Comparison of cyclodextrin-dipeptide inclusion complexes in the absence and presence of urea by means of capillary electrophoresis, nuclear magnetic resonance and molecular modeling

European Journal of Organic Chemistry

Volumn , Issue 18, 2007, Pages 2921-2930

  Waibel, Benjamin ^a   Scheiber, Josef ^a   Meier, Claudia ^a   Hammitzsch, Manuela ^b   Baumann, Knut ^c   Scriba, Gerhard K E ^b   Holzgrabe, Ulrike ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

^c TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

Capillary electrophoresis; Cyclodextrin complex; Dipeptides; Molecular dynamics simulations

Indexed keywords

EID: 34347348327     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700052     Document Type: Article

References (45)

1. J. Li, K. G. Waldron, Electrophoresis 1999, 20, 171-179.
2. S. Sabah, G. K. E. Scriba, J. Chromatogr. A 1999, 833, 261-266.
3. S. Sabah, G. K. E. Scriba, J. Chromatogr. A 2000, 894, 267-272.
4. G. K. E. Scriba, Electrophoresis 2003, 24, 4063-4077.
5. S. Sabah, G. K. E. Scriba, Electrophoresis 2001, 22, 1385-1393.
6. F. Süß, C. E. Sänger-van de Griend, G. K. E. Scriba, Electrophoresis 2003, 24, 1069-1076.
7. F. Süß, W. Poppitz, G. K. E. Scriba, J. Sep. Sci. 2002, 25, 1147-1154.
8. N. Sidamonidze, F. Süß, W. Poppitz, G. K. E. Scriba, J. Sep. Sci. 2001, 24, 777-783.
9. S. Sabbah, F. Süß, G. K. E. Scriba, Electrophoresis 2001, 22, 3163-3170.
10. A. M. Rizzi, L. Kremser, Electrophoresis 1999, 20, 2715-2722.
11. A. Rizzi, Electrophoresis 2001, 22, 3079-3106.
12. F. Süß, C. Kahle, U. Holzgrabe, G. K. E. Scriba. Electrophoresis 2002, 23, 1301-1307.
13. a) H. J. Schneider, F. Hacket, V. Rüdiger, Chem. Rev. 1998, 98, 1755-1785;
14. b) B. Chankvetadze, G. Blaschke, G. Pintore, In: NMR spectroscopy in Drug Development and analysis, VCH-Wiley, Weinheim, 1999; chapter 10, pp. 154-173.
15. G. Hembury, M. Rekharsky, A. Nakamura, Y. Inoue, Org. Lett. 2000, 2, 3257-3260.
16. M. V. Rekahrsky, Y. Inoue, J. Am. Chem. Soc. 2002, 124, 813-826.
17. a) M. V. Rekahrsky, H. Yamamura, M. Kawai, Y. Inoue, J. Org. Chem. 2003, 68, 5228-5235;
18. b) J. R. Garbow, J. J. Likos, S. A. Schroeder, J. Agric. Food Chem. 2001, 49, 2053-2060;
19. c) K. Miyake, F. Hirayama, K. Uekama, J. Pharm. Sci. 1999, 88, 39-45.
20. C. Kahle, R. Deubner, C. Schollmayer, J. Scheiber, K. Baumann, U. Holzgrabe, Eur. J. Org. Chem. 2005, 8, 1578-1589.
21. a) S. Terabe, J. Pharm. Biomed. Anal. 1992, 10, 705-715;
22. b) A. Amini, U. Paulsen Sörman, B. H. Lindgren, D. Westerlund, Electrophoresis 1998, 19, 731-737.
23. K. D. Altria, B. J. Clark, P.-E. Mahuzier, Chromatographia 2000, 52, 758-768.
24. J. L. Clark, J. J. Stezowski, J. Am. Chem. Soc. 2001, 123, 9880-9888.
25. J. M. Alexander, J. L. Clark, T. J. Brett, J. J. Stezowski, Proc. Natl. Acad. Sci. USA 2002, 99, 5115-5120.
26. M. Yoshingaga, M. Tanaka, J. Chromatogr. A 1995, 710, 331-337.
27. a) T. Carofiglio, R. Fornasier, L. Jicsinszky, G. Saielli, U. Tonellato, R. Vetta, Eur. J. Org. Chem. 2002, 7, 1191-1196;
28. b) B. Chankvetadze, Chem. Soc. Rev. 2004, 33, 337-347;
29. c) H. Dodziuk, W. Kozminski, A. Ejchart, Chirality 2004, 16, 90-105;
30. d) C. Hellriegel, H. Händel, M. Wedig, S. Steinhauer, F. Sörgel, K. Albert, U. Holzgrabe, J. Chromatogr. A 2001, 914, 315-324.
31. P. K. Glasoe, F. A. Long, J. Phys. Chem. 1960, 64, 188-190.
32. M. Bodanszky, A. Bodanszky, The Practice of Peptide Synthesis, 2nd ed., Springer-Verlag,, Berlin 1994, p. 110.
33. J. M. Martínez, L. Martíne, J. Comput. Chem. 2003, 24, 819-825.
34. J. M. Alexander, J. L. Clark, T. J. Brett, J. J. Stezowski, Proc. Natl. Acad. Sci. USA 2002, 99, 5115-5120.
35. F. H. Allen, Acta Crystallogr., Sect. B 2002, 58, 380-388.
36. http://www.accelrys.com/dstudio/ds_viewer/Accelrys, San Diego, CA, USA.
37. http://openbabel.sourceforge.net/
38. L. Kalé, R. Skeel, M. Bhandarkar, R. Brunner, A. Gursoy, N. Krawetz, J. Phillips, A. Shinozaki, K. Varadarajan, K. Schulten, J. Comput. Phys. 1999, 151, 283-312.
39. http://www.ks.uiuc.edu/Research/namd
40. A. Pedretti, L. Villa, G. Vistoli, J. Mol. Graph. 2002, 21, 47-49.
41. A. Pedretti, L. Villa, G. Vistoli, J. Comput. Aided Mol. Des. 2004, 18, 167-173.
42. http://www.ddl.unimi.it
43. B. R. Brooks, R. E. Bruccoleri, B. D. Olafson, D. J. States, S. Swaminathan, M. Karplus, J. Comput. Chem. 1983, 4, 187-217.
44. The Mathworks Inc., Natick, MA, USA.
45. http://www.ks.uiuc.edu/Development/MDTools/matdcd/