High Efficiency Liquid and Super-/Subcritical Fluid-Based Enantiomeric Separations: An Overview

Journal of Liquid Chromatography and Related Technologies

Volumn 27, Issue 7-9, 2004, Pages 1121-1178

  Liu, Ying ^a   Lantz, Andrew W ^a   Armstrong, Daniel W ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Capillary electrochromatography (CEC); Capillary electrophoresis (CE); Chiral selectors; Chiral separations; Chiral stationary phases; Enantiomers; Liquid chromatography (LC); Supercritical fluid chromatography (SFC)

Indexed keywords

ELECTROPHORESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR STRUCTURE;

CHIRAL SELECTORS; LIGANDS;

SUPERCRITICAL FLUIDS;

ANALYTIC METHOD; CAPILLARY ELECTROPHORESIS; CHIRALITY; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MOLECULAR INTERACTION; REVIEW; SUPERCRITICAL FLUID CHROMATOGRAPHY;

EID: 2342559912     PISSN: 10826076     EISSN: None     Source Type: Journal    
DOI: 10.1081/JLC-120030600     Document Type: Review

References (241)

1. Jenner, P.; Testa, B. The influence of stereochemical factors on drug disposition. Drug. Metab. Rev. 1973, 2 (2), 117-184.
2. U.S. Food and Drug Administration. FDA's policy statement for the development of new stereoisomeric drugs. Chirality 1992, 4, 338-340.
3. Armstrong, D.W. Chiral stationary phases for high performance liquid chromatographic separation of enantiomers: a mini-review. J. Liq. Chromatogr. 1984, 7, 353-376.
4. Armstrong, D.W. Optical isomer separation by liquid chromatography. Anal. Chem. 1987, 59 (2), 84A-91A.
5. Rouhi, A.M. Chiral chemistry. Chem. Eng. News 2002, 80 (23), 43-50.
6. Armstrong, D.W.; Reid, G.L. III; Hilton, M.L.; Chang, C.D. Relevance of enantiomeric separations in environmental science. Environ. Pollut. 1993, 79 (1), 51-58.
7. Schneiderheinze, J.M.; Armstrong, D.W.; Berthod, A. Plant and soil enantioselective biodegradation of racemic phenoxyalkanoic herbicides. Chirality 1999, 11 (4), 330-337.
8. Armstrong, D.W.; Chang, C.D.; Li, W.Y. Relevance of enantiomeric separations in food and beverage analyses. J. Agric. Food. Chem. 1990, 38 (8), 1674-1677.
9. Ekborg-Ott, K.H.; Armstrong, D.W. Stereochemical analysis of food compounds. Chiral Separations 1997, 201-270.
10. Ward, T.J. Chiral separations. Anal. Chem. 2002, 74 (12), 2863-2872.
11. Phiney, K.W. SFC of Drug Enantiomers. Anal. Chem. 2000, 72 (5), 204A-211A.
12. Schurig, V. Separation of enantiomers by gas chromatography. J. Chromatogr. A 2001, 906 (1-2), 275-299.
13. Chankyetadze, B.; Blaschke, G. Enantioseparations in capillary electro-migration techniques: recent developments and future trends. J. Chromatogr. A 2001, 906 (1-2), 309-363.
14. Yashima, K. Polysaccharide-based chiral stationary phases for high-performance liquid chromatographic enantioseparation. J. Chromatogr. A 2001, 906 (1-2), 105-125.
15. Ward, T.J.; Farris, A.B., III. Chiral separations using the macrocyclic antibiotics: a review. J. Chromatogr. A 2001, 906 (1-2), 73-89.
16. Scriba, G.K.E. Pharmaceutical and biomedical applications of chiral capillary electrophoresis and capillary electrochromatography: an update. Electrophoresis 2003, 24 (15), 2409-2421.
17. Kang, J.; Wistuba, D.; Schurig, V. Recent progress in enantiomeric separation by capillary electrochromatography. Electrophoresis 2002, 23 (22-23), 4005-4021.
18. Armstrong, D.W. The evolution of chiral stationary phases for liquid chromatography. LC-GC. Curr. Issues in HPLC Technol. 1997, May, S20-S28.
19. Fanali, S. Enantioselective determination by capillary electrophoresis with cyclodextrins as chiral selectors. J. Chromatogr. A 2000, 875 (1+2), 89-122.
20. Pirke, W.H.; Finn, J.M.; Schreiner, J.L.; Hamper, B.C. A wide useful chiral stationary phase for the high-performance liquid chromatography separation of enantiomers. J. Am. Chem. Soc. 1981, 103 (13), 3964-3966.
21. Armstrong, D.W.; DeMond, W. Cyclodextrin bonded phases for the liquid chromatographic separation of optical, geometrical, and structural isomers. J. Chromatogr. Sci. 1984, 22, 411-415.
22. Allenmark, S.; Bomgren, B.; Borén, H. Direct liquid chromatographic separation of enantiomers on immobilized protein stationary phases: III. Optical resolution of a series of N-aroyl D, L-amino acids by high-performance liquid chromatography on bovine serum albumin covalently bound to silica. J. Chromatogr. 1983, 264, 63-68.
23. 1-acid glycoprotein as the chiral stationary phase. J. Chromatogr. 1983, 269, 71-80.
24. Armstrong, D.W.; Bertrand, G.L.; Ward, K.D.; Ward, T.J.; Secor, H.V.; Seeman, J.I. Evaluation of the effect of organic modifier and pH on retention and selectivity in reversed-phase liquid chromatographic separation of alkaloids on a cyclodextrin bonded phase. Anal. Chem. 1990, 62 (4), 332-338.
25. Stalcup, A.M.; Chang, S.C.; Armstrong, D.W. Effect of the configuration of the substituents derivatized beta-cyclodextrin bonded phases on enantioselectivity in normal phase liquid chromatography. J. Chromatogr. 1991, 540, 113-128.
26. Stalcup, A.M.; Chang, S.C.; Armstrong, D.W.; Pitha, J. (S)-2-hydroxyl-propyl-beta-cyclodextrin, a new chiral stationary phase for reversed-phase liquid chromatography. J. Chromatogr. 1990, 513, 181-194.
27. Armstrong, D.W.; Hilton, M.; Coffin, L. Multimodal chiral stationary phases for liquid chromatography: (R)-(S)-naphthylethyl-carbamate-derivatized β-cyclodextrin. LC-GC 1991, 9 (9), 646, 648-652.
28. Cyclobond Handbook, 6th Ed.; Advanced Separation Technology, Inc.: Whippany, NJ, 2002.
29. Armstrong, D.W.; Han, S.M.; Han, Y.I. Liquid chromatographic resolution of enantiomers containing single aromatic rings with beta-cyclodextrin-bonded phases. Anal. Chim. Acta 1988, 208, 275-281.
30. Armstrong, D.W.; Chang, X.; Chang, L.W.; Ibrahim, H.; Reid, G.R. III; Beesley, T.E. Comparison of the selectivity and retention of β-cyclodextrin vs. heptakis-2,3-O-dimethyl-β-cyclodextrin LC stationary phases for structural and geometric isomers. J. Liq. Chromatogr. Related Technol. 1997, 20 (20), 3279-3308.
31. Chang, S.C.; Reid, G.L. III; Chen, S.; Chang, C.D.; Armstrong, D.W. Evaluation of a new polar-organic high-performance liquid chromatographic mobile phase for cyclodextrin-bonded chiral stationary phases. Trends in Anal. Chem. 1993, 12 (4), 144-153.
32. Armstrong, D.W.; Chen, S.; Chang, C.; Chang, S. A new approach for the direct resolution of racernic beta adrenergic blocking agents by HPLC. J. Liq. Chromatogr. 1992, 15 (3), 545-556.
33. Ward, T.J.; Armstrong, D.W. Improved cyclodextrin chiral phases: a comparison and review. J. Liq. Chromatogr. 1986, 9, 407-423.
34. Armstrong, D.W. Optical isomer separation by liquid chromatography. Anal. Chem. 1987, 59, 84A-91A.
35. Gasper, M.P.; Berthod, A.; Nair, U.B.; Armstrong, D.W. Comparison and modeling study of vancomycin, ristocefin A, and teicoplanin for CE enantioseparations. Anal. Chem. 1996, 68, 2501-2514.
36. Armstrong, D.W.; Tang, Y.; Chen, S.; Zhou, Y.; Bagwill, C.; Chen, J. Macrocyclic antibiotics as a new class of chiral selectors for liquid chromatography. Anal. Chem. 1994, 66, 1473-1484.
37. Chirobiotic Handbook, 4th Ed.; Advanced Separations Technologies, Inc.: Whippany, NJ, 2002.
38. Armstrong, D.W.; Liu, Y.; Ekborg-Ott, K.H. A covalently bonded teicoplanin chiral stationary phases for HPLC enantioseparations. Chirality 1995, 7, 474-497.
39. Ekborg-Ott, K.H.; Liu, Y.; Armstrong, D.W. High enantioselective HPLC separations using the covalently bonded macrocyclic antibiotic, ristocetin A, chiral stationary phase. Chirality 1998, 10, 434-483.
40. Ekborg-Ott, K.H.; Wang, X.; Armstrong, D.W. Effect of selector cover-age and mobile phase composition on enantiomeric separations with ristocetin A chiral stationary phases. Microchem. J. 1999, 62, 26-49.
41. Berthod, A.; Liu, Y.; Bagwill, C.; Armstrong, D.W. Facile LC enantio-resolution of native amino acids and peptides using a teicoplanin chiral stationary phase. J. Chromatogr. A 1996, 731, 123-137.
42. Peter, A.; Torok, G.; Armstrong, D.W. High-performance liquid chromatographic separation of enantiomers of unusual amino acids on a teicoplanin chiral stationary phase. J. Chromatogr. A 1998, 793, 283-296.
43. Berthod, A.; Chen, X.; Kullman, J.P.; Armstrong, D.W.; Gasparrini, F.; D'Acquarica, I.; Villani, C.; Carotti, A. Role of the carbohydrate moieties in chiral recognition on teicoplanin-based LC stationary phases. Anal. Chem. 2000, 72, 1767-1780.
44. Xiao, T.L.; Rozhkov, R.V.; Larock, R.C.; Armstrong, D.W. Enantiomeric separation of substituted dihydrofurocoumarin compounds by HPLC using macrocyclic glycopeptide chiral stationary phases. Anal. Bioanal. Chem. 2003, 377, 639-654.
45. Chen, S.; Liu, Y.; Armstrong, D.W.; Borrell, JI; Martinez-Teipel, B.; Matallana, J.L. Enantioseparation of substituted 2-methoxy-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles on macrocyclic antibiotic and cyclo-dextrin stationary phases. J. Liq. Chromatogr. 1995, 18 (8), 1495-1507.
46. Kyba, E.P.; Siegel, M.G.; Sousa, L.R.; Sogah, G.D.Y.; Cram, D.J. Chiral, hinged, and functionalized multiheteromacrocycles. J. Am. Chem. Soc. 1973, 95 (8), 2691-2692.
47. Helgeson, R.C.; Timko, J.M.; Moreau, P.; Peacock, S.C.; Mayer, J.M.; Cram, D.J. Models for chiral recognition in molecular complexation. J. Am. Chem. Soc. 1974, 96 (21), 6762-6763.
48. Hyun, M.H.; Han, S.C.; Lipshutz, B.H.; Shin, Y.-J.; Welch, C.J. New chiral crown ether stationary phase for the liquid chromatographic resolution of α-amino acid enantiomers. J. Chromatogr. A 2001, 910, 359-365.
49. Nishi, H.; Nakamura, K.; Nakai, H.; Sato, T. Separation of enantiomers and isomers of amino compounds by capillary electrophoresis and high-performance liquid chromatography utilizing crown ethers. J. Chromatogr. A 1997, 757, 225-235.
50. Shinbo, T.; Yamaguchi, T.; Nishimura, K.; Sugiura, M. Chromatographic separation of racemic amino acids by use of chiral crown ether-coated reversed-phase packing. J. Chromatogr. 1987, 405, 145-153.
51. Okamoto, M.; Takahashi, K.I.; Doi, T. Direct stereochemical resolution of 3,4-dihydroxyphenylserine using a chiral crown ether stationary phase. J. Chromatogr. A 1994, 675, 244-247.
52. Peter, A.; Lazar, L.; Fulop, F.; Armstrong, D.W. High-performance liquid chromatographic enantioseparation of β-amino acids. J. Chromatogr. A 2001, 926, 229-238.
53. Behr, J.-P.; Girodeau, J.-M.; Hayward, R.C.; Lehn, J.-M.; Sauvage, J.-P. Molecular receptors. Functionalized and chiral macrocyclic polyethers derived from tartaric acid. Hel. Chim. Acta 1980, 63, 2096-2111.
54. Machida, Y.; Nishi, H.; Nakamura, K.; Nakai, H.; Sato, T. Enantiomer separation of amino compounds by a novel chiral stationary phase derived from crown ether. J. Chromatogr. A 1998, 805, 85-92.
55. Hyun, M.H. Characterization of liquid chromatographic chiral separation on chiral crown ether stationary phases. J. Sep. Sci. 2003, 26, 242-250.
56. Steffeck, R.J.; Zelechonok, Y.; Gahm, K.H. Enantioselective separation of racemic secondary amines on a chiral crown ether-based liquid chromatography stationary phase. J. Chromatogr. A 2002, 947, 301-305.
57. Hesse, G.; Hagel, R. Complete separation of a racemic mixture by elution chromatography on cellulose triacetate. Chromatographia 1973, 6 (6), 277-280.
58. Lindner, K.R.; Mannschreck, A. Separation of enantiomers by high-performance liquid chromatography on triacetylcellulose. J. Chromatogr. 1980, 193 (2), 308-310.
59. Blaschke, G. Chromatographic resolution of chiral drugs on polyamides and cellulose triacetate. J. Liq. Chromatogr. 1986, 9 (2-3), 341-368.
60. Okamoto, Y.; Kawashima, M.; Yamamoto, K.; 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, 5, 739-742.
61. Okamoto, Y.; Kawashima, M.; Hatada, K. Chromatographic resolution. 7. Useful chiral packing materials for high-performance liquid chromatographic resolution of enantiomers: phenylcarbamates of polysaccharides coated on silica gel. J. Am. Chem. Soc. 1984, 106 (18), 5357-5359.
62. Ichida, A.; Shibata, T.; Okamoto, I.; Yuki, Y.; Namikoshi, N.; Toga, Y. Resolution of enantiomers by HPLC on cellulose derivatives. Chromatographia 1984, 19, 280-294.
63. Tachibana, K.; Ohnishi, A. Reversed-phase liquid chromatographic separation of enantiomers on polysaccharide type chiral stationary phases. J. Chromatogr. A 2001, 906 (1-2), 127-154.
64. Okamoto, Y.; Yashima, E. Polysaccaride derivatives for chromatographic separation of enantiomers. Angew. Chem. Int. Ed. 1998, 37, 1020-1043.
65. Franco, P.; Senso, A.; Oliveros, L.; Minguillón, C. Covalently bonded polysaccharide derivatives as chiral stationary phases in high-performance liquid chromatography. J. Chromatogr. A 2001, 906 (1-2), 155-170.
66. Yashima, E.; Fukaya, H.; Okamoto, Y. (3,5-dimethylphenyl)carbamates of cellulose and amylose regioselectively bonded to silica gel as chiral stationary phases for high-performance liquid chromatography. J. Chromatogr. A 1994, 677 (1), 11-19.
67. Franco, P.; Senso, A.; Minguillón, C.; Oliveros, L. 3,5-dimethylphenyl-carbamates of amylose, chitosan and cellulose bonded on silica gel: comparison of their chiral recognition abilities as high-performance liquid chromatography chiral stationary, phases. J. Chromatogr. A 1998, 796, 265-272.
68. Oliveros, L.; López, P.; Minguillón, C.; Franco, P. Chiral chromatographic discrimination ability of a cellulose 3,5-dimethylphenylcarbamate/10-undercenoate mixed derivative fixed on several chromatographic matrixes. J. Liq. Chromatogr. 1995, 18 (8), 1521-1532.
69. Domenici, E.; Bertucci, C.; Salvadori, P.; Felix, G.; Cahagne, I.; Montellier, S.; Wainer, I.W. Synthesis and chromatographic properties of an HPLC chiral stationary phase based upon human serum albumin. Chromatographia 1990, 29 (3-4), 170-176.
70. Miwa, T.; Ichikawa, M.; Tsuno, M.; Hattori, T.; Miyakawa, T.; Kayano, M. ; Miyake, Y. Direct liquid chromatographic resolution of racemic compounds. Use of ovomucoid as a column ligand. Chem. Pharm. Bull. 1987, 35 (2), 682-686.
71. Miwa, T.; Miyakawa, T.; Miyake, Y. Characteristics of an avidin-conjugated column in direct liquid chromatographic resolution of racemic compounds. J. Chromatogr. 1988, 457, 227-233.
72. Erlandsson, P.; Marle, I.; Hansson, L.; Isaksson, R.; Petterson, G.; Petterson, C. Immobilized cellulase (CBH I) as a chiral stationary phase for direct resolution of enantiomers. J. Am. Chem. Soc. 1990, 112 (11), 4573-4574.
73. Haginaka, J.; Miyano, Y.; Saizen, Y.; Seyama, C.; Murashima, T. Separation of enantiomers on a pepsin-bonded column. J. Chromatogr. A 1995, 708, 161-168.
74. Mano, N.; Oda, Y.; Miwa, T.; Asakawa, N.; Yoshida, Y.; Sato, T. Conalbumin-conjugated silica gel, a new chiral stationary phase for high performance liquid chromatography. J. Chromatogr. 1992, 603 (1-2), 105-109.
75. Massolini, G.; De Lorenzi, E.; Lloyd, D.K.; McGann, A.M.; Caccialanza, G. Evaluation of β-lactoglobulin as a stationary phase in high-performance liquid chromatography and as a buffer additive in capillary electrophoresis: observation of a surprising lack of stereoselectivity. J. Chromatogr. B 1998, 712 (1+2), 83-94.
76. Marle, I.; Erlandsson, P.; Hansson, L.; Isaksson, R.; Pettersson, C.; Pettersson, G. Separation of enantiomers using cellulase (CBH I) silica as a chiral stationary phase. J. Chromatogr. 1991, 586, 233-248.
77. Erlandsson, P.; Nilsson, S. Use of a fragment of bovine serum albumin as chiral stationary phase in liquid chromatography. J. Chromatogr. 1990, 482, 35-51.
78. Pinkerton, T.C.; Howe, W.J.; Ulrich, E.L.; Comiskey, J.P.; Haginaka, J.; Murashima, T.; Walkenhorst, W.F.; Westler, W.M.; Markley, J.L. Protein binding chiral discrimination of HPLC stationary phases made with whole, fragmented, and third domain turkey ovomucoid. Anal. Chem. 1995, 67, 2354-2367.
79. Haginaka, J. Protein-based chiral stationary phases for high-performance liquid chromatography enantioseparations. J. Chromatogr. A 2001, 906 (1-2), 253-273.
80. Okamoto, Y.; Suzuki, K.; Ohta, K.; Hatada, K.; Yuki, H. Optically active poly(triphenylmethyl methacrylate) with one-handed helical confirmation. J. Am. Chem. Soc. 1979, 101 (16), 4763-4765.
81. Yuki, H.; Okamoto, Y.; Okamoto, I. Resolution of racemic compounds by optically active poly(triphenylmethyl methacrylate). J. Am. Chem. Soc. 1980, 102 (20), 6356-6358.
82. Okamoto, Y.; Honda, S.; Okamoto, I.; Yuki, H.; Murata, S.; Noyori, R.; Takaya, H. Novel packing material for optical resolution: (+)-poly(triphenylmethyl methacrylate) coated on macroporous silica gel. J. Am. Chem. Soc. 1981, 103 (23), 6971-6973.
83. Okamoto, Y.; Nakano, T. Asymmetric polymerization. Chem. Rev. 1994, 94 (2), 349-372.
84. Okamoto, Y.; Hatada, K. Resolution of enantiomers by HPLC on optically active poly(triphenylmethyl methacrylate). J. Liq. Chromatogr. 1986, 9 (2-3), 369-384.
85. Nakano, T. Optically active synthetic polymers as chiral stationary phases in HPLC. J. Chromatogr. A 2001, 906, 205-225.
86. Okamoto, Y.; Mohri, H.; Hatada, K. Chromatographic optical resolution by optically active poly(diphenyl-2-pyridylmethyl methacrylate) with a highly one-handed helical structure. Polym. J. (Tokyo, Japan) 1989, 21 (5), 439-445.
87. Nakano, T.; Matsuda, A.; Mori, M.; Okamoto, Y. Asymmetric anionic polymerization of 1-phenyldibenzosuberyl and 1-(2-pyridyl)dibenzosuberyl methacrylates and chiral recognition ability of the obtained polymers. Polym. J. (Tokyo, Japan) 1996, 28 (4), 330-336.
88. Nakano, T.; Satoh, Y.; Okamoto, Y. Asymmetric polymerization of 1-(3-pyridyl)dibenzosuberyl methacrylate and chiral recognition by the obtained optically active polymer having single-handed helical confirmation. Polym. J. (Tokyo, Japan) 1998, 30 (8), 635-640.
89. Wulff, G. Molecular imprinting in crosslinked materials with the aid of molecular templates-a way towards artificial antibodies. Angew. Chem. Int. Ed. Engl. 1995, 34 (17), 1812-1832.
90. Remcho, V.T.; Tan, Z.J. MIPs as chromatographic stationary phases for molecular recognition. Anal. Chem. 1999, 71 (7), 248A-255A.
91. Takeuchi, T.; Haginaka, J. Separation and sensing based on molecular recognition using molecularly imprinted polymers. J. Chromatogr. B 1999, 728 (1), 1-20.
92. Vidyasankar, S.; Ru, M.; Arnold, F.H. Molecularly imprinted ligand-exchange adsorbents for the chiral separation of underivatized amino acids. J. Chromatogr. A 1997, 775, 51-63.
93. Ramström, O., Ye, L.; Gustavsson, P.E. Chiral recognition by molecularly imprinted polymers in aqueous media. Chromatographia 1998, 48 (3/4), 197-202.
94. Klemm, L.H.; Reed, D. Optical resolution by molecular complexation chromatography. J. Chromatogr. 1960, 3, 364-368.
95. Mikes, F.; Boshart, G.; Gil-Av, E. Resolution of optical isomers by high-performance liquid chromatography, using coated and bonded chiral charge-transfer complexing agents as stationary phases. J. Chromatogr. 1976, 122, 205-221.
96. Mikes, F.; Boshart, G. Resolution of optical isomers by high-performance liquid chromatography: a comparison of two selector-selectand systems. J. Chromatogr. 1978, 149, 455-464.
97. Mikes, F.; Boshart, G. Binaphthyl-2,2′-diyl hydrogen phosphate. A new chiral atropisomeric selector for the resolution of helicenes using high performance liquid chromatography. Chem. Commun. 1978, 4, 173-175.
98. Gasparrini, F.; Misiti, D.; Villani, C. High-performance liquid chromatography chiral stationary phases based on low-molecular-mass selectors. J. Chromatogr. A 2001, 906, 35-50.
99. Welch, C.J. Evolution of chiral stationary phase design in the Pirkle laboratories. J. Chromatogr. A 1994, 666, 3-26.
100. Hyun, M.H.; Min, C.S. Unusual high enantioselectivity by a new HPLC chiral stationary phase. Tetrahedron Lett. 1997, 38 (11), 1943-1946.
101. Hyun, M.H.; Kang, M.H.; Han, S.C. Liquid chromatographic resolution of 2-hydroxycarboxylic acids on a new chiral stationary phase derived from (S)-leucine. J. Chromatogr. A 2000, 868 (1), 31-39.
102. Pirkle, W.H.; Murray, P.G.; Wilson, S.R. X-ray crystallographic evidence in support of a proposed chiral recognition mechanism. J. Org. Chem. 1996, 61 (14), 4775-4777.
103. Pirkle, W.H.; Welch, C.J.; Lamm, B. Design, synthesis, and evaluation of an improved enantioselective naproxen selecor. J. Org. Chem. 1992, 57 (14), 3854-3860.
104. Oi, N.; Nagase, M.; Inda, Y.; Doi, T. High-performance liquid chromatographic separation of enantiomers on (S)-2-(4-chlorophenyl)isovaleric acid and its amide derivatives bonded to silica gel. J. Chromatogr. 1983, 265 (1), 111-116.
105. Pirkle, W.H.; Liu, Y. On the relevance of face-edge π-π interactions to chiral recognition. J. Chromatogr. A 1996, 749, 19-24.
106. Lin, C.-E.; Lin, C.-H.; Li, F.-K. Enantioseparation of amino acids and amino alcohols on chiral stationary phases derived from α-amino acid- and pyrrolidinyl-disubstituted cyanuric chloride. J. Chromatogr. A 1996, 722, 189.
107. Lin, C.-E.; Li, F.-K. Enantioseparation and recognition mechanisms of dinitrobenzoyl-derivatized amino acids and amino alcohols on chiral stationary phases consisting of cyanuric chloride with (S or R)-phenylalanyl-(S or R)-1-(1-naphthyl)ethylamide substituent. J. Chromatogr. A 1996, 722, 199-209.
108. Machida, Y.; Nishi, H.; Nakamura, K.; Nakai, H.; Sato, T. Enantiomeric separation of diols and β-amino alcohols by chiral stationary phase derived form (R,R)-tartramide. J. Chromatogr. A 1997, 757, 73-79.
109. Vaton-Chanvrier, L.; Peulon, V.; Combret, Y.; Combret, J.C. Synthesis, characterization, and enantioselectivity of cholic acid-bonded phases for high performance liquid chromatography. Chromatographia 1997, 46 (11/12), 613-622.
110. Iuliano, A.; Salvadori, P.; Felix, G. Synthesis of a new family of four deoxycholic acid derived chiral stationary phases and their evaluation in the HPLC resolution of racermic compounds. Tetrahedron: Asymmetry 1999, 10 (17), 3353-3364.
111. Messina, A.; Girelli, A.M.; Flieger, M.; Sinibaldi, M.; Sedmera, P.; Cvak, L. Direct resolution of optically active isomers on chiral packings containing ergoline skeletons. 5. Enantioseparation of amino acid derivatives. Anal. Chem. 1996, 68, 1191-1196.
112. Davankov, V.A.; Rogozhin, S.V. Ligand chromatography as a novel method for the investigation of mixed complexes: stereoselective effects in α-amino acid copper (II) complexes. J. Chromatogr. 1971, 60, 284-312.
113. Davankov, V.A.; Rogozhin, S.V.; Semechkin, A.V.; Sachkova, T.P. Ligand-exchange chromatography of racemates: influence of the degree of saturation of the asymmetric resin by metal ions on ligand exchange. J. Chromatogr. 1973, 82, 359-365.
114. Roumeliotis, P.; Unger, K.K.; Kurganov, A.A.; Davankov, V.A. High-performance ligand-exchange chromatography of α-amino acid enantiomers: studies on monomerically bonded 3-(L-prolyl)- and 3-(L-hydroxyprolyl)propyl silicas. J. Chromatogr. 1983, 255, 51-66.
115. + silicas on retention and enantioselectivity of α-amino acids in high-performance liquid chromatography. J. Chromatogr. 1983, 266, 439-450.
116. Hare, P.E.; Gil-Av, E. Separation of D and L amino acids by liquid chromatography: use of chiral eluants. Science 1979, 204 (4398), 1226-1228.
117. Gil-Ac, E.; Tishbee, A.; Hare, P.E. Resolution of underivatized amino acids by reversed-phase chromatography. J. Am. Chem. Soc. 1980, 102 (15), 5115-5117.
118. Kurganov, A. Chiral chromatographic separations based on ligand exchange. J. Chromatogr. A 2001, 906, 51-57.
119. Davankov, V.A. 30 years of chiral ligand exchange. Enantiomer 2000, 5 (3-4), 209-223.
120. Śliwka, M.; Ślebioda, M.; Kolodziejczyk, A.M. Dynamic ligand-exchange chiral stationary phases derived from N-substituted (S)-phenylglycinol selectors. J. Chromatogr. A 1998, 824, 7-14.
121. Yoshida, A.; Kuroda, K.; Kurauchi, Y.; Inoue, T.; Ohga, K. N-(1(l-carboxyalkyl) chitosan as a chiral selector. Kichin, Kitosan Kenkyu 1999, 5 (2), 188-189.
122. 2 separations of enantiomers on a broadly applicable polysiloxane chiral stationary phase. J. Chromatogr. A 1996, 753 (1), 109-119.
123. Wolf, C.; Pirkle, W.H. Synthesis and evaluations of a copolymeric chiral stationary phase. J. Chromatogr. A 1998, 799 (1+2), 177-184.
124. Mandl, A.; Nicoletti, L.; Lammerhofer, M.; 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.
125. Schmalzing, D.; Nichlson, G.J.; Jung, M.; Schurig, V. Enantiomer separation by capillary SFC and GC on immobilized permethyl-β-cyclodextrin: a systematic comparison. J. Micro. Sep. 1992, 4 (1), 23-28.
126. Armstrong, D.W.; Tang, Y.; Ward, T.; Nichols, M. Derivatized cyclo-dextrins immobilized on fused-silica capillaries for enantiomeric separations via capillary electrophoresis, gas chromatography, or supercritical fluid chromatography. Anal. Chem. 1993, 65, 1114-1117.
127. Schurig, V.; Jung, M.; Mayer, S.; Fluck, M.; Negura, S.; Jakubetz, H. Unified enantioselective capillary chromatography on a chirasil-DEX stationary phase advantages of column miniaturization. J. Chromatogr. A 1995, 694, 119-128.
128. Röeder, W.; Ruffing, F.-J.; Schomburg, G.; Pirkle, W.H. Chiral SFC-separations using polymer-coated open tubular fused silica columns. Comparison of enantiomeric selectivity in SFC and LC using the same stationary phase of the Pirkle type. J. High Resolut. Chromatogr. 1987, 10 (12), 665-667.
129. Mourier, P.A.; Eliot, E.; Caude, M.; Rosset, R.; Tambute, A. Supercritical and subcritical fluid chromatography on a chiral stationary phase for the resolution of phosphine oxide enantiomers. Anal. Chem. 1985, 57 (14), 2819-2823.
130. Whatley, J. Enantiomeric separation by packed column chiral supercritical fluid chromatography. J. Chromatogr. A 1995, 697, 251-255.
131. Gyllenhaal, O.; Karlsson, A.; Vessman, J. Applications of packed column supercritical fluid chromatography in the development of dmgs drugs. Chromatographic Science Series 1998, 75 (Supercritical Fluid Chromatography with Packed Columns), 273-300.
132. Anton, K.; Siffrin, C. Packed-column SFC in the pharmaceutical industry: CGMP aspects. Analusis 1999, 27 (8), 691-701.
133. Williams, K.L.; Sander, L.C. Enantiomer separations on chiral stationary phases in supercritical fluid chromatography. J. Chromatogr. A 1997, 785, 149-158.
134. Berger, T.A. Packed Column SFC; Royal Society of Chemistry: Cambridge, 1995.
135. Berger, T.A.; Smith, J.; Fogelman, K.; Kruluts, K. Semipreparative chiral separations using supercritical fluid chromatography with stacked injections. Am. Lab. 2002, 34 (21), 14-20.
136. Macaudiere, P.; Caude, M.; Rosset, R.; Tambute, A. Resolution of racemic amides and phosphine oxide on a β-cylcodextrin-bonded stationary phase by subcritical fluid chromatography. J. Chromatogr. 1987, 405, 135-143.
137. Macaudiere, P.; Caude, M.; Rosset, R.; Tambute, A. Chiral resolutions in SFC: mechanisms and applications with various chiral stationary phases. J. Chromatogr. Sci. 1989, 27 (10), 583-591.
138. Williams, K.L.; Sander, L.C.; Wise, S.A. Use of a naphthyethylcarbamoylated-β-cyclodextrin chiral stationary phase for the separation of drug enantiomers and related compounds by sub- and supercritical fluid chromatography. Chirality 1996, 8 (4), 325-331.
139. Williams, K.L.; Sander, L.C.; Wise, S.A. Comparison of liquid and supercritical fluid chromatography using naphthylethylcarbamoylated-β -cyclodextrin chiral stationary phase. J. Chromatogr. A 1996, 746 (1), 91-101.
140. Dönnecke, J.; Svensson, L.A.; Gyllenhaal, O.; Karlsson, K.-E.; Karlsson, A.; Vessman, J. Evaluation of a vancomycin chiral stationary phase in packed capillary supercritical fluid chromatography. J. Microcol. Sep. 1999, 11 (7), 521-533.
141. Toribio, L.; David, F.; Sandra, P. Enantiomeric separation of some cyclic ketones and dioxalene derivatives by chiral SFC. Quim. Anal. 1999, 18, 269-273.
142. Svensson, L.A.; Ovens, P.K. Enantioselective supercritical fluid chromatography using ristocetin A chiral stationary phases. Analyst 2000, 125, 1037-1039.
143. Medvedovici, A.; Sandra, P.; Toribio, L.; David, F. Chiral packed column subcritical fluid chromatography on polysaccharide and macrocyclic antibiotic chiral stationary phases. J. Chromatogr. A 1997, 785, 159-171.
144. Liu, Y.; Rozhkov, R.; Larock, R.C.; Xiao, T.L.; Armstrong, D.W. Fast super/subcritical fluid chromatography enantiomeric separations of dihydrofurocoumarin derivatives with macrocyclic glycopeptide stationary phases. Chromatographia 2003, 58, 775-779.
145. Liu, Y.; Berthod, A.; Metchell, C.R.; Xiao, T.L.; Zhang, B. Super/subcritical fluid chromatography chiral separations with macrocyclic glycopeptide stationary phases. J. Chromatogr. A 2002, 978, 185-204.
146. Thienpont, A.; Gal, J.; Aeschlimann, C.; Felix, G. Studies on stereo-selective separations of the "azole" antifungal drugs ketoconazole and itraconazole using HPLC and SFC on silica-based polysaccharides. Analusis 1999, 27 (8), 713-718.
147. Bernal, J.L.; Toribio, L.; del Nozal, M.J.; Nieto, E.M.; Montequi, M.I. Separation of antifungal chiral drugs by SFC and HPLC: a comparative study. J. Biochem. Biophys. Meth. 2002, 54, 245-254.
148. Biermanns, P.; Miller, C.; Lyon, V.; Wilson, W. Chiral resolution of β-blockers by packed-column supercritical fluid chromatography. LC-GC 1993, 11 (10), 744-747.
149. Bargmann-Leyder, N.; Tambuté, A.; Caude, M. A comparison of LC and SFC for cellulose- and amylose-derived chiral stationary phases. Chirality 1995, 7 (5), 311-325.
150. Yaku, K.; Aoe, K.; Nishimura, N.; Sato, T.; Morishita, F. Chiral resolution of four optical isomers of diltiazem hydrochloride on Chiralcel columns by packed-column supercritical fluid chromatography. J. Chromatogr. A 1997, 785, 185-193.
151. Smith, R.M.; Ma, L. Chiral supercritical fluid chromatography of phenylpropropanols and related compounds. J. Chromatogr. A 1997, 785, 179-184.
152. del Nozal, M.J.; Toribio, L.; Bernal, J.L.; Nieto, E.M.; Jiménez, J.J. Separation of albendazole sulfoxide enantiomers by chiral supercritical-fluid chromatography. J. Biochem. Biophys. Meth. 2002, 54, 339-345.
153. Williams, K.L.; Sander, L.C.; Wise, S.A. Comparison of liquid and supercritical fluid chromatography for the separation of enantiomers on chiral stationary phases. J. Pharm. Biomed. Anal. 1997, 15 (11), 1789-1799.
154. Blum, A.M.; Lynam, K.G.; Nicolas, E.C. Use of a new Pirkle-type chiral stationary phase in analytical and preparative subcritical fluid chromatography of pharmaceutical compounds. Chirality 1994, 6 (4), 302-313.
155. Terfloth, G.J.; Pirkle, W.H.; Lynam, K.G.; Nicolas, E.C. Broadly applicable polysiloxane-based chiral stationary phase for high-performance liquid chromatography and supercritical fluid chromatography. J. Chromatogr. A 1995, 705 (2), 185-194.
156. Bargmann-Leyder, N.; Thiebaut, D.; Vergne, F.; Begos, A.; Tambute, A.; Caude, M. High-speed chiral separation of β-blockers by supercritical fluid chromatography on ChyRoSine-A. Chromatographia 1994, 39 (11/12), 673-681.
157. Schurig, V.; Fluck, M. Enantiomer separation by complexation. SFC on immobilized chirasil-nickel and chirasil-zinc. J. Biochem. Biophys. Meth. 2000, 43 (1-3), 223-240.
158. Johannsen, M. Separation of enantiomers of ibuprofen on chiral stationary phases by packed column supercritical fluid chromatography. J. Chromatogr. A 2001, 937, 135-138.
159. Wu, Y. Investigational Study on Enantiomeric Separation of Pharmaceutical Compounds Using Supercritical and Subcritical Fluid Ion-Pairing Chromatography, Book of Abstracts, 219th ACS National Meeting, San Francisco, CA, March 2000.
160. Petersen, M. Packed columns in supercritical fluid chromatography. J. Chromatogr. 1990, 505, 3-18.
161. Lee, C.R.; Porziemsky, J.-P.; Aubert, M.-C.; Krstulovic, A.M. Liquid and high-pressure carbon dioxide chromatography of β-blockers: resolution of the enantiomers of nadolol. J. Chromatogr. 1991, 539, 55-69.
162. Anton, K.; Eppinger, J.; Frederiksen, L.; Francotte, E.; Berger, T.A.; Wilson, W.H. Chiral separations by packed-column super- and subcritical fluid chromatography. J. Chromatogr. A 1994, 666, 395-401.
163. Camilleri, P. Separation of enantiomers. In Capillary Electrophoresis: Theory and Practice, 2nd Ed.; CRC Press: Boca Raton, FL, 1998; 183-247.
164. Schmitt, U.; Branch, S.K.; Holzgrabe, U. Chiral separations by cyclodextrin-modified capillary electrophoresis-determination of the enantiomeric excess. J. Sep. Sci. 2002, 25, 959-974.
165. Wren, S. The use of cyclodextrins as chiral selectors. Chromatographia 2001, 54, S59-S77.
166. Vespalec, R.; Bocek, P. Chiral separations in capillary electrophoresis. Chem. Rev. 2000, 100, 3715-3753.
167. Lurie, I.S. Separation selectivity in chiral and achiral capillary electrophoresis with mixed cyclodextrins. J. Chromatogr. A 1997, 792, 297-307.
168. Marina, M.L.; Crego, A.L. Capillary electrophoresis: a good alternative for the separation of chiral compounds of environmental interest. J. Liq. Chromatogr. & Rel. Technol. 1997, 20, 1337-1365.
169. Furuta, R.; Doi, T. Chiral separation of diniconazole, uniconazole and structurally related compounds by cyclodextrin-modified micellar capillary electrophoresis. Electrophoresis 1994, 15, 1322-1325.
170. Valkó, I.E.; Billiet, H.A.H.; Frank, J.; Luyben, K.Ch.A.M. Effect of the degree of substitution of (2-hydroxy)propyl-β-cyclodextrin on the enantioseparation of organic acids by capillary electrophoresis. J. Chromatogr. A 1994, 678, 139-144.
171. Ueda, T.; Mitchell, R.; Kitamura, F.; Metcalf, T. Separation of naphthalene-2,3-dicarboxaldheyde-labeled amino acids by high performance capillary electrophoresis with laser-induced fluorescence detection. J. Chromatogr. 1992, 593, 265-274.
172. Yoshinaga, M.; Tanaka, M. Use of selectively methylated β-cyclodextrin in chiral separations of dansylamino acids by capillary zone electrophoresis. J. Chromatogr. A 1994, 679, 359-365.
173. Gahm, K.; Stalcup, A.M. Capillary zone electrophoresis study of naphthylethylcarbamoylated β-cyclodextrins. Anal. Chem. 1995, 67, 19-25.
174. Fanali, S.; Aturki, Z. Use of cyclodextrins in capillary electrophoresis for the chiral resolution of some 2-arylpropionic acid non-steroidal anti-inflammatory drugs. J. Chromatogr. A 1995, 694, 297-305.
175. Egger, M.D.; Liu, Y.; Sevcik, J.; Tesarova, E.; Rozhkov, R.; Larock, R.C.; Armstrong, D.W. Enantioseparation of dihydrofurocoumarin derivatives by various separation modes of capillary electrophoresis. Electrophoresis 2003, 24, 2650-2656.
176. Pharr, D.Y.; Fu, Z.S.; Smith, T.K.; Hinze, W.L. Solubilization of cyclodextrins for analytical applications. Anal. Chem. 1989, 61, 275-279.
177. Hinze, W.L.; Pharr, D.Y.; Fu, Z.S.; Burkert, W.G. Thin-layer chromatography with urea solubilized β-cyclodextrin mobile phases. Anal. Chem. 1989, 61, 422-428.
178. Yoshinaga, M.; Tanaka, M. Effect of urea addition on chiral separation of dansylamino acids by capillary zone electrophoresis with cyclodextrins. J. Chromatogr. A 1995, 710, 331-337.
179. Salvador, A.; Varesio, E.; Dreux, M.; Veuthey, J. Binding constant dependency of amphetamines with various commercial methylated β-cyclodextrins. Electrophoresis 1999, 20, 2670-2679.
180. Schmitt, T.; Engelhardt, H. Charged and uncharged cyclodextrins as chiral selectors in capillary electrophoresis. Chromatographia 1993, 37, 475-481.
181. Kuhn, R.; Erni, F.; Bereuter, T.; Häusler, J. Chiral recognition and enantiomeric resolution based on host-guest complexation with crown ethers in capillary electrophoresis. Anal. Chem. 1992, 64, 2815-2820.
182. Kuhn, R. Enantiomeric separation by capillary electrophoresis using a crown ether as chiral selector. Electrophoresis 1999, 20, 2605-2613.
183. Kuhn, R.; Wagner, J.; Walbroehl, Y.; Bereuter, T. Potential and limitations of an optically active crown ether for chiral separation in capillary zone electrophoresis. Electrophoresis 1994, 15, 828-834.
184. Walbroehl, Y.; Wagner, J. Chiral separations of amino acids by capillary electrophoresis and high-performance liquid chromatography employing chiral crown ethers. J. Chromatogr. A 1994, 685, 321-329.
185. Schmid, M.G.; Gübitz, G. Capillary zone electrophoretic separation of the enantiomers of dipeptides based on host-guest complexation with a chiral crown ether. J. Chromatogr. A 1995, 709, 81-88.
186. Kuhn, R.; Stoecklin, F.; Erni, F. Chiral separations by host-guest complexation with cyclodextrin and crown ether in capillary electrophoresis. Chromatographia 1992, 33, 32-36.
187. Dutton, P.J.; Fyles, T.M.; McDermid, S. Synthesis and metal-ion complexation behavior of polycarboxylate 18-crown-6 ethers derived from tartaric acid. Can. J. Chem. 1988, 66, 1097-1108.
188. Behr, J.P.; Lehn, J.M.; Vierling, P. Molecular receptors. Structural effects and substrate recognition in binding of organic and biogenic ammonium ions by chiral polyfunctional macrocyclic polyethers bearing amino acid and other side-chains. Helv. Chim. Acta 1982, 65, 1853-1867.
189. Jang, J.; Cho, S. II; Chung, D. Comparative studies of various run buffers for chiral capillary electrophoresis using chiral crown ether as a chiral selector. Electrophoresis 2001, 22, 4362-4367.
190. Armstrong, D.W.; Chang, L.W.; Chang, S.S.C. Mechanism of capillary electrophoresis enantioseparations using a combination of an achiral crown ether plus cyclodextrins. J. Chromatogr. A 1998, 793, 115-134.
191. Kuhn, R.; Steinmetz, C.; Bereuter, T.; Haas, P.; Erni, F. Enantiomeric separation in capillary zone electrophoresis using chiral crown ether. J. Chromatogr. A 1994, 666, 367-373.
192. Desiderio, C.; Fanali, S. Chiral analysis by capillary electrophoresis using antibiotics as chiral selector. J. Chromatogr. A 1998, 807, 37-56.
193. Aboul-Enein, H.Y.; Ali, I. Macrocyclic antibiotics as effective chiral selectors for enantiomeric resolution by liquid chromatography and capillary electrophoresis. Chromatographia 2000, 52, 679-691.
194. Armstrong, D.W.; Gasper, M.P.; Rundlett, K.L. Highly enantioselective capillary electrophoretic separations with dilute solution of the macrocyclic antibiotic ristocetin A. J. Chromatogr. A 1995, 689, 285-304.
195. Ward, T.J.; Dann, C. III; Blaylock, A. Enantiomeric resolution using the macrocyclic antibiotics rifamycin B and rifamycin SV as chiral selectors for capillary electrophoresis. J. Chromatogr. A 1995, 715, 337-344.
196. Rundlett, K.L.; Gasper, M.P.; Zhou, E.Y.; Armstrong, D.W. Capillary electrophoretic enantiomeric separations using the glycopeptide antibiotic, teicoplanin. Chirality 1996, 8, 88-107.
197. Armstrong, D.W.; Rundlett, K.; Reid, G.L. III. Use of a Macrocyclic antibiotic, rifamycin B, and indirect detection for the resolution of racemic amino alcohols by CE. Anal. Chem. 1994, 66, 1690-1695.
198. Vespalec, R.; Billiet, H.A.H.; Frank, J.; Bocek, P. Vancomycin as a chiral selector in capillary electrophoresis: an appraisal of advantages and limitations. Electrophoresis 1996, 17, 1214-1221.
199. Rundlett, K.L.; Armstrong, D.W. Effect of micelles and mixed micelles on efficiency and selectivity of antibiotic-based capillary electrophoretic enantioseparations. Anal. Chem. 1995, 67, 2088-2095.
200. Armstrong, D.W.; Seguin, R.; Fendler, J.H. Partitioning of amino acids and nucleotides between water and micellar hexadecyltrimethylammonium halides. The prebiotic significance of cationic surfaces. J. Molec. Evol. 1977, 10, 241-250.
201. Armstrong, D.W.; Terrill, R.Q. Thin layer chromatographic separation of pesticides, decachlorobiphenyl, and nucleosides with micellar solutions. Anal. Chem. 1979, 51, 2160-2163.
202. Armstrong, D.W.; Henry, S.J. Use of an aqueous micellar mobile phase for separation of phenols and polynuclear aromatic hydrocarbons via HPLC. J. Liq. Chromatogr. 1980, 3, 657-662.
203. Armstrong, D.W. Pseudophase liquid chromatography: applications to TLC. J. Liq. Chromatogr. 1980, 3, 895-900.
204. Armstrong, D.W.; Nome, F. Partitioning behavior of solutes eluted with micellar mobile phases in liquid chromatography. Anal. Chem. 1981, 53, 1662-1666.
205. Terabe, S.; Otsuka, K.; Ichikawa, K.; Tsuchiya, A.; Ando, T. Electrokinetic separations with micellar solutions and open-tubular capillaries. Anal. Chem. 1984, 56, 111-113.
206. Shamsi, S.A.; Warner, I.M. Monomeric and polymeric chiral surfactants as pseudo-stationary phases for chiral separations. Electrophoresis 1997, 18, 853-872.
207. Bjørnsdottir, I.; Honoré Hansen, S.; Terabe, S. Chiral separation in non-aqueous media by capillary electrophoresis using the ion-pair principle. J. Chromatogr. A 1996, 745, 37-44.
208. Terabe, S.; Shibata, M.; Miyashita, Y. Chiral separation by electrokinetic chromatography with bile salt micelles. J. Chromatogr. 1989, 480, 403-411.
209. Nishi, H.; Fukuyama, T.; Matsuo, M. Chiral separation of diltiazem, trimetoquinol and related compounds by micellar electrokinetic chromatography with bile salts. J. Chromatogr. 1990, 515, 233-243.
210. Otsuka, K.; Terabe, S. Enantiomeric resolution by micellar electrokinetic chromatography with chiral surfactants. J. Chromatogr. 1990, 515, 221-226.
211. Mazzeo, J.R.; Grover, E.R.; Swartz, M.E.; Petersen, J.S. Noval chiral surfactant for the separation of enantiomers by micellar electrokinetic capillary chromatography. J. Chromatogr. A 1994, 680, 125-135.
212. Dobashi, A.; Hamada, M.; Dobashi, Y. Enantiomeric separation with sodium dodecanoyl-L-amino acidate micelles and poly(sodium(10-undecenoyl)-L-valinate) by electrokinetic chromatography. Anal. Chem. 1995, 67, 3011-3017.
213. Tickle, D.C.; Okafo, G.N.; Camilleri, P.; Jones, R.F.D.; Kirby, A. Glucopyranoside-based surfactants as pseudostationary phases for chiral separations in capillary electrophoresis. Anal. Chem. 1994, 66, 4121-4126.
214. Dobashi, A.; Ono, T.; Hara, S.; Yamaguchi, J. Optical resolution of enantiomers with chiral mixed micelles by electrokinetic chromatography. Anal. Chem. 1989, 61, 1986-1988.
215. Wang, J.; Warner, I.M. Chiral separations using micellar electrokinetic capillary chromatography and a polymerized chiral micelle. Anal. Chem. 1994, 66, 3773-3776.
216. Paleos, C.M.; Stassinopoulou, C.I.; Malliaris, A. Comparative studies between monomeric and polymeric sodium 10-undecenoate micelles. J. Phys. Chem. 1983, 87, 251-254.
217. Agnew-Heard, K.A.; Pena, M.S.; Shamsi, S.A.; Warner, I.M. Studies of polymerized sodium N-undecylenyl-L-valinate in chiral micellar electrokinetic capillary chromatography of neutral, acidic, and basic compounds. Anal. Chem. 1997, 69, 985-964.
218. D'Hulst, A.; Verbeke, N. Chiral separation by capillary electrophoresis with oligosaccharides. J. Chromatogr. 1992, 608, 275-287.
219. D'Hulst, A.; Verbeke, N. Separation of the enantiomers of coumarinic anticoagulant drugs by capillary electrophoresis using maltodextrins as chiral modifiers. Chirality 1994, 6, 225-229.
220. Kano, K.; Minami, K.; Horiguchi, K.; Ishimura, Ta.; Kodera, M. Ability of non-cyclic oligosaccharides to form molecular complexes and its use for chiral separation by capillary zone electrophoresis. J. Chromatogr. A 1995, 694, 307-313.
221. Nishi, H. Enantiomer separation of basic drugs by capillary electrophoresis using ionic and neutral polysaccharides as chiral selectors. J. Chromatogr. A 1996, 735, 345.
222. Stalcup, A.P.; Agyel, N.M. Heparin: a chiral mobile-phase additive for capillary zone electrophoresis. Anal. Chem. 1994, 66, 3054-3059.
223. Jin, Y.; Stalcup, A.M. Application of heparin to chiral separations of antihistamines by capillary electrophoresis. Electrophoresis 1998, 19, 2119-2123.
224. Wang, X.; Lee, J.; Armstrong, D.W. Separation of enantiomers by capillary electrophoresis using pentosan polysulfate. Electrophoresis 1999, 20, 162-170.
225. Chankvetadze, B.; Saito, M.; Yashima, E.; Okamoto, Y. Enantioseparation using selected polysaccharides as chiral buffer additives in capillary electrophoresis. J. Chromatogr. A 1997, 773, 331-338.
226. Rundle, R.E.; Foster, J.F.; Baldwin, R.R. The nature of the starch-iodine complex. J. Am. Chem. Soc. 1944, 66, 2116-2120.
227. Busch, S.; Kraak, J.C.; Poppe, H. Chiral separations by complexation with proteins in capillary zone electrophoresis. J. Chromatogr. 1993, 635, 119-126
228. Ishihama, Y.; Oda, Y.; Asakawa, N.; Yoshida, Y.; Sato, T. Optical resolution by electrokinetic chromatography using ovomucoid as a pseudo-stationary phase. J. Chromatogr. A 1994, 666, 193-201.
229. Matsunaga, H.; Haginaka, J. Separation of basic drug enantiomers by capillary electrophoresis using ovoglycoprotein as a chiral selector: comparison of chiral resolution ability of ovoglycoprotein and completely deglycosylated ovoglycoprotein. Electrophoresis 2001, 22, 3251-3256.
230. Valtcheva, L.; Mohammad, J.; Pettersson, G.; Hjertén, S. Chiral separation of β-blockers by high-performance capillary electrophoresis based on non-immobilized cellulase as enantioselective protein. J. Chromatogr. 1993, 638, 263-267.
231. Lloyd, D.K.; Aubry, A.; De Lorenzi, E. Selectivity in capillary electrophoresis: the use of proteins. J. Chromatogr. A 1997, 792, 349-369.
232. Haginaka, J. Enantiomer separation of drugs by capillary electrophoresis using proteins as chiral selectors. J. Chromatogr. A 2000, 875, 235-254.
233. Hage, D.S. Chiral separations in capillary electrophoresis using proteins as stereoselective binding agents. Electrophoresis 1997, 18, 2311-2321.
234. Li, S.; Lloyd, D.K. Direct chiral separations by capillary electrophoresis using capillaries packed with an α1-acid glycoprotein chiral stationary phase. Anal. Chem. 1993, 65, 3684-3690.
235. Li, S.; Lloyd, D.K. Packed-capillary electrochromatographic separation of the enantiomers of neutral and anionic compounds using β-cyclodextrin as a chiral selector. Effect of operating parameters and comparison with free-solution capillary electrophoresis. J. Chromatogr. A 1994, 666, 321, 321-335.
236. Meyer, S.; Schurig, V. Enantiomer separation using mobile and immobile cyclodextrin derivatives with electromigration. Electrophoresis 1994, 15, 835-841.
237. Schurig, V.; Wistuba, D. Recent innovations in enantiomer separation by electrochromatography utilizing modified cyclodextrins as stationary phases. Electrophoresis 1999, 20, 2313-2328.
238. Francotte, E.; Jung, M. Enantiomer separation by open-tubular liquid chromatography and electrochromatography in cellulose-coated capillaries. Chromatographia 1996, 42, 521-527.
239. Karlsson, C.; Wikström, H.; Armstrong, D.W.; Owens, P.K. Enantio-selective reversed-phase and non-aqueous capillary electrochromatography using teicoplanin chiral stationary phase. J. Chromatogr. A 2000, 897, 349-363.
240. Karlsson, C.; Karlsson, K.; 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.
241. Desbène, P.L.; Fulchic, C.E. Utilization of N-alkyl-β -D-glucopyranosides in enantiomeric separation by micellar electrokinetic chromatography. J. Chromatogr. A 1996, 749, 257-269.