Fluorine in Peptides: Coiled coil model systems as tools to evaluate the influence of fluorinated amino acids on structure and stability of peptides

Chimica Oggi

Volumn 25, Issue 4, 2007, Pages 48-53

  Hakelberg, Matthias ^b   Koksch, Beate ^a  

^a FREIE UNIVERSITÄT BERLIN   (Germany)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34548293041     PISSN: 0392839X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (35)

1. W. Zhang, Curr. Opin Drug Discov. Devel. 7, 784-797 (2004).
2. S. Dandapani, QSAR Comb. Sci. 25, 681-688 (2006).
3. H. Glatz, C. Blay, H. Engelhardt, W. Bannwarth, Chromatographia 59, 567-570 (2004).
4. M. P. Krafft, "Applications of fluorous compounds in materials chemistry." in Handbook of Fluorous Chemistry J A Gladysz, D. P. Curran, I. T. Horvath, Eds.; Wiley-VCH, 2004, 478-490.
5. H.-J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, M. Stahl, ChemBioChem 5, 637-643 (2004).
6. A. Bondi, J. Phys. Chem. 68, 441-451 (1964).
7. B. K. Park, N. R. Kitteringham, P. M. O'Neill, Annu. Rev. Pharmacol. Toxicol. 41, 443-70 (2001).
8. G. R. Desiraju, Acc. Chem. Res. 35, 565-573 (2002).
9. Jack D. Dunitz, ChemBioChem 5, 614-621 (2004).
10. C. Jäckel, B. Koksch, Eur. J. Org. Chem. 21, 4471-4477 (2005).
11. R. E. Connor, D. A. Tirrell, Polymer Reviews 47, 9-28 (2007).
12. W. D. Kohn, R. S. Hodges, Trends Biotechnol. 16, 379-389 (1998).
13. M. O. Steinmetz, I. Jelesarov, W. M. Matousek, S. Honnappa, W. Jahnke, J. H. Missimer, S. Frank, A. T. Alexandrescu, R A. Kammerer, Proc. Natl. Acad. Sci. USA 104, 7062-7067 (2007).
14. F. H. S. Crick, Acta Crystallogr. 6, 689-697 (1953).
15. J. M. Mason, K. M. Arndt, ChemBioChem 5, 170-176 (2004).
16. Y. Tang, G. Ghirlanda, N. Vaidehi, J. Kua, D. T. Mainz, W. A. Goddard III, W. F. DeGrado, D. A. Tirrell, Biochemistry 40, 2790-2796 (2001).
17. E.K. O'Shea, J.D. Klemm, P.S. Kim, and T. Alber, Science 25, 539-544 (1991).
18. Y. Tang, G. Ghirlanda, W. A. Petka, T. Nakajima, W. F. DeGrado, D. A. Tirrell, Angew. Chem. In t. Ed. 40, 1494-1496 (2001).
19. Y. Tang, D. A. Tirrell, J. Am. Chem. Soc 123, 11089-11090 (2001).
20. W. A. Petka, J. L. Harden, K. P. McGrath, D. Wirtz, D. A. Tirrell, Science 281, 389-392 (1998).
21. S. Son, I. C. Tanrikulu, D. A. Tirrell, ChemBioChem 7, 1251-1257 (2006).
22. A. Acharya, S. B. Ruvinov, J. Gal, J. R. Moll, C. Vinson, Biochemistry 41, 14122-14131 (2002).
23. B. Bilgicer, A. Fichera, K. Kumar, J. Am. Chem. Soc. 123, 4393-4399 (2001).
24. N. C. Yoder, K. Kumar, Chem. Soc. Rev. 31, 335-341 (2002).
25. B. Bilgiçer, X. Xing, K. Kumar, J. Am. Chem. Soc. 123, 11815-11816 (2001).
26. B. Bilgiçer, K. Kumar, Tetrahedron 58, 4105-4112 (2002).
27. B. Bilgiçer, K. Kumar, Proc. Natl. Acad. Sci USA 101, 15324-15329 (2004).
28. K.-H. Lee, H.-Y. Lee, M. M. Slutsky, J. T. Anderson, E. N. G. Marsh, Biochemistry 43, 16277-16284 (2004).
29. H.-Y. Lee, K.-H. Lee, H. M. Al-Hashim, E. N. G. Marsh, J. Am. Chem. Soc. 128, 337-343 (2006).
30. C. Jäckel, W. Seufert, S. Thust, B. Koksch, ChemBioChem 5, 717-720 (2004).
31. C. Jäckel, M. Salwiczek, B. Koksch, Angew. Chem. Int. Ed. 45, 4198-4203 (2006).
32. M. Salwiczek, C. Jäckel, B. Koksch, "Molecular Interactions of Fluorinated Amino Acids in a Native Polypeptide Environment" in: Fluorine & Health, G. Haufe, A. Tressaud Eds.; Elsevier, in press.
33. K. Pagel, K. Seeger, B. Seiwert, A. Villa, A. E. Mark, S. Berger and B. Koksch, Org. Biomol. Chem. 3, 1189-1194 (2005).
34. B. E. Smart, J. Fluorine Chem. 109, 3-11 (2001).
35. K. Severin, D. H. Lee, A. J. Kennan, M. R. Ghadiri, Nature 389, 706-709 (1997).