Monoliths with chiral surface functionalization for enantioselective capillary electrochromatography

Journal of Pharmaceutical and Biomedical Analysis

Volumn 53, Issue 5, 2010, Pages 1091-1123

  Lämmerhofer, Michael ^a   Gargano, Andrea ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

Capillary electrochromatography; Chiral stationary phase; Enantiomer separation; Molecularly imprinted polymer; Organic polymer and silica monolith

Indexed keywords

ALPRENOLOL; ATENOLOL; BACLOFEN; BUPIVACAINE; CARPROFEN; FELODIPINE; IBUPROFEN; INDAPAMIDE; KETOPROFEN; MEBEVERINE; MEFLOQUINE; MEPIVACAINE; METOPROLOL; MEXILETINE; NAPROXEN; NORMESUXIMIDE; OXAZEPAM; OXYBUTYNIN; PINDOLOL; POLYACRYLAMIDE; POLYMER; PRAZIQUANTEL; PRENALTEROL; PROPRANOLOL; ROPIVACAINE; SILICON DIOXIDE; TETRAHYDROPALMATINE; THALIDOMIDE; UNINDEXED DRUG; WARFARIN;

CAPILLARY ELECTROCHROMATOGRAPHY; CHEMISTRY; CHIRALITY; ENANTIOMER; ION EXCHANGE; PRIORITY JOURNAL; REVIEW; SYNTHESIS;

ANIMALS; CAPILLARY ELECTROCHROMATOGRAPHY; HUMANS; PHARMACEUTICAL PREPARATIONS; STEREOISOMERISM; SURFACE PROPERTIES;

EID: 77955925679     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2010.05.026     Document Type: Review

References (144)

1. F. Svec, T.B. Tennikova, Z. Deyl (Eds.), Monolithic materials: preparation, properties and applications, J. Chromatogr. Libr. 67, Elsevier, Amsterdam, 2003.
2. Urban J., Jandera P. Polymethacrylate monolithic columns for capillary liquid chromatography. J. Sep. Sci. 2008, 31:2521-2540.
3. Hilder E.F., Svec F., Frechet J.M.J. Development and application of polymeric monolithic stationary phases for capillary electrochromatography. J. Chromatogr. A 2004, 1044:3-22.
4. Bedair M., El Rassi Z. Recent advances in polymeric monolithic stationary phases for electrochromatography in capillaries and chips. Electrophoresis 2004, 25:4110-4119.
5. Klodzinska E., Moravcova D., Jandera P., Buszewski B. Monolithic continuous beds as a new generation of stationary phase for chromatographic and electro-driven separations. J. Chromatogr. A 2006, 1109:51-59.
6. Z. Deyl, F. Svec (Eds.), Capillary electrochromatography, J. Chromatogr. Libr 62, Elsevier, Amsterdam, 2001.
7. Svec F. Porous polymer monoliths: amazingly wide variety of techniques enabling their preparation. J. Chromatogr. A 2010, 1217:902-924.
8. Hjertén S., Liao J.-L., Zhang R. High-performance liquid chromatography on continuous polymer beds. J. Chromatogr. 1989, 473:273-275.
9. Tennikova T.B., Belenkii B.G., Svec F. High-performance membrane chromatography. A novel method of protein separation. J. Liq. Chromatogr. 1990, 13:63-70.
10. Hjerten S., Vegvari A., Srichaiyo T., Zhang H.-X., Ericson C., Eaker D. An approach to ideal separation media for (electro)chromatography. J. Capill. Electrophor. 1998, 5:13-26.
11. Schmid M.G., Grobuschek N., Tuscher C., Gubitz G., Vegvari A., Machtejevas E., Maruska A., Hjerten S. Chiral separation of amino acids by ligand-exchange capillary electrochromatography using continuous beds. Electrophoresis 2000, 21:3141-3144.
12. Vegvari A., Foldesi A., Hetenyi C., Kocnegarova O., Schmid M.G., Kudirkaite V., Hjerten S. A new easy-to-prepare homogeneous continuous electrochromatographic bed for enantiomer recognition. Electrophoresis 2000, 21:3116-3125.
13. Kornysova O., Owens P.K., Maruska A. Continuous beds with vancomycin as chiral stationary phase for capillary electrochromatography. Electrophoresis 2001, 22:3335-3338.
14. Minakuchi H., Nakanishi K., Soga N., Ishizuka N., Tanaka N. Octadecylsilylated porous silica rods as separation media for reversed-phase liquid chromatography. Anal. Chem. 1996, 68:3498-3501.
15. Q. Tang, M.L. Lee, Monolithic columns prepared from particles, in: F. Svec, T.B. Tennikova, Z. Deyl (Eds.), Monolithic Materials: Preparation, Properties and Applications, J. Chromatogr. Libr. 62, Elsevier, Amsterdam, 2003, pp. 197-211.
16. Lammerhofer M., Svec F., Frechet J.M.J., Lindner W. Separation of enantiomers by capillary electrochromatography. Trends Anal. Chem. 2000, 19:676-698.
17. Fanali S., Catarcini P., Blaschke G., Chankvetadze B. Enantioseparations by capillary electrochromatography. Electrophoresis 2001, 22:3131-3151.
18. Lämmerhofer M., Lindner W. Capillary electrochromatography. Monolithic Materials: Preparation, Properties and Applications 2003, 489-559. Elsevier, Amsterdam. F. Svec, T.B. Tennikova, Z. Deyl (Eds.).
19. Fujimoto C. Enantiomer separation by capillary electrochromatography using fritless packed columns. Anal. Sci. 2002, 18:19-25.
20. Qin F., Xie C., Yu Z., Kong L., Ye M., Zou H. Monolithic enantiomer-selective stationary phases for capillary electrochromatography. J. Sep. Sci. 2006, 29:1332-1343.
21. Wistuba D., Schurig V. Comparison of monolithic approaches for enantioselective capillary electrochromatography involving cyclodextrins. J. Sep. Sci. 2006, 29:1344-1352.
22. Preinerstorfer B., Laemmerhofer M. Recent accomplishments in the field of enantiomer separation by CEC. Electrophoresis 2007, 28:2527-2565.
23. Tanret I., Mangelings D., Vander Heyden Y. Monolithic stationary phases in classic and chiral pharmaceutical analysis with CEC and pCEC. J. Chromatogr. Sci. 2009, 47:407-417.
24. Guttman A., Paulus A., Cohen S., Grinberg N., Karger B.L. Use of complexing agents for selective separation in high-performance capillary electrophoresis. Chiral resolution via cyclodextrins incorporated within polyacrylamide gel columns. J. Chromatogr. 1988, 448:41-53.
25. Cruzado I.D., Vigh G. Chiral separations by capillary electrophoresis using cyclodextrin-containing gels. J. Chromatogr. 1992, 608:421-425.
26. Birnbaum S., Nilsson S. Protein-based capillary affinity gel electrophoresis for the separation of optical isomers. Anal. Chem. 1992, 64:2872-2874.
27. Teraguchi M., Ohtake M., Inoue H., Yoshida A., Aoki T., Kaneko T., Yamanaka K. Preparation of chiral polystyrene monoliths by utilizing W/O emulsion polymerization and their optical resolution ability. J. Polym. Sci. Part A: Polym. Chem. 2005, 43:2348-2357.
28. Götmar G., Fornstedt T., Guiochon G. Apparent and true enantioselectivity in enantioseparations. Chirality 2000, 12:558-564.
29. Lämmerhofer M. Chiral recognition by enantioselective liquid chromatography: mechanisms and modern chiral stationary phases. J. Chromatogr. A 2010, 1217:814-856.
30. Sinner F.M., Buchmeiser M.R. Ring opening metathesis polymerization: access to a new class of functionalized, monolithic stationary phases for liquid chromatography. Angew. Chem. Int. Ed. 2000, 39:1433-1436.
31. Sinner F., Buchmeiser M.R. A new class of continuous polymer supports prepared by ring-opening metathesis polymerization: a straightforward route to functionalized monoliths. Macromolecules 2000, 33:5777-5786.
32. Mayr B., Sinner F., Buchmeiser M.R. Chiral beta-cyclodextrin-based polymer supports prepared via ring-opening metathesis graft-polymerization. J. Chromatogr. A 2001, 907:47-56.
33. Zeng H.-L., Li H.-F., Lin J.-M. Chiral separation of dansyl amino acids by PDMS microchip gel monolithic column electrochromatography with γ-cyclodextrin bonded in polyacrylamide. Anal. Chim. Acta 2005, 551:1-8.
34. Zeng H.-L., Li H., Xu W., Lin J.-M. Chiral separation of FITC-labeled amino acids with gel electrochromatography using a polydimethylsiloxane microfluidic device. J. Capill. Electrophor. Microchip Technol. 2007, 10:19-24.
35. Schmid M.G., Grobuschek N., Lecnik O., Gubitz G., Vegvari A., Hjerten S. Enantioseparation of hydroxy acids on easy-to-prepare continuous beds for capillary electrochromatography. Electrophoresis 2001, 22:2616-2619.
36. Laemmerhofer M., Peters E.C., Yu C., Svec F., Frechet J.M.J., Lindner W. Chiral monolithic columns for enantioselective capillary electrochromatography prepared by copolymerization of a monomer with quinidine functionality. 1. Optimization of polymerization conditions, porous properties, and chemistry of the stationary phase. Anal. Chem. 2000, 72:4614-4622.
37. Laemmerhofer M., Svec F., Frechet J.M.J., Lindner W. Chiral monolithic columns for enantioselective capillary electrochromatography prepared by copolymerization of a monomer with quinidine functionality. 2. Effect of chromatographic conditions on the chiral separations. Anal. Chem. 2000, 72:4623-4628.
38. Laemmerhofer M., Tobler E., Zarbl E., Lindner W., Svec F., Frechet J.M.J. Macroporous monolithic chiral stationary phases for capillary electrochromatography: new chiral monomer derived from cinchona alkaloid with enhanced enantioselectivity. Electrophoresis 2003, 24:2986-2999.
39. Lammerhofer M., Svec F., Frechet J.M.J., Lindner W. Monolithic stationary phases for enantioselective capillary electrochromatography. J. Microcol. Sep. 2000, 12:597-602.
40. Svec F., Frechet J.M.J. Molded rigid monolithic porous polymers: an inexpensive, efficient, and versatile alternative to beads for the design of materials for numerous applications. Ind. Eng. Chem. Res. 1999, 38:34-48.
41. Peters E.C., Petro M., Svec F., Frechet J.M.J. Molded rigid polymer monoliths as separation media for capillary electrochromatography. 1. Fine control of porous properties and surface chemistry. Anal. Chem. 1998, 70:2288-2295.
42. Fujimoto C. Charged polyacrylamide gels for capillary electrochromatographic separations of uncharged, low molecular weight compounds. Anal. Chem. 1995, 67:2050-2053.
43. Zhang M., El Rassi Z. Capillary electrochromatography with polyacrylamide monolithic stationary phases having bonded dodecyl ligands and sulfonic acid groups: evaluation of column performance with alkyl phenyl ketones and neutral moderately polar pesticides. Electrophoresis 2001, 22:2593-2599.
44. Yu C., Svec F., Frechet J.M.J. Towards stationary phases for chromatography on a microchip: molded porous polymer monoliths prepared in capillaries by photoinitiated in situ polymerization as separation media for electrochromatography. Electrophoresis 2000, 120-127.
45. Svec F., Peters E.C., Sykora D., Frechet J.M.J. Design of the monolithic polymers used in capillary electrochromatography columns. J. Chromatogr. A 2000, 887:3-29.
46. Peters E.C., Lewandowski K., Petro M., Svec F., Frechet J.M.J. Chiral electrochromatography with a 'molded' rigid monolithic capillary column. Anal. Commun. 1998, 35:83-86.
47. Koide T., Ueno K. Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with charged polyacrylamide gels incorporating chiral selectors. Anal. Sci. 1998, 14:1021-1023.
48. Koide T., Ueno K. Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with beta-cyclodextrin-bonded charged polyacrylamide gels. Anal. Sci. 1999, 15:791-794.
49. Lin J.-M., Nakagama T., Uchiyama K., Hobo T. Capillary electrochromatographic separation of amino acid enantiomers using on-column prepared molecularly imprinted polymer. J. Pharmaceut. Biomed. Anal. 1997, 15:1351-1358.
50. Schweitz L., Andersson L.I., Nilsson S. Capillary electrochromatography with molecular imprint-based selectivity for enantiomer separation of local anesthetics. J. Chromatogr. A 1997, 792:401-409.
51. Schweitz L., Andersson L.I., Nilsson S. Capillary electrochromatography with predetermined selectivity obtained through molecular imprinting. Anal. Chem. 1997, 69:1179-1183.
52. Laemmerhofer M. Chirally-functionalized monolithic materials for stereoselective capillary electrochromatography. Anal. Bioanal. Chem. 2005, 382:873-877.
53. Koide T., Ueno K. Enantiomeric separations by capillary electrochromatography with charged polyacrylamide gels incorporating chiral selectors. Anal. Sci. 2000, 16:1065-1070.
54. Koide T., Ueno K. Enantiomeric separations of cationic and neutral compounds by capillary electrochromatography with monolithic chiral stationary phases of beta-cyclodextrin-bonded negatively charged polyacrylamide gels. J. Chromatogr. A 2000, 893:177-187.
55. Koide T., Ueno K. Enantiomeric separations of acidic and neutral compounds by capillary electrochromatography with beta-cyclodextrin-bonded positively charged polyacrylamide gels. J. High Resolut. Chromatogr. 2000, 23:59-66.
56. Kornysova O., Machtejevas E., Kudirkaite V., Pyell U., Maruska A. Synthesis and characterization of polyrotaxane-based polymeric continuous beds for capillary electrochromatography. J. Biochem. Biophys. Methods 2002, 50:217-232.
57. Kornysova O., Surna R., Snitka V., Pyell U., Maruska A. Polyrotaxane approach for synthesis of continuous beds for capillary electrochromatography. J. Chromatogr. A 2002, 971:225-235.
58. Koide T., Ueno K. Enantiomeric separations of primary amino compounds by capillary electrochromatography with monolithic chiral stationary phases of chiral crown ether-bonded negatively charged polyacrylamide gels. J. Chromatogr. A 2001, 909:305-315.
59. Lecnik O., Guebitz G., Schmid M.G. Role of the charge in continuous beds in the chiral separation of hydroxy acids by ligand-exchange capillary electrochromatography. Electrophoresis 2003, 24:2983-2985.
60. Machtejevas E., Maruska A. A new approach to human serum albumin chiral stationary phase synthesis and its use in capillary liquid chromatography and capillary electrochromatography. J. Sep. Sci. 2002, 25:1303-1309.
61. A. Maruska, Capillary electrochromatography, in: F. Svec, T.B. Tennikova, Z. Deyl (Eds.), Monolithic Materials: Preparation, Properties and Applications, J. Chromatogr. Libr. 67, Elsevier, Amsterdam, 2003, pp. 143-172.
62. Schweitz L., Andersson L.I., Nilsson S. Molecular imprint-based stationary phases for capillary electrochromatography. J. Chromatogr. A 1998, 817:5-13.
63. P. Spegel, J. Nilsson, S. Nilsson, Chiral separations by capillary electrochromatography using molecularly imprinted polymers, in: G. Gübitz, M.G. Schmid (Eds.), Chiral Separations, Series: Methods in Molecular Biology, Vol. 243, Humana Press, Totowa, NJ, United States, 2004, pp. 411-424.
64. Schweitz L., Spegel P., Nilsson S. Molecularly imprinted microparticles for capillary electrochromatographic enantiomer separation of propranolol. Analyst 2000, 125:1899-1901.
65. Lin J.M., Nakagama T., Wu X.Z., Uchiyama K., Hobo T. Capillary electrochromatographic separation of amino acid enantiomers with molecularly imprinted polymers as chiral recognition agents. Fresenius' J. Anal. Chem. 1997, 357:130-132.
66. Lin J.-M., Nakagama T., Uchiyama K., Hobo T. Capillary electrochromatographic separation of amino acid enantiomers using on-column prepared molecularly imprinted polymer. J. Pharm. Biomed. Anal. 1997, 15:1351-1358.
67. Liu Z.-S., Xu Y.-L., Wang H., Yan C., Gao R.-Y. Chiral separation of binaphthol enantiomers on molecularly imprinted polymer monolith by capillary electrochromatography. Anal. Sci. 2004, 20:673-678.
68. Xu Y.-L., Liu Z.-S., Wang H.-F., Yan C., Gao R.-Y. Chiral recognition ability of an (S)-naproxen-imprinted monolith by capillary electrochromatography. Electrophoresis 2005, 26:804-811.
69. Deng Q.-L., Lun Z.-H., Gao R.-Y., Zhang L.-H., Zhang W.-B., Zhang Y.-K. (S)-Ibuprofen-imprinted polymers incorporating gamma-methacryloxypropyl-trimethoxysilane for CEC separation of ibuprofen enantiomers. Electrophoresis 2006, 27:4351-4358.
70. Ou J., Li X., Feng S., Dong J., Dong X., Kong L., Ye M., Zou H. Preparation and evaluation of a molecularly imprinted polymer derivatized silica monolithic column for capillary electrochromatography and capillary liquid chromatography. Anal. Chem. 2007, 79:639-646.
71. Schweitz L., Andersson L.I., Nilsson S. Molecular imprinting for chiral separations and drug screening purposes using monolithic stationary phases in CEC. Chromatographia 1999, 49:S93-S94.
72. Schweitz L., Andersson L.I., Nilsson S. Rapid electrochromatographic enantiomer separations on short molecularly imprinted polymer monoliths. Anal. Chim. Acta 2001, 435:43-47.
73. Schweitz L., Andersson L.I., Nilsson S. Molecularly imprinted CEC sorbents: investigations into polymer preparation and electrolyte composition. Analyst 2002, 127:22-28.
74. Ou J., Dong J., Tian T., Hu J., Ye M., Zou H. Enantioseparation of tetrahydropalmatine and Troeger's base by molecularly imprinted monolith in capillary electrochromatography. J. Biochem. Biophys. Methods 2007, 70:71-76.
75. Spegel P., Schweitz L., Andersson L.I., Nilsson S. Novel vinylpyridine based cationic MIP monoliths for enantiomer separation in CEC. Chromatographia 2008, 69:277-285.
76. Li M., Lin X., Xie Z. Investigation of enantiomer recognition of molecularly imprinted polymeric monoliths in pressurized capillary electrochromatography screening the amino acids and their derivatives. J. Chromatogr. A 2009, 1216:5320-5326.
77. Rohr T., Hilder E.F., Donovan J.J., Svec F., Frechet J.M.J. Photografting and the control of surface chemistry in three-dimensional porous polymer monoliths. Macromolecules 2003, 36:1677-1684.
78. Eeltink S., Hilder E.F., Geiser L., Svec F., Frechet J.M.J., Rozing G.P., Schoenmakers P.J., Kok W.T. Controlling the surface chemistry and chromatographic properties of methacrylate-ester-based monolithic capillary columns via photografting. J. Sep. Sci. 2007, 30:407-413.
79. Sinner F.M., Buchmeiser M.R. Ring-opening metathesis polymerization: access to a new class of functionalized, monolithic stationary phases for liquid chromatography. Angew. Chem. Int. Ed. 2000, 39:1433-1436.
80. Mayr B.S., Buchmeiser M.R. Chiral beta-cyclodextrin-based polymer supports prepared via ring-opening metathesis graft-polymerization. J. Chromatogr. A 2001, 907:47-56.
81. Buchmeiser M.R. Stationary phases for chromatography prepared by ring opening metathesis polymerization. J. Sep. Sci. 2008, 31:1907-1922.
82. Dong X., Wu R.a., Dong J., Wu M., Zhu Y., Zou H. Polyacrylamide-based monolithic capillary column with coating of cellulose tris(3,5-dimethylphenyl-carbamate) for enantiomer separation in capillary electrochromatography. Electrophoresis 2008, 29:919-927.
83. Chankvetadze B. Monolithic chiral stationary phases for liquid-phase enantioseparation techniques. J. Sep. Sci. 2010, 33:305-314.
84. Kornysova O., Jarmalaviciene R., Maruska A. A simplified synthesis of polymeric nonparticulate stationary phases with macrocyclic antibiotic as chiral selector for capillary electrochromatography. Electrophoresis 2004, 25:2825-2829.
85. Preinerstorfer B., Bicker W., Lindner W., Lammerhofer M. Development of reactive thiol-modified monolithic capillaries and in-column surface functionalization by radical addition of a chromatographic ligand for capillary electrochromatography. J. Chromatogr. A 2004, 1044:187-199.
86. Preinerstorfer B., Lindner W., Laemmerhofer M. Polymethacrylate-type monoliths functionalized with chiral amino phosphonic acid-derived strong cation exchange moieties for enantioselective nonaqueous capillary electrochromatography and investigation of the chemical composition of the monolithic polymer. Electrophoresis 2005, 26:2005-2018.
87. Messina A., Flieger M., Bachechi F., Sinibaldi M. Enantioseparation of 2-aryloxypropionic acids on chiral porous monolithic columns by capillary electrochromatography,. J. Chromatogr. A 2006, 1120:69-74.
88. Messina A., Sinibaldi M. CEC enantioseparations on chiral monolithic columns: a study of the stereoselective degradation of (R/S)-dichlorprop [2-(2,4-dichlorophenoxy)propionic acid] in soil. Electrophoresis 2007, 28:2613-2618.
89. Tian Y., Zhong C., Fu E., Zeng Z. Novel beta-cyclodextrin derivative functionalized polymethacrylate-based monolithic columns for enantioselective separation of ibuprofen and naproxen enantiomers in capillary electrochromatography. J. Chromatogr. A 2009, 1216:1000-1007.
90. Li Y., Song C., Zhang L., Zhang W., Fu H. Fabrication and evaluation of chiral monolithic column modified by β-cyclodextrin derivatives. Talanta 2010, 80:1378-1384.
91. Guerrouache M., Millot M.-C., Carbonnier B. Functionalization of macroporous organic polymer monolith based on succinimide ester reactivity for chiral capillary chromatography: a cyclodextrin click approach. Macromol. Rapid Commun. 2009, 30:109-113.
92. Tian Y., Zhong C., Fu E., Zeng Z. Novel β-cyclodextrin derivative functionalized polymethacrylate-based monolithic columns for enantioselective separation of ibuprofen and naproxen enantiomers in capillary electrochromatography. J. Chromatogr. A 2009, 1216:1000-1007.
93. Ding G., Tang A. Preparation of norvancomycin-bonded chiral silica monolithic column for capillary electrochromatography and its applications. Sepu 2006, 24:402-406.
94. Siouffi A.M. Silica gel-based monoliths prepared by the sol-gel method: facts and figures. J. Chromatogr. A 2003, 1000:801-818.
95. Nakanishi K., Tanaka N. Sol-gel with phase separation. Hierarchically porous materials optimized for high-performance liquid chromatography separations. Acc. Chem. Res. 2007, 40:863-873.
96. Nakanishi K., Soga N. Phase separation in silica sol-gel system containing polyacrylic acid. I. Gel formation behavior and effect of solvent composition. J. Non-Cryst. Solids 1992, 139:1-13.
97. Núñez O., Nakanishi K., Tanaka N. Preparation of monolithic silica columns for high-performance liquid chromatography. J. Chromatogr. A 2008, 1191:231-252.
98. Ishizuka N., Kobayashi H., Minakuchi H., Nakanishi K., Hirao K., Hosoya K., Ikegami T., Tanaka N. Monolithic silica columns for high-efficiency separations by high-performance liquid chromatography. J. Chromatogr. A 2002, 960:85-96.
99. Dong X., Dong J., Ou J., Zhu Y., Zou H. Preparation and evaluation of a vancomycin-immobilized silica monolith as chiral stationary phase for CEC. Electrophoresis 2007, 28:2606-2612.
100. Dong X., Wu R.a., Dong J., Wu M., Zhu Y., Zou H. The covalently bonded cellulose tris(3,5-dimethylphenylcarbamate) on a silica monolithic capillary column for enantioseparation in capillary electrochromatography. J. Chromatogr. B 2008, 875:317-322.
101. Qin F., Xie C., Feng S., Ou J., Kong L., Ye M., Zou H. Monolithic silica capillary column with coated cellulose tris(3,5-dimethylphenylcarbamate) for capillary electrochromatographic separation of enantiomers. Electrophoresis 2006, 27:1050-1059.
102. Preinerstorfer B., Lubda D., Lindner W., Laemmerhofer M. Monolithic silica-based capillary column with strong chiral cation-exchange type surface modification for enantioselective non-aqueous capillary electrochromatography. J. Chromatogr. A 2006, 1106:94-105.
103. Chen Z., Hobo T. Chemically l-prolinamide-modified monolithic silica column for enantiomeric separation of dansyl amino acids and hydroxy acids by capillary electrochromatography and μ-high performance liquid chromatography. Electrophoresis 2001, 22:3339-3346.
104. Preinerstorfer B., Laemmerhofer M., Hoffmann C.V., Lubda D., Lindner W. Deconvolution of electrokinetic and chromatographic contributions to solute migration in stereoselective ion-exchange capillary electrochromatography on monolithic silica capillary columns. J. Sep. Sci. 2008, 31:3065-3078.
105. Chen Z., Hobo T. Chemically l-phenylalaninamide-modified monolithic silica column prepared by a sol-gel process for enantioseparation of dansyl amino acids by ligand exchange-capillary electrochromatography. Anal. Chem. 2001, 73:3348-3357.
106. Chen Z., Niitsuma M., Uchiyama K., Hobo T. Comparison of enantioseparations using Cu(II) complexes with l-amino acid amides as chiral selectors or chiral stationary phases by capillary electrophoresis, capillary electrochromatography and micro liquid chromatography. J. Chromatogr. A 2003, 990:75-82.
107. Chen Z., Nishiyama T., Uchiyama K., Hobo T. Electrochromatographic enantioseparation using chiral ligand exchange monolithic so-gel column. Anal. Chim. Acta 2004, 501:17-23.
108. Kang J., Wistuba D., Schurig V. A silica monolithic column prepared by the sol-gel process for enantiomeric separation by capillary electrochromatography. Electrophoresis 2002, 23:1116-1120.
109. Liu Z., Otsuka K., Terabe S., Motokawa M., Tanaka N. Physically adsorbed chiral stationary phase of avidin on monolithic silica column for capillary electrochromatography and capillary liquid chromatography. Electrophoresis 2002, 23:2973-2981.
110. Chen Z., Ozawa H., Uchiyama K., Hobo T. Cyclodextrin-modified monolithic columns for resolving dansyl amino acid enantiomers and positional isomers by capillary electrochromatography. Electrophoresis 2003, 24:2550-2558.
111. Preinerstorfer B., Lubda D., Mucha A., Kafarski P., Lindner W., Lammerhofer M. Stereoselective separations of chiral phosphinic acid pseudodipeptides by CEC using silica monoliths modified with an anion-exchange-type chiral selector. Electrophoresis 2006, 27:4312-4320.
112. Preinerstorfer B., Hoffmann C., Lubda D., Laemmerhofer M., Lindner W. Enantioselective silica-based monoliths modified with a novel aminosulfonic acid-derived strong cation exchanger for electrically driven and pressure-driven capillary chromatography. Electrophoresis 2008, 29:1626-1637.
113. Buchinger S., Follrich B., Laemmerhofer M., Lubda D., Lindner W. Chirally functionalized anion-exchange type silica monolith for enantiomer separation of 2-aryloxypropionic acid herbicides by non-aqueous capillary electrochromatography. Electrophoresis 2009, 30:3804-3813.
114. Messina A., Moroni S., Flieger M., Sinibaldi M., Ursini O. CEC enantioseparations of carboxylic acids on silica-based monoliths modified with ergot alkaloid derivative. Electrophoresis 2009, 30:2890-2896.
115. He C., Hendrickx A., Mangelings D., Smeyers-Verbeke J., Vander Heyden Y. Monolithic silica capillary columns with immobilized cellulose tris(3,5-dimethylphenylcarbamate) for enantiomer separations in CEC. Electrophoresis 2009, 30:3796-3803.
116. Ding G.-S., Tang A.-N. Capillary electrochromatographic separation of racemates on a norvancomycin-bonded monolithic column under reversed-phase conditions. J. Chromatogr. A 2008, 1208:232-238.
117. Tang A.-N., Wang X.-N., Ding G.-S., Yan X.-P. On-line preconcentration and enantioseparation of thalidomide racemates by CEC with the hyphenation of octyl and norvancomycin monoliths. Electrophoresis 2009, 30:682-688.
118. Kato M., Matsumoto N., Sakai-Kato K., Toyo'oka T. Investigation of chromatographic performances and binding characteristics of BSA-encapsulated capillary column prepared by the sol-gel method. J. Pharmaceut. Biomed. Anal. 2003, 30:1845-1850.
119. Kato M., Saruwatari H., Sakai-Kato K., Toyo'oka T. Silica sol-gel/organic hybrid material for protein encapsulated column of capillary electrochromatography. J. Chromatogr. A 2004, 1044:267-270.
120. Sakai-Kato K., Kato M., Nakakuki H., Toyo'oka T. Investigation of structure and enantioselectivity of BSA-encapsulated sol-gel columns prepared for capillary electrochromatography. J. Pharmaceut. Biomed. Anal. 2003, 31:299-309.
121. Hsieh M.-L., Li G.-Y., Chau L.-K., Hon Y.-S. Single-step approach to beta-cyclodextrin-bonded silica as monolithic stationary phases for CEC. J. Sep. Sci. 2008, 31:1819-1827.
122. Chankvetadze B., Yamamoto C., Tanaka N., Nakanishi K., Okamoto Y. High-performance liquid chromatographic enantioseparations on capillary columns containing monolithic silica modified with cellulose tris(3,5-dimethylphenylcarbamate). J. Sep. Sci. 2004, 27:905-911.
123. Chankvetadze B., Kubota T., Ikai T., Yamamoto C., Kamigaito M., Tanaka N., Nakanishi K., Okamoto Y. High-performance liquid chromatographic enantioseparations on capillary columns containing crosslinked polysaccharide phenylcarbamate derivatives attached to monolithic silica. J. Sep. Sci. 2006, 29:1988-1995.
124. Chankvetadze B., Ikai T., Yamamoto C., Okamoto Y. High-performance liquid chromatographic enantioseparations on monolithic silica columns containing a covalently attached 3,5-dimethylphenylcarbamate derivative of cellulose. J. Chromatogr. A 2004, 1042:55-60.
125. Kato M., Sakai-Kato K., Matsumoto N., Toyo'oka T. A protein-encapsulation technique by the sol-gel method for the preparation of monolithic columns for capillary electrochromatography. Anal. Chem. 2002, 74:1915-1921.
126. Zarbl E., Lammerhofer M., Woschek A., Hammerschmidt F., Parenti C., Cannazza G., Lindner W. Strong versus weak chiral cation exchangers: comparative evaluation for enantiomer separation of chiral bases by non-aqueous CEC. J. Sep. Sci. 2002, 25:1269-1283.
127. Karlsson C., Karlsson L., Armstrong D.W., Owens P.K. Evaluation of a vancomycin chiral stationary phase in capillary electrochromatography using polar organic and reversed-phase modes. Anal. Chem. 2000, 72:4394-4401.
128. Lin J.-M., Uchiyama K., Hobo T. Enantiomeric resolution of dansyl amino acids by capillary electrochromatography based on molecular imprinting method. Chromatographia 1996, 47:625-629.
129. Chirica G., Remcho V.T. Silicate entrapped columns. New columns designed for capillary electrochromatography. Electrophoresis 1999, 20:50-56.
130. Wistuba D., Schurig V. Enantiomer separation by capillary electrochromatography on a cyclodextrin-modified monolith. Electrophoresis 2000, 21:3152-3159.
131. Wistuba D., Banspach L., Schurig V. Enantiomeric separation by capillary electrochromatography using monolithic capillaries with sol-gel-glued cyclodextrin-modified silica particles. Electrophoresis 2005, 26:2019-2026.
132. Kato M., Dulay M.T., Bennett B., Chen J.-R., Zare R.N. Enantiomeric separation of amino acids and nonprotein amino acids using a particle-loaded monolithic column. Electrophoresis 2000, 21:3145-3151.
133. Schmid M.G., Koidl J., Freigassner C., Tahed S., Wojcik L., Beesley T., Armstrong D.W., Guebitz G. New particle-loaded monoliths for chiral capillary electrochromatographic separation. Electrophoresis 2004, 25:3195-3203.
134. Schmid M.G., Koidl J., Wank P., Kargl G., Zoehrer H., Guebitz G. Enantioseparation by ligand-exchange using particle-loaded monoliths: capillary-LC versus capillary electrochromatography. J. Biochem. Biophys. Methods 2007, 70:77-85.
135. Gatschelhofer C., Schmid M.G., Schreiner K., Pieber T.R., Sinner F.M., Guebitz G. Enantioseparation of glycyl-dipeptides by CEC using particle-loaded monoliths prepared by ring-opening metathesis polymerization (ROMP). J. Biochem. Biophys. Methods 2006, 69:67-77.
136. Lin J.-M., Nakagama T., Uchiyama K., Hobo T. Temperature effect on chiral recognition of some amino acids with molecularly imprinted polymer filled capillary electrochromatography. Biomed. Chromatogr. 1997, 11:298-302.
137. Lin J.-M., Nakagama T., Uchiyama K., Hobo T. Enantioseparation of d,l-phenylalanine by molecularly imprinted polymer particles filled capillary electrochromatography. J. Liq. Chromatogr. Relat. Technol. 1997, 20:1489-1506.
138. Wang H.-F., Zhu Y.-Z., Lin J.-P., Yan X.-P. Fabrication of molecularly imprinted hybrid monoliths via a room temperature ionic liquid-mediated nonhydrolytic sol-gel route for chiral separation of zolmitriptan by capillary electrochromatography. Electrophoresis 2008, 29:952-959.
139. Tan Z.J., Remcho V.T. Molecular imprint polymers as highly selective stationary phases for open tubular liquid chromatography and capillary electrochromatography. Electrophoresis 1998, 19:2055-2060.
140. Zaidi S.A., Cheong W.J. Robust open tubular layer of S-ketoprofen imprinted polymer for chiral LC separation. J. Sep. Sci. 2008, 31:2962-2970.
141. Zaidi S.A., Cheong W.J. Preparation of an open-tubular capillary column with a monolithic layer of S-ketoprofen imprinted and 4-styrenesulfonic acid incorporated polymer and its enhanced chiral separation performance in capillary electrochromatography. J. Chromatogr. A 2009, 1216:2947-2952.
142. Zaidi S.A., Han K.M., Hwang D.G., Cheong W.J. Preparation of open tubular molecule imprinted polymer capillary columns with various templates by a generalized procedure and their chiral and non-chiral separation performance in CEC. Electrophoresis 2010, 31:1019-1028.
143. Zaidi S.A., Han K.M., Sung Soon Kim D.G.H., Cheong W.J. Open tubular layer of S-ofloxacin imprinted polymer fabricated in silica capillary for chiral CEC separation. J. Sep. Sci. 2009, 32:996-1001.
144. Wang Y., Zeng Z., Guan N., Cheng J. Sol-gel technique for the preparation of beta-cyclodextrin derivative stationary phase in open-tubular capillary electrochromatography. Electrophoresis 2001, 22:2167-2172.