Chiral Recognition of Peptide Enantiomers by Cinchona Alkaloid Derived Chiral Selectors: Mechanistic Investigations by Liquid Chromatography, NMR Spectroscopy, and Molecular Modeling

Journal of Organic Chemistry

Volumn 68, Issue 22, 2003, Pages 8315-8327

  Czerwenka, Christoph ^a   Zhang, Mei Mei ^b   Kählig, Hanspeter ^a   Maier, Norbert M ^a   Lipkowitz, Kenny B ^b   Lindner, Wolfgang ^a  

^a UNIVERSITY OF VIENNA   (Austria)

^b NORTH DAKOTA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPLEXATION; CONFORMATIONS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE SEPARATION;

CHIRAL RECOGNITION;

CRYSTAL ORIENTATION;

ALANINE; CARBAMIC ACID DERIVATIVE; CINCHONA ALKALOID; CINCHONIDINE; DRUG DERIVATIVE; NITROBENZENE DERIVATIVE; OLIGOPEPTIDE; PEPTIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; ENANTIOSELECTIVITY; ENERGY; HYDROGEN BOND; LIQUID CHROMATOGRAPHY; METHODOLOGY; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; MOLECULAR MODEL; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEAR OVERHAUSER EFFECT; STEREOISOMERISM; THERMODYNAMICS;

ALANINE; CARBAMATES; CHROMATOGRAPHY, LIQUID; CINCHONA ALKALOIDS; DINITROBENZENES; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OLIGOPEPTIDES; PEPTIDES; STEREOISOMERISM; THERMODYNAMICS;

EID: 0142196894     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0346914     Document Type: Article

References (36)

1. Maier, N. M.; Franco, P.; Lindner, W. J. Chromatogr. A 2001, 906, 3-33.
2. Lämmerhofer, M.; Lindner, W. J. Chromatogr. A 1996, 741, 33-48.
3. Maier, N. M.; Nicoletti, L.; Lämmerhofer, M.; Lindner, W. Chirality 1999, 11, 522-528.
4. Mandl, A.; Nicoletti, L.; Lämmerhofer, M.; Lindner, W. J. Chromatogr. A 1999, 858, 1-11.
5. Czerwenka, C.; Lämmerhofer, M.; Maier, N. M.; Rissanen, K.; Lindner, W. Anal. Chem. 2002, 74, 5658-5666.
6. Piette, V.; Lämmerhofer, M.; Lindner, W.; Crommen, J. Chirality 1999, 11, 622-630.
7. Lämmerhofer, M.; Zarbl, E.; Lindner, W.; Simov, B. P.; Hammerschmidt, F. Electrophoresis 2001, 22, 1182-1187.
8. Czerwenka, C.; Lämmerhofer, M.; Lindner, W. Electrophoresis 2002, 23, 1887-1899.
9. Lämmerhofer, M.; Lindner, W. J. Chromatogr. A 1998, 829, 115-125.
10. Tobler, E.; Lämmerhofer, M.; Lindner, W. J. Chromatogr. A 2000, 875, 341-352.
11. Lämmerhofer, M.; Peters, E. C.; Yu, C.; Svec, F.; Fréchet, J. M. J.; Lindner, W. Anal. Chem. 2000, 72, 4623-4628.
12. Maier, N. M.; Schefzick, S.; Lombardo, G. M.; Feliz, M.; Rissanen, K.; Lindner, W.; Lipkowitz, K. B. J. Am. Chem. Soc. 2002, 124, 8611-8629.
13. Kano, K.; Hasegawa, H.; Miyamura, M. Chirality 2001, 13, 474-482.
14. Süß, F.; Kahle, C.; Holzgrabe, U.; Scriba, G. K. E. Electrophoresis 2002, 23, 1301-1307.
15. McEwen, I. Biopolymers 1993, 33, 933-942.
16. De Lorenzi, E.; Massolini, G.; Molinari, P.; Galbusera, C.; Longhi, R.; Marinzi, C.; Consonni, R.; Chiari, M. Electrophoresis 2001, 22, 1373-1384.
17. Marinzi, C.; Longhi, R.; Chiari, M.; Consonni, R. Electrophoresis 2001, 22, 3257-3262.
18. Tárkányi, G. J. Chromatogr. A 2002, 961, 257-276.
19. Yamamoto, C.; Yashima, E.; Okamoto, Y. J. Am. Chem. Soc. 2002, 124, 12583-12589.
20. Zhou, L.; Thompson, R.; Reamer, R. A.; Miller, C.; Welch, C.; Ellison, D. K.; Wyvratt, J. M. J. Chromatogr. A 2003, 987, 409-420.
21. Homer, J.; Perry, M. C. J. Chem. Soc., Faraday Trans. 1 1986, 82, 533-543.
22. Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1986, 108, 5627-5628.
23. Pirkle, W. H.; Pochapsky, T. C. J. Am. Chem. Soc. 1987, 109, 5975-5982.
24. Czernek, J. J. Phys. Chem. A 2003, 107, 3952-3959.
25. Peterson, M. A. Understanding Enantiodifferentiation Through Molecular Simulations, Ph.D. Thesis, Purdue University, 1996.
26. Feller, S. E.; Huster, D.; Gawrisch, K. J. Am. Chem. Soc. 1999, 121, 8963-8964.
27. Davis, A. L.; Laue, E. D.; Keeler, J.; Moskau, D.; Lohman, J. J. Magn. Reson. 1991, 94, 637-644.
28. Kay, E. L.; Keifer, P.; Saarinen, T. J. Am. Chem. Soc. 1992, 114, 10663-10665.
29. Schleucher, J.; Schwendinger, M.; Sattler, M.; Schmidt, P.; Schedletzky, O.; Glaser, S. J.; Sorensen, O. W.; Griesinger, C. J. Biomol. NMR 1994, 4, 301-306.
30. Böhlen, J. M.; Bodenhausen, G. J. Magn. Reson. A 1993, 102, 293-301.
31. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440-467.
32. Still, W. C.; Tempczyk, A.; Hawley, R. C.; Hendrickson, T. J. Am. Chem. Soc. 1990, 112, 6127-6129.
33. Leach, A. In Reviews in Computational Chemistry; Lipkowitz, K. B., Boyd, D. B., Eds.; VCH: Weinheim, Germany, 1991; Vol. 2, pp 1-47.
34. Gunsteren, W. F. v.; Berendsen, H. J. C. Mol. Simul. 1988, 1, 173-185.
35. Unpublished data.
36. Lipkowitz, K. B. Acc. Chem. Res. 2000, 33, 555-562.