Locating regions of maximum chiral discrimination: A computational study of enantioselection on a popular chiral stationary phase used in chromatography

Journal of the American Chemical Society

Volumn 119, Issue 46, 1997, Pages 11269-11276

  Lipkowitz, Kenny B ^a   Coner, Robert ^a,b   Peterson, Michael A ^a,c  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c Box 117200 ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHYLBUTYRIC ACID; CYCLODEXTRIN; LIMONENE; MACROCYCLIC COMPOUND; PINENE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CHIRALITY; CHROMATOGRAPHY; DRUG PURIFICATION; ENANTIOMER; MOLECULAR RECOGNITION; TECHNIQUE; THEORY;

EID: 0030702922     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja972327e     Document Type: Article

References (83)

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6. For major reviews see: (a) Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27 (8), 1009. (b) Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27 (8), 89. (c) Rebek, J. Jr., Angew. Chem., Int. Ed. Engl. 1990, 29 (3), 245. (d) Schneider, H.-J. Angew. Chem., Int. Ed. Engl. 1991, 30, 1417. (e) Atwood, J. L.; Davies, J. E. D.; MacNirol, D. D.; Vögtle, F.; Lehn, J.-M.; Gokel, G. W., Eds. Comprehensive Supramolecular Chemistry, Pergamon Press: Oxford, 1996; especially Vols 1-3.
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10. (c) König, W. A. The Practice of Enantiomer Separation by Capillary Gas Chromatography; Hüthig: Heidelberg, 1987.
11. (d) Hinze, W. L.; Armstrong, D. W., Eds. Ordered Media in Chemical Separations; ACS Symp. Ser. No. 342; American Chemical Society: Washington, DC, 1987.
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14. (g) Chiral Liquid Chromatography; W. J., Lough, Ed. Blackie: London, 1989.
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19. For reviews see: (a) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (b) Martens, J.; Bhushan, R. Chem. Ztg. 1988, 112, 367. (c) Martens, J.; Bhushan, R. Int. J. Peptide Protein Res. 1989, 34, 433. (d) Martens, J.; Bhushan, R. J. Pharm. Biomed. Anal. 1990, 8, 259. (e) Bhushan, R.; Joshi, S. Biomed. Chromatogr. 1993, 7, 235.
20. For reviews see: (a) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (b) Martens, J.; Bhushan, R. Chem. Ztg. 1988, 112, 367. (c) Martens, J.; Bhushan, R. Int. J. Peptide Protein Res. 1989, 34, 433. (d) Martens, J.; Bhushan, R. J. Pharm. Biomed. Anal. 1990, 8, 259. (e) Bhushan, R.; Joshi, S. Biomed. Chromatogr. 1993, 7, 235.
21. For reviews see: (a) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (b) Martens, J.; Bhushan, R. Chem. Ztg. 1988, 112, 367. (c) Martens, J.; Bhushan, R. Int. J. Peptide Protein Res. 1989, 34, 433. (d) Martens, J.; Bhushan, R. J. Pharm. Biomed. Anal. 1990, 8, 259. (e) Bhushan, R.; Joshi, S. Biomed. Chromatogr. 1993, 7, 235.
22. For reviews see: (a) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (b) Martens, J.; Bhushan, R. Chem. Ztg. 1988, 112, 367. (c) Martens, J.; Bhushan, R. Int. J. Peptide Protein Res. 1989, 34, 433. (d) Martens, J.; Bhushan, R. J. Pharm. Biomed. Anal. 1990, 8, 259. (e) Bhushan, R.; Joshi, S. Biomed. Chromatogr. 1993, 7, 235.
23. For reviews see: (a) Ward, T. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (b) Martens, J.; Bhushan, R. Chem. Ztg. 1988, 112, 367. (c) Martens, J.; Bhushan, R. Int. J. Peptide Protein Res. 1989, 34, 433. (d) Martens, J.; Bhushan, R. J. Pharm. Biomed. Anal. 1990, 8, 259. (e) Bhushan, R.; Joshi, S. Biomed. Chromatogr. 1993, 7, 235.
24. Pertinent discussions can be found in ref 4; for additional reviews concerning gas chromatocraphic applications of cyclodextrins see: (a) König, W. A. In Drug Stereochemistry, Analytical Methods and Pharmacology; Wainer, I. W., Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 113-145. (b) Schurig, V.; Nowotny, H.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939. (c) Jung, M.; Mayer, S.; Schurig, V. LC-GC 1994, June, 458. (d) Mani, V.; Wooley, C. LC-GC 1995, Sept, 734.
25. Pertinent discussions can be found in ref 4; for additional reviews concerning gas chromatocraphic applications of cyclodextrins see: (a) König, W. A. In Drug Stereochemistry, Analytical Methods and Pharmacology; Wainer, I. W., Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 113-145. (b) Schurig, V.; Nowotny, H.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939. (c) Jung, M.; Mayer, S.; Schurig, V. LC-GC 1994, June, 458. (d) Mani, V.; Wooley, C. LC-GC 1995, Sept, 734.
26. Pertinent discussions can be found in ref 4; for additional reviews concerning gas chromatocraphic applications of cyclodextrins see: (a) König, W. A. In Drug Stereochemistry, Analytical Methods and Pharmacology; Wainer, I. W., Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 113-145. (b) Schurig, V.; Nowotny, H.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939. (c) Jung, M.; Mayer, S.; Schurig, V. LC-GC 1994, June, 458. (d) Mani, V.; Wooley, C. LC-GC 1995, Sept, 734.
27. Pertinent discussions can be found in ref 4; for additional reviews concerning gas chromatocraphic applications of cyclodextrins see: (a) König, W. A. In Drug Stereochemistry, Analytical Methods and Pharmacology; Wainer, I. W., Drayer, D. E., Eds.; Marcel Dekker: New York, 1988; pp 113-145. (b) Schurig, V.; Nowotny, H.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939. (c) Jung, M.; Mayer, S.; Schurig, V. LC-GC 1994, June, 458. (d) Mani, V.; Wooley, C. LC-GC 1995, Sept, 734.
28. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
29. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
30. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
31. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
32. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
33. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
34. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
35. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
36. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins in liquid chromatography see: (a) Armstrong, D. W.; Alak, A.; Bui, K.; DeMond, W.; Ward, T.; Riehl, T. E.; Hinze, W. L. J. Inclusion Phenom. 1984, 2, 533. (b) Armstrong, D. W. J. Liq. Chromatogr. 1984, 7, 353. (c) Beesley, T. E. Am. Lab. 1985, May, 78. (d) Ward, T. E.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 9, 407. (e) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (f) Johns, D. Am. Lab., 1987, January, 72. (g) Armstrong, D. W. Anal. Chem. 1987, 59, 84. (h) Pettersson, C. Trends Anal. Chem. 1988, 7, 209. (i) Armstrong, D. W.; Hilton, M.; Coffin, L. LC-GC 1991, Sept, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, Oct, 80.
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46. For reviews of molecular modeling applied to chiral chromatography see: (a) Lipkowitz, K. B. J. Chromatogr. A 1994, 666, 493. (b) Lipkowitz, K. B. J. Chromatogr. 1995, 694, 15. (c) Lipkowitz, K. B. In Theoretical and Computational Chemistry; Parkanyi, C., Ed.; Elsevier: New York, 1998; Vol. 5.
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68. This is a modified version of Kollman's original AMBER force field: Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C.; Alogona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765.
69. IRIS Explorer Center (North America), Downers Grove, IL 60551-5702 or via 〈URL http:/www.nag.co.uk/1h/Welcome_IEC〉.
70. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
71. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
72. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
73. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
74. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
75. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
76. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
77. Several groups have carried out limonene resolutions on this CSP including the following: (a) Schurig, V.; Nowotny, H.-P. J. Chromatogr. 1988, 441, 155. (b) Schurig, V.; Jung, M.; Schmalzing, D.; Schleimer, M.; Duvekot, J.; Buyten, J. C.; Peene, J. A.; Mussche, P. J. High Resolut. Chromatogr. 1990, 13, 470. (c) Takeoka, G.; Flath, R. A.; Mon, T. R.; Buttery, R. G.; Teranishi, R.; Güntert, M.; Lautamo, R.; Szejtli, J. J. High Resolut. Chromatogr. 1990, 13, 202. (d) Askari, C.; Hener, U.; Schmarr, H.-G.; Rapp, A.; Mosandl, A. Fresenius J. Anal. Chem. 1991, 340, 768. (e) Keim, W.; Köhnes, A.; Meltzow, W.; Römer, H. J. High Resolut. Chromatogr. 1991, 14, 507. (f) Mosandl, A.; Fischer, K.; Hener, U.; Kreis, P.; Rettinger, K.; Schubert, V.; Schmarr, H.-G. J. Agric. Food Chem. 1991, 39, 1131. (g) Bicchi, C.; Artuffo, G.; D'Amato, A.; Galli, A.; Galli, M. Chirality 1992, 4, 125. (h) Kobor, F.; Angermund, K.; Schomburg, G. J. High Resolut. Chromatogr. 1993, 16, 299.
78. Several groups have resolved pinene on this CSP, including all the citations in ref 20 and the following: Reinhardt, R.; Steinborn, A.; Engewald, W.; Anhalt, K.; Schulze, K. J. Chromatogr. A 1995, 697, 475.
79. Isomenthone: Askari, C.; Mosandl, A.; Schmarr, H.-G. Arch. Pharm. (Weinheim) 1992, 325, 35.
80. 1-Fluoro-1-phenylethane: Reinhardt, R.; Engewald, W.; Goj, O.; Haufe, G. Chromatographia 1994, 39, 192.
81. 1-Phenylethanol: see ref 20h.
82. Methylbutanol and Methylbutanoic acid: see ref 20f.
83. Bradshaw, J. S.; Chen, Z.; Yi, G.; Rossiter, B. E.; Malik, A.; Pyo, D.; Yun, H.; Black, D. R.; Zimmerman, S. S.; Lee, M. L.; Tong, W.; D'Souza, V. T. Anal. Chem. 1995, 67, 4437.