47:1992;1561-1568.
11. Yamaguchi T., Nishiura K., Shinbo T., Sugiura M. Enantiomer resolution of amino acids by a polymer-supported liquid membrane containing a chiral crown ether. Chem. Let. 1985:1985;1549-1552.
12. Way J.D., Noble R.D., Flynn T.M., Sloan E.D. Liquid membrane transport: A survey. J. Membr. Sci. 12:1982;239-259.
13. C.A. Koval, Z.E. Reyes, Chemical aspects of facilitated transport through liquid membranes, in: R.D. Noble, J.D. Way (Eds.), Liquid Membranes. Theory and Application, American Chemical Society, Washington, DC, 1987, pp. 28-38.
14. Masawaki T., Sasai M., Tone S. Optical resolution of an amino acid by an enantioselective ultrafiltration membrane. J. Chem. Eng. Japan. 25:1992;33-38.
15. Heard C.M., Suedee R. Stereoselective adsorption and trans-membrane transfer of propranolol enantiomers using cellulose derivatives. Int. J.Pharmaceutics. 139:1996;15-23.
16. H.M. Krieg, J.C. Breytenbach, V.M. Linkov, S. Kuhl, Ceramic based membranes, the preparation and use thereof, S. A. Patent 98/7716, 1998.
17. Hoffman J.L. Chromatography of nucleic acids on cross-linked cyclodextrin gels having inclusion-forming capacity. J. Macromolecular Sci. Chem. A7:1973;1147-1157.
18. Wiedenhof N., Lammers J.N.J.J., Van Panthaleon Van Eck C.L. Properties of cyclodextrins. Part III. Cyclodextrin-epichlorohydrin resins: preparation and analysis. Die Stärke. 5:1969;119-122.
19. J.G.A. Bitter, Basic diffusion equation, in: J.G.A. Bitter (Ed.), Transport Mechanism in Membrane Separation Processes, New York, Plenum Press, 1991, pp. 31-37.
20. Rizzi A.M., Plank C. Coupled column chromatography in chiral separations: Systems employing (-cyclodextrin phases for chiral separation. J. Chromatogr. 557:1991;199-213.
21. L. Jicsinski, É. Fenyvesi, H. Hashimoto, A. Ueno, Cyclodextrin derivatives, in: J.L. Atwood, J.E.D. Davies, D.D. MacNicol, F. Vögtle (Eds.), Comprehensive Supramolecular Chemistry, vol 3, Cyclodextrins, Elsevier, New York, 1996, pp. 57-174.