The Principle of Maximum Chiral Discrimination: Chiral Recognition in Permethyl-β-cyclodextrin

Journal of Organic Chemistry

Volumn 63, Issue 3, 1998, Pages 732-745

  Lipkowitz, Kenny B ^a   Coner, Robert ^a,b   Peterson, Michael A ^a,c   Morreale, Antonio ^a   Shackelford, Jason ^a  

^a INDIANA UNIVERSITY   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c UNIVERSITY OF FLORIDA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000648129     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9717090     Document Type: Article

References (76)

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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.
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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. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
24. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
25. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
26. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
27. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
28. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
29. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
30. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
31. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
32. Pertinent discussions can be found throughout ref 4; for additional reviews concerning applications of cyclodextrins 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. J.; Armstrong, D. W. J. Liq. Chromatogr. 1986, 5, 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, September, 646. (j) Husain, N.; Warner, I. M. Am. Lab. 1993, October, 80.
33. For reviews see: (a) Vespalec, R.; Bocek, P. Electrophoresis 1994, 15, 755. (b) Nishi, H.; Terabe, S. J. Chromatogr. A 1995, 694, 246. (c) Guttman, A.; Brunet, S.; Cooke, N. LC-GC 1996, January, 14, 32.
34. For reviews see: (a) Vespalec, R.; Bocek, P. Electrophoresis 1994, 15, 755. (b) Nishi, H.; Terabe, S. J. Chromatogr. A 1995, 694, 246. (c) Guttman, A.; Brunet, S.; Cooke, N. LC-GC 1996, January, 14, 32.
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37. Pertinent discussions can be found in ref 4; for additional reviews concerning applications of cyclodextrins in gas chromatography see: (a) Armstrong, D. W.; Han, S. CRC Crit. Rev. Anal. Chem. 1988, 19, 175. (b) 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. (c) Schurig, V.; Nowotny, H.-P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939. (d) Jung, M.; Mayer, S.; Schurig, V. LC-GC 1994, June, 458.
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74. ANOUT: written by M.A.P. to analyze MacroModel molecular dynamics trajectories. This software is available from Dr. Michael A. Peterson, Department of Chemistry, University of Florida, Gainesville, FL 32611.
75. IRIS Explorer Center (North America), Downers Grove, IL 60551-5702 or via 〈URL http://www.nag.co.uk/1h/Welcome_IEC〉.
76. MMODGRID: written by M.A.P. to calculate inter-molecular interaction energies along a grid using the AMBER* and MM3* force fields. This program is available from B. Coner: coner_bob@lilly.com. A parallel version, which uses the PVM library (PVM: Parallel Virtual Machine, MIT Press: Cambridge, 1994) is also available.