Chiral Stationary Phases for Preparative Enantioselective Chromatography

Preparative Enantioselective Chromatography

Volumn , Issue , 2007, Pages 48-77

  Francotte, Eric ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

Chiral polymers; Chiral stationary phases (CSPs); Enantioselective chromatography; Ligand exchange chromatography; Polysaccharides

Indexed keywords

EID: 84890704606     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470988428.ch3     Document Type: Chapter

References (157)

1. Francotte, E., "Contribution of preparative chromatographic resolution to the investigation of chiral phenomena", J. Chromatogr. A, 1994, 666, 565-601.
2. Francotte, E., "Preparation of drug enantiomers by chromatographic resolution on chiral stationary phases". In Aboul-Enein, H.Y. and Wainer, I.W. (eds), The Impact of Stereochemistry on Drug Development and Use, Chemical Analysis Series, Vol. 142, John Wiley & Sons; New York, 1997, pp. 633-683.
3. Francotte, E., "Chromatography as a separation tool for the preparative resolution of racemic compounds". In Ahuja, S. (ed.), Chiral Separations: Applications and Technology, American Chemical Society, New York, 1996, pp. 271-308.
4. Francotte, E.R., "Enantioselective chromatography as a powerful alternative for the preparation of drug enantiomers", J. Chromatogr. A, 2001, 906, 379-397.
5. Andersson, S. and Allenmark, S.G., "Preparative chiral chromatographic resolution of enantiomers in drug discovery", J. Biochem. Biophys. Methods, 2002, 54, 11-23.
6. Negawa, M. and Shoji, F., "Optical resolution by simulated moving-bed adsorption technology", J. Chromatogr., 1992, 590, 113-117.
7. Nicoud, R.M., "The simulated moving bed: a powerful chromatographic process", LC-GC Int., 1992, 5, 43-47.
8. Ching, C.B., Lim, B.G., Lee, E.J. and Ng, S.C., "Preparative resolution of praziquantel enantiomers by simulated counter-current chromatography", J. Chromatogr., 1993, 634, 215-219.
9. Schulte, M. and Strube, J., "Preparative enantioseparation by simulated moving bed chromatography", J. Chromatogr. A, 2001, 906, 399-416.
10. Willsẗatter, R., "Quinones", Chem. Ber., 1904, 37, 3758-3759.
11. Henderson, G.M. and Rule, H.G., "A new method of resolving a racemic compound", J. Chem. Soc., 1939, 1568-1573.
12. Lecoq, H., "D́edoublement raćemique par chromatographie"; Bul. Soc. Royal Sci. Liege, 943, 12, 316- 323.
13. Prelog, V. and Wieland, P., "Ü ber die Spaltung der Tröger'schen Base in optische Antipoden, ein Beitrag zur Stereochemie des dreiwertigen Stickstoffs", Helv. Chim. Acta, 1944, 27, 1127-1134.
14. Dent, C.E., "Behavior of sixty amino acids and other ninhydrin-reacting substances on phenol-collidine filter-paper chromatograms, with notes as to the occurrence of some of them in biological fluids", Biochem. J., 1948, 43, 169-180.
15. Kotake, M., Sakan, T., Nakamura, N. and Senoh, S., "Resolution into optical isomers of some amino acids by paper chromatography", J. Am. Chem. Soc., 1951, 73, 2973-2974.
16. Dalgliesh, C.E., "Optical resolution of aromatic amino acids on paper chromatograms", J. Chem. Soc., 1952, 3940-3942.
17. Krebs, H. and Rasche, R., "Ü ber die chromatographische Spaltung von Racematen. I Optisch aktive Kobaltkomplexe von Dithios̈auren", Zeit. Anorg. Chem. Allgem. Chem., 1954, 276, 236-246.
18. Krebs, H., Diewald, J., Arlitt, H. andWagner, J.A., "Ü ber die chromatographische Spaltung von Racematen. II Versuche zur Aktivierung von oktaederf̈ormig gebauten Komplexen", Zeit. Anorg. Chem. Allgem. Chem., 1956, 287, 98-106.
19. Krebs, H., Wagner, J.A. and Diewald, J., "Ü ber die chromatographische Spaltung von Racematen. III Versuche zur Aktivierung organischer Hydroxy- und Aminoverbindungen mit asymmetrischem C-Atom", Chem. Ber., 1956, 89, 1875-1883.
20. Steckelberg, W., Bloch, M. and Musso, H., "Notiz zur Antipodentrennung von Biphenylderivaten durch Chromatographie", Chem. Ber., 1968, 101, 1519-1521.
21. L̈uttringhaus, A. and Peters, K.C., "Konformationelle Isomerie bei einem Derivat des Cyclotriveratrylens", Angew. Chem., 1966, 78, 603.
22. Schl̈ogl, K. and Mechtler, H., "Ein optisch aktives carbodiimid", Angew. Chem., 1966, 78, 606-607.
23. Falk H. and Schl̈ogl, K., "Stereochemie von metallocenen- VII. Eine Beziehung zwischenKonfigurationund Vorzeichnen der Drehung bei optisch aktiven Metallocenen", Tetrahedron, 1966, 22, 3047-3053.
24. Francotte, E. and Junker-Buchheit, A., "Preparative chromatographic separation of enantiomers", J. Chromatogr., 1992, 576, 1-45.
25. Hesse, G. and Hagel, R., "Eine vollsẗandige Racemattrenung durch Elutions-Chromatographie an Cellulosetri-acetat", Chromatographia, 1973, 6, 277-280.
26. Hesse, G. and Hagel, R., "Die chromatographische Racemattrennung", Liebigs Ann. Chem., 1976, 996- 1008.
27. Dingenen, J., "Polysaccharide phases in enantio-separations". In Subramanian, G. (ed.), A Practical Approach to Chiral Separations by Liquid Chromatography; VCH, Weinheim, 1994, Chapt 6.
28. Helfferich, F.G., " 'Ligand exchange': a novel separation technique", Nature, 1961, 189, 1001-1002.
29. Roghozhin, S.V. and Davankov, V.A., "Chromatographic method to separate optical isomers of compounds forming complexes with the ions of transition metals", Ger. Offen. 1 932 190 (Appl. Aug. 1, 1968), 1970.
30. Bernauer, K., "Separation of racemic mixtures by chromatography on an optically active support", Swiss Patent 490 292 (Appl. Mar. 22, 1968), 1970.
31. Jozefonvicz, J., Petit, M.A. and Szubarga, A., "Preparative resolution of DL-proline by liquid chromatography on a polystyrene resin containing the L-proline copper(II) complex", J. Chromatogr., 1978, 147, 177- 183.
32. Davankov, V.A., Zolotarev, Y.A. and Kurganov, A.A., "Ligand-exchange chromatography of racemates, XI: Complete resolution of some chelating racemic compounds and nature of sorption enantioselectivity", J. Liq. Chromatogr., 1979, 2, 1191-1204.
33. Application Guide, JPS Chimie, Bevaix, Switzerland, 1987
34. Davankov, V.A. and Rogozhin, S.V., "Ligand chromatography as a novel method for the investigation of mixed complexes. Stereoselective effects in alpha-amino acid-copper(II) complexes", J. Chromatogr., 1971, 60, 280-283.
35. Blaschke, G. and Donow, F., "Untersuchung chromatographischer Racemattrennungen, IV. Trennwirkung optisch aktiven Poly[N-((S)-1-phenyl̈athyl)acrylamides] in Abḧangigkeit vom Polymerisationsverfahren", Chem. Ber., 1975, 108, 1188-1197.
36. Blaschke, G., Kraft, H.-P. and Markgraf, H., "Racemattrennung des Thalidomids und anderer Glutarimid-Derivate", Chem. Ber., 1980, 113, 2318-2322.
37. Francotte, E.,Wolf, R.M., Lohmann, D. andM̈uller, R., "Chromatographic resolution of racemates on chiral stationary phases. Influence of the supramolecular structure of cellulose triacetate", J. Chromatogr., 1985, 347, 25-37.
38. Ichida, A., Shibata, T., Yuki, Y., Namikoshi, H. and Toga, Y., "Resolution of enantiomers by HPLC on cellulose derivatives", Chromatographia, 1984, 19, 280-284.
39. Pirkle,W.H. and Pochapsky, T.C., "Generation of extreme selectivity in chiral recognition"; J. Chromatogr., 1986, 369, 175-177.
40. Wulff, G. and Sarhan, A., "Use of polymers with enzyme-analogous structures for the resolution of racemates", Angew. Chem. Int. Ed., 1972, 11, 341.
41. Okamoto,Y. andYashima, E., "Polysaccharide derivatives for chromatographic separation of enantiomers", Angew. Chem. Int. Ed., 1998, 37, 1021-1043.
42. Mannschreck, A., Koller, H. andWernicke, R., "Microcrystalline cellulose triacetate, a versatile stationary phase for the separation of enantiomers", Kontakte (Darmstadt), 1985, 40-48.
43. Koller, H., Rimb̈ock, K.-H. and Mannschreck, A., "Liquid chromatography on triacetylcellulose, Part VII: High-pressure liquid chromatography on triacetylcellulose. Characterization of a sorbent for the separation of enantiomers", J. Chromatogr., 1983, 282, 89-94.
44. Rimb̈ock, K.-H., Kastner, F. and Mannschreck, A., "Liquid chromatography on triacetylcellulose, 12: Preparative separation of enantiomers on an axially compressed column" J. Chromatogr., 1985, 329, 307- 310.
45. Rizzi, A.M., "Evaluation of the optimisation potential in high-performance liquid chromatographic separations of optical isomers with swollen microcrystalline cellulose triacetate", J. Chromatogr., 1989, 478, 101-119.
46. Isaksson, R., Erlandsson, P., Hansson, L., Holmberg, A. and Berner, S.J., "Triacetylcellulose as a chiral stationary phase for high-performance liquid chromatography", J. Chromatogr., 1990, 498, 257-280.
47. Wolf, R.M., Francotte, E. and Lohmann, D., "Quantitative correlation between calculated molecular properties and retention of a series of structurally related racemates on cellulose triacetate", J. Chem. Soc. Perkin Trans. 2, 1988, 893-901.
48. Isaksson, R., Wennerstr̈om, H and Wennerstr̈om, O., "Symmetry and chiral recognition: separation of enantiomers on triacetylcellulose columns", Tetrahedron, 44, 1988, 1697-1705.
49. Erlandsson, P., Isaksson, R., Nilsson, I. and Wold, S.J., "Chemometric approach to explain the liquid chromatographic retention of some chiral indoles on swollen microcrystalline triacetylcellulose", J . Chromatogr., 1989, 466, 364-370.
50. Francotte, E. andWolf, R.M., "Preparation of chiral building blocks and auxiliaries by chromatography on cellulose triacetate (CTA I): indications for the presence of multiple interaction sites in CTA I", Chirality, 1990, 2, 16-31.
51. Roussel, C., Stein, J.-L., Beauvais, F. and Chemlal, A., "Example of the concentration dependence of elution order in the resolution of enantiomers on microcrystalline triacetylcellulose chiral stationary phase", J. Chromatogr., 1989, 462, 95-103.
52. Hesse, G. and Hagel, R.," Ü ber Inclusions-Chromatographie und ein neues Retentionsprinzip für Benzolderivate", Chromatographia, 1976, 9, 62-68.
53. Boland, W., Niedermeyer, U., Jaenicke, L. and G̈orisch, H., "Enantioselective Syntheses and absolute configurations of Viriden and Aucantene, two constituents of algae pheromone bouquets", Helv. Chim. Acta, 1985, 68, 2062-2073.
54. Agranat, I., Suissa, M.R., Cohen, S., Isaksson, R., Sandstr̈om, J., Dales, J. and Grace, D., "A novel titaniuminduced aromatic dicarbonyl coupling. Synthesis of a chiral strained polynuclear aromatic hydrocarbon", J. Chem. Soc. Chem. Commun., 1987, 381-383.
55. Lohmann, D., Auer, K. and Francotte, E., "Scale-up in LC separation of bioactive enantiomers on cellulose triacetate". Presentation at the International Symposium on Chromatography, Rehovot, Israel, Nov. 1988.
56. Nicoud, R.-M., Fuchs, G., Adam, P., Bailly, M., K̈usters, E., Antia, F.D., Reuille, R. and Schmid, E., "Preparative scale enantioseparation of a chiral epoxide: comparison of liquid chromatography and simulated moving bed adsorption technology", Chirality, 1993, 5, 267-271.
57. Rimb̈ock, K.-H., Kastner, F. and Mannschreck, A., "Microcrystalline tribenzoylcellulose: a highperformance liquid chromatographic sorbent for the separation of enantiomers", J. Chromatogr., 1986, 351, 346-350.
58. Francotte, E. and Baisch, G., "Preparation and use of finely divided esters of cellulose with aromatic or aromatic-aliphatic carboxylic acids", European Patent, EP 0 316 270 A2 (Priority Oct. 26, 87), 1988.
59. Francotte, E. and Wolf, R.M., "Benzoyl cellulose beads in the pure polymeric form as a new powerful sorbent for the chromatographic resolution of racemates", Chirality, 1991, 3, 43-55.
60. Francotte, E. and Wolf, R.M., "Chromatographic resolution on methylbenzoylcellulose beads. Modulation of the chiral recognition by variation of the position of the methyl group on the aromatic ring", J. Chromatogr., 1992, 595, 63-75.
61. Francotte, E., Lang, R.W. and Winkler, T., "New chiral fluoroanthryl derivatives: resolution of the enantiomers by chromatography on cellulose esters and their evaluation as chiral solvating agents in NMR spectroscopy", Chirality, 1991, 3, 177-182.
62. Drenkard, S., Ferris, J. and Eschenmoser, A., "Chemistry of alpha-aminonitriles, 2: Aziridine-2-carbonitrile: photochemical formation from 2-aminopropenenitrile", Helv. Chim. Acta, 1990, 73, 1373-1390.
63. Francotte, E., "Process for the preparation of aromatic carbamoyl-substituted polysaccharide derivatives", Patent application WO 9627639 (Priority, Mar. 1995), 1996.
64. Francotte, E., "3,5-Dimethylphenylcarbamate of cellulose: a powerful CSP for preparative chiral separations", Lecture presented at the 8th International Symposium on Chirality ISCD 7, Edinburgh, UK, July 1996.
65. Okamoto, Y., Kawashima, M., Yamamoto, K. and Hatada, K., "Chromatographic resolution, 6: Useful chiral packing materials for high-performance liquid chromatographic resolution. Cellulose triacetate and tribenzoate coated on macroporous silica gel", Chem. Lett., 1984, 739-742.
66. Okamoto, Y. and Kaida, Y., "Resolution by high-performance liquid chromatography using polysaccharide carbamates and benzoates as chiral stationary phases", J. Chromatogr. A, 1994, 666, 403-419.
67. Francotte, E., "Enantioselective liquid chromatography: a mature separation technology?" Lecture presented at the 14th International Symposium on Chirality ISCD 14, Hamburg, Germany, Sept. 2003.
68. Terfloth, G., "Enantioseparations in super- and subcritical fluid chromatography", J. Chromatogr. A, 2001, 906, 301-307.
69. Tachibana, K. and Ohnishi, A., "Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases", J. Chromatogr. A, 2001, 906, 127-154.
70. Hamende, M. and Cavoy, E., "Chiral chromatography: from analytical to production scale", Chim. Nouv., 2000, 18, 3124-3126.
71. Nicoud, R.M., "The separation of optical isomers by simulated moving bed chromatography (Part II)", Pharm. Technol. Eur., 1999, 11, 28-41.
72. Schwanghart, A.-D., Backmann, W. and Blaschke, G., "Untersuchung chromatographischer Racemattrennungen, VII. Pr̈aparative Trennversuche an optisch aktiven Polyamiden", Chem. Ber., 1977, 110, 778- 787.
73. Blaschke, G., Br̈oker,W. and Fraenkel,W., "Enantiomerentrennung durch HPLC an Silicagel-gebundenen optisch aktiven Polyamiden", Angew. Chem., 1986, 98, 808-810.
74. Kinkel, J.N., Fraenkel,W. and Blaschke, G., "Enantiomerentrennung an polymer belegten chiralen Kieselgelen", Kontakte (Darmstadt), 1987, 3-14.
75. Arlt, D., B̈omer, B., Grosser, R. and Lange, W., "Neue chirale station̈are Polyamid-Phasen f̈ur die chromatographische Enantiomerentrennung", Angew. Chem., 1991, 103, 1685-1687.
76. Kinkel J.N., Reichert, K. and Kn̈oll, P., "Pr̈aparative chromatographische Enantiomerentrennung", GIT Fachz. Lab. Supplement 3/89 Chromatographie, 1989, 104-112.
77. Seebach, D., M̈uller, S.G., Gysel, U. and Zimmermann, J., "Pr̈aparative chromatographische Enantiomerentrennung von synthetisch n̈utzlichen cyclischen Acetalen", Helv. Chim. Acta, 1988, 71, 1303-1317.
78. Allenmark, S.G., Andersson, S., M̈oller, P. and Sanchez, D., "A new class of network-polymeric chiral stationary phases", Chirality, 1995, 7, 248-256.
79. M̈oller, P., Sanchez, D., Persson, B., Andersson, S. and Allenmark, S., "The use of network-polymeric chiral stationary phases for preparative chromatographic separation", Reprint from Poster presented at 11th International Symposium on Preparative and Industrial Chromatography, Baden-Baden, Oct. 1994; Akzo Nobel (ed.), Bohus, Sweden.
80. Andersson, S.,M̈oller, P., Persson, B., Sanchez, D. and Allenmark, S., "Analytical and preparative scale chromatographic separation of chiral compounds using immobilised acetylated diallyl tartardiamide network polymers". Reprint from Poster presented at the Euchem-Conference on Mechanisms of Chiral Recognition and the Design of Chiral Phase Systems, G̈oteborg, Sweden, Aug. 1995; Akzo Nobel (ed.), Bohus, Sweden.
81. M̈oller, P., "High performance silica for preparative chromatography: important characteristics and some new applications". In Subramanian, G. (ed.), Proceedings of EuroTech '98, Preparative & Process Scale Separations, Cambridge, Apr. 1998.
82. Pirkle,W.H. and Sikkenga, D.L., "Resolution of optical isomers by liquid chromatography", J. Chromatogr., 1976, 123, 400-404.
83. Pirkle,W.H., Finn, J.M., Hamper, B.C. Schreiner, J. and Pribish, J.A., "A useful and conveniently accessible chiral stationary phase for the liquid chromatographic separation of enantiomers". In Eliel, E.L. and Otsuka, S. (eds), Asymmetric Reactions and Processes in Chemistry, ACS Symposium Series No. 185,Washington, DC, 1982, pp. 245-260.
84. Pirkle, W.H. and Pochapsky, T.C., "Chiral stationary phases for the direct LC separation of enantiomers", Adv. Chromatogr., 1987, 27, 73-127.
85. Caude, M., Tambut́e, A. and Siret, L., "Chiral stationary phases derived from tyrosine", J. Chromatogr., 1991, 550, 357-382.
86. Gasparrini, F., Misiti, D. and Villani, C., "Chromatographic optical resolution on trans-1, 2-diaminocyclohexane derivatives: theory and applications", Chirality, 1992, 4, 447-458.
87. Uray, G., Maier, N.M. and Lindner, W., "Diphenylethanediamine derivatives as chiral selectors, III: Comparison of four new diastereomeric chiral stationary phases prepared by addition of mono-3,5-dinitrobenzoyldiphenylenediamine derivatives to optically pure epoxy silica", J. Chromatogr. A, 1994, 666, 41-53.
88. Pirkle, W.H., Ho Hyun, M. and Bank, B., "A rational approach to the design of highly-effective chiral stationary phases", J. Chromatogr., 1984, 316, 585-604.
89. Pirkle, W.H. and Ho Hyun, M., "A chiral stationary phase for the facile resolution of amino acids, amino alcohols, and amines as the 3,5-dinitrobenzoyl derivatives", J. Org. Chem., 1984, 49, 3043-3050.
90. Pirkle, W.H. and Welch, C.J., "An improved chiral stationary phase for the chromatographic separation of underivatized naproxen enantiomers", J. Liquid. Chromatogr., 1992, 15, 1947-1955.
91. Welch, C.J., "Analytical and semi-preparative separation of enantiomers using the Whelk-O 1 chiral stationary phase: naproxen and abscisic acid as case studies"; Chem. N.Z., 1993, 57, 9-10.
92. Pirkle, W.H. and Welch, C.J., "An investigation into the role of solvation in a well characterised chiral recognition system", J. Liq. Chromatogr., 1991, 14, 2027-2042.
93. Welch, C.J., "Evolution of chiral stationary phase design in the Pirkle laboratories", J. Chromatogr., 1994, 666, 3-26.
94. Pirkle,W.H. and Ho Hyun, M., "Reversed-phase chromatographic resolution of N-(3,5-dinitrobenzoyl)-_-amino acids on chiral stationary phases", J. Chromatogr., 1985, 322, 287-293.
95. Pirkle, W.H. and Murray, P.G., "The separation of the enantiomers of a variety of non-steroidal antiinflammatory drugs (NSAIDS) as their anilide derivatives using a chiral stationary phase", J. Liq. Chromatogr., 1990, 13, 2123-2134.
96. Harada, A., Furue, M. and Nozakura, S.-I., "Optical resolution of mandelic acid derivatives by column chromatography on crosslinked cyclodextrin gels", J. Polym. Sci., 1978, 16, 189-196.
97. Zsadon, B., D́ecsei, L., Szilasi, M. and T̈udos, F., "Inclusion chromatography of enantiomers of indole alkaloids on a cyclodextrin polymer stationary phase", J. Chromatogr., 1983, 270, 127-134.
98. Haan, S.M. and Armstrong, D.W., "HPLC separation of enantiomers and other isomers with cyclodextrinbonded phases: rules for chiral recognition". In Krstulovic A.M. (ed.), Chiral Separations by HPLC, Ellis Horwood Ltd., Chichester, UK, 1989, pp. 208-284.
99. Cabrera, K. and Lubda, D., "Chemically-bonded _-cyclodextrin as chiral stationary phase for the separation of enantiomers of pharmaceutical drugs", Chromatographie, 1992, 2 (GIT Spezial), 77-79.
100. Shaw, C.J., Sanfilippo, P.J., McNally, J.J., Ae Park S. and Press, J.B., "Analytical and preparative highperformance liquid chromatographic separation of thienopyran enantiomers", J. Chromatogr., 1993, 631, 173-175.
101. Kinkel, J.N. and Dingenen, J., "Preparative chromatographic enantiomer separations: possibilities and limitations". Lecture presented at the 3rd International Symposium on Chiral Discrimination, T̈ubingen, Germany, Oct. 1992.
102. Armstrong, D.W., Hilton, M. and Coffin, L., "Multimodal chiral stationary phases for liquid chromatography: (R)- and (S)-naphthylethyl-carbamate-derivatized _-cyclodextrin", LC-GC Int., 1992, 5, 28-36.
103. Chang, S.C., Reid, G.L., Cheng, S., Chang, C.D. and Armstrong, D.W., "Evaluation of a new polar-organic high-performance liquid chromatographic mobile phase for cyclodextrin-bonded chiral stationary phases", Trends Anal. Chem., 1993, 12, 144-153.
104. Armstrong, D.W., Tang, Y., Chen, S., Zhou, Y., Bagwill, C. and Chen, J.R., "Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography"; Anal. Chem., 1994, 66, 1473-1484
105. Armstrong, D.W., Liu, Y. and Ekborg-Ott, K.H., "A covalently bonded teicoplanin chiral stationary phase for HPLC enantioseparations", Chirality, 1995, 7, 474-497.
106. Liu, Y., Berthod, A., Mitchell, C.R., Xiao, T.L., Zhang, V. and Armstrong, D.W., "Super /subcritical fluid chromatography chiral separations with macrocyclic glycopeptide stationary phases", J. Chromatogr. A, 2002, 978, 185-204.
107. D'Acquarica, I., Gasparrini, F., Misiti, D., Zappia, G., Cimarelli, C., Palmieri, G., Carotti, A., Cellamare, S. and Villani, C., "Application of a new chiral stationary phase containing the glycopeptide antibiotic A-40,926 in the direct chromatographic resolution of _-amino acids", Tetrahedron Asymm., 2000, 11, 2375-2385.
108. Lee, T.J. and Beesley, T.E., "Multi-modal, preparative chiral purifications using macrocyclic glycopeptide phases", EAS 2000; Atlantic City, NJ. Available at: http://www.astecusa.com/publications/presentations/presentations.htm.
109. Davankov, V.A., Navratil, J.D. and Walton, H.F., Ligand Exchange Chromatography; CRC Press, Boca Raton, FL,1988.
110. Davankov, V.A., Bochkov, A.S., Kurganov, A.A., Roumeliotis, P. and Unger, K.K., "Ligand-exchange chromatography, 13: Separation of unmodified _-amino acid enantiomers by reverse phase HPLC", Chromatographia, 1980, 13, 677-685.
111. Jeanneret-Gris, G., Soerensen, C., Su, H. and Porret, J., "Direct preparative resolution of racemic aminoacids using ligand exchange chromatography (Chirallec)", Chromatographia, 1989, 28, 337-340.
112. Wulff, G., Sarhan, A. and Zabrocki, K., "Enzyme-analogue built polymers and their use for the resolution of racemates" Tetrahedron Lett., 1973, 44, 4329-4332.
113. Mosbach, K., "Molecular imprinting", Trends Biochem. Sci., 1994, 19, 9-14.
114. Sellergen, B., "Imprinted chiral stationary phases in high-performance liquid chromatography", J. Chromatogr. A, 2001, 906, 227-252.
115. Haginaka, J., Takehira, H., Hosoya, K. and Tanaka, N., "Uniform-sized molecularly imprinted polymer for (S)-naproxen selectively modified with hydrophilic external layer", J. Chromatogr., 1999, 849, 331-339.
116. Sellergen, B., Lepisto, M. and Mosbach, K., "Highly enantioselective and substrate-selective polymers obtained by molecular imprinting utilizing noncovalent interactions. NMR and chromatographic studies on the nature of recognition", J. Am. Chem. Soc., 1988, 110, 5853-5860.
117. Fischer, L., M̈uller, R., Ekkberg, B. and Mosbach, K., "Direct enantioseparation of _-adrenergic blockers using a chiral stationary phase prepared by molecular imprinting", J. Am. Chem. Soc., 1991, 113, 9358- 9360.
118. Schulte, M., Ditz, R., Devant, R.M., Kinkel, J.N. and Charton, F., "Comparison of the specific productivity of different chiral stationary phases used for simulated moving-bed chromatography", J. Chromatogr. A, 1997, 769, 93-100.
119. Cox, G.B., "Packing materials for enantioselective preparative chromatography", Anal. Mag., 1998, 26, M71-M76.
120. Wallworth, D., "Polar mobile phase design and bonding chemistries for the efficient analytical or preparative separation of drug enantiomers". Lecture presented at Separation, Purification and Analysis in Drug Discovery, L̈okeberg, Sweden, June 20-23, 2004.
121. Wu, D.-R., Lohse, K. and Lin, L., "Preparative chiral purification of enantiomers using covalently-bonded chiral stationary phases". In Book of Abstracts of the 23rd International Symposium on HPLC (HPLC '99), Granada, May 30-June 4, 1999.
122. Kinkel, J.N., "Optically active polyacrylamide/silica composites and related packings and their application in chiral separations". In Subramanian, G. (ed.), A Practical Approach to Chiral Separations by Liquid Chromatography; VCH Publishers, Weinheim, 1994, pp. 217-277.
123. Yashima, E. and Okamoto,Y., "Chiral discrimination on polysaccharide derivatives", Bull. Chem. Soc. Jpn., 1995, 68, 3289-3307.
124. Blaschke, G., "Chromatographic resolution of chiral drugs on polyamides and cellulose triacetate", J. Liq. Chromatogr., 1986, 9, 341-368.
125. Blaschke, G. and Markgraf, H., "Trennung chiraler N-Methylbarbiturate und Phenylcyanessigester an Cellulosetriaceate", Arch. Pharm., 1984, 317, 465-471.
126. Schl̈ogl, K. and Widhalm, M., "Preparative enantiomeric resolution of axial- and planar-chiral benzene derivatives, metallocenes, and ethanoaza[10]annulenes by medium-pressure chromatography on triacetylcellulose", Chem. Ber., 1982, 115, 3042-3048.
127. Isaksson, R. and Rochester, J., "Preparative and analytical enantiomer separation of some_4-1,3-thiazoline-2-thiones on swollen microcrystalline triacetylcellulose", J. Org. Chem., 1985, 50, 2519-2521.
128. Blaschke, G. and Donow, F., "Chromatographic resolutions of racemates, IV: Separation efficiency of optically active poly[N-((S)-1-phenylethyl)acrylamide] depending on the polymerisation procedure", Chem. Ber., 1975, 108, 1188-1197.
129. Davankov, V.A., "Chiral selectors with chelating properties in liquid chromatography: fundamental reflections and selective review of recent developments", J. Chromatogr. A, 1994, 666, 55-76.
130. Lipkowitz, B.K., "Atomistic modeling of enantioselection in chromatography", J. Chromatogr. A, 2001, 906, 417-442.
131. Francotte, E., "Chiral chromatography: an essential and versatile tool in the research and in the development of bioactive compounds", Chim. Nouv., 1996, 14, 1541-1552.
132. Tachibana, K., "Enhancing the separation of polysaccharide based chiral stationary phases". Lecture presented at the International Symposium on Chirality ISCD 15, Shizuoka, Japan, Oct. 2003.
133. Franco, P., "Separation of enantiomers by chromatography: a strategic methodology in drug and fine chemical development". Lecture presented at Chirasource 2003, Barcelona, Spain, Dec. 2003.
134. L̈ammerhofer, M. and Lindner, W., "Quinine and quinidine derivatives as chiral selectors I. Brush type chiral stationary phases for high-performance liquid chromatography based on cinchonan carbamates and their application as chiral anion exchangers", J. Chromatogr. A, 1996, 741, 33-48.
135. Piette, V., L̈ammerhofer, M., Bischoff, K. and Lindner, W., "High-performance liquid chromatographic enantioseparation of N-protected _-amino acids using nonporous silica modified by a quinine carbamate as chiral stationary phase", Chirality, 1997, 9, 157-161.
136. Mandl, A., Nicoletti, L., L̈ammerhofer,M. and Lindner,W., "Quinine versus carbamoylated quinine-based chiral anion exchangers. A comparison regarding enantioselectivity for N-protected amino acids and other chiral acids", J. Chromatogr. A, 1999, 858, 1-11.
137. Pirkle, W.H. and Welch, C.J., "An improved chiral stationary phase for the chromatographic separation of underivatized naproxen enantiomers", J. Liq. Chromatogr., 1992, 15, 1947-1955.
138. Pirkle, W.H. and Koscho, M.E., "Structural optimisation of a chiral selector for use in preparative enantioselective chromatography", J. Chromatogr. A, 1999, 840, 151-158.
139. Murer, P., Lewandowski, K., Svec, F. and Frechet, J.M., "On-bead combinatorial approach to the design of chiral stationary phases for HPLC", Anal. Chem., 1999, 71, 1278-1284.
140. Murer, P., Lewandowski, K., Svec, F. and Frechet, J.M., "Combinatorial 'library on bead' approach to polymeric materials with vastly enhanced chiral recognition", Chem. Commun., 1998, 2559-2560.
141. Welch, C.J., Bhat, G. and Protopopova, M.N., "Selection of an optimized adsorbent for preparative chromatographic enantioseparation by microscale screening of a second-generation chiral stationary phase library" J. Comb. Chem., 1999, 1, 364-367.
142. Welch, C.J., Protopopova, M.N. and Bhat, G., "Microscale synthesis and screening of chiral stationary phases", Enantiomer, 1998, 3, 471-476.
143. Wu, Y., Wan, Y., Yang, A. and Li, T., "Screening of mixture combinatorial libraries for chiral selectors: a reciprocal chromatographic approach using enantiomeric libraries", Anal. Chem., 1999, 71, 1688-1691.
144. Lewandowski, K., Murer, P., Svec, F. and Frechet, J.M., "A combinatorial approach to recognition of chirality: preparation of highly enantioselective aryl-dihydropyrimidine selectors for chiral HPLC", J. Comb. Chem., 1999, 1, 105-112.
145. Okamoto, Y., Aburatani, R., Miura, S.-I. and Hatada, K., "Chiral stationary phases for HPLC: cellulose tris(3,5-dimethylphenylcarbamate) and tris(3,5-dichlorophenylcarbamate) chemically bonded to silica gel", J. Liq. Chromatogr., 1987, 10, 1613-1628.
146. Yashima, E., Fukaya, H. and Okamoto, Y., "3,5-Dimethylphenylcarbamates of cellulose and amylose regioselectively bonded to silica gel as chiral stationary phases for high-performance liquid chromatography", J. Chromatogr. A, 1994, 677, 11-19.
147. Franco, P., Lopez, P., Minguillon, C. and Oliveros, L., "Chiral chromatographic discrimination ability of a cellulose 3,5-dimethylphenylcarbamate/10-undecenoate mixed derivative fixed on several chromatographic matrixes", J. Liq. Chromatogr., 1995, 18, 1521-1532.
148. Franco, P., Oliveros, L. and Minguillon, C., "Solvent versatility of bonded cellulose-derived chiral stationary phases for high-performance liquid chromatography and its consequences in column loadability", J. Chromatogr. A, 1998, 793, 239-247.
149. Franco, P., Senso, A., Oliveros, L. and Minguillon, C., "Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography", J. Chromatogr. A, 2001, 906, 155-170.
150. Oliveros, L., Minguillon, C., Serkiz, B., Meunier, F., Volland, J.-P. and Cordi, A.A., "Preparative isolation of the eutomer of cyclothiazide by high-performance liquid chromatography on a cellulose-derived chiral stationary phase with toluene-acetone as the mobile phase", J. Chromatogr. A, 1996, 729, 29-32.
151. Royo, S., Ĺopez, P., Jiḿenez, A.I., Oliveros, L. and Cativiela, C., "First synthesis of the two enantiomers of _-methyldiphenylalanine [(_Me)Dip] by HPLC resolution", Chirality, 2002, 14, 39-46.
152. Francotte, E. and Zhang, T., "Photochemically crosslinked polysaccharide derivatives having no photopolymerizable functional groups", European Patent WO 97/04011 (Priority July 21, 1995), 1997.
153. Francotte, E., "Thermally immobilised polysaccharide derivatives", European Patent WO 97/49733 (Priority June 27, 1996), 1997.
154. Francotte, E.R., "Enantioselective chromatography. An essential and versatile tool for the analytical and preparative separation of enantiomers", Chimia, 1997, 51, 717-725.
155. Mayer, S., Briand, X. and Francotte, E., "Separation of enantiomers by packed capillary electrochromatography on a cellulose-based stationary phase", J. Chromatogr. A, 2000, 875, 331-339.
156. Francotte, E. and Huynh, D., "Immobilised halogenophenylcarbamate derivatives of cellulose as novel stationary phases for enantioselective drug analysis", J. Pharm. Biomed. Anal., 2002, 27, 421-429.
157. Francotte, E., "History and future of preparative enantioselective HPLC". Lecture presented at the 15th International Symposium on Chirality ISCD 15, Shizuoka, Japan, Oct. 2003.