α-peptide/β-peptoid chimeras

Organic Letters

Volumn 9, Issue 8, 2007, Pages 1549-1552

  Olsen, Christian A ^a   Bonke, Gitte ^a   Vedel, Line ^a   Adsersen, Anne ^a   Witt, Matthias ^b   Franzyk, Henrik ^a   Jaroszewski, Jerzy W ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b BRUKER DALTONIK GMBH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; PEPTIDE; PEPTOID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; DRUG EFFECT; MICROBIAL VIABILITY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CIRCULAR DICHROISM; MICROBIAL VIABILITY; MOLECULAR STRUCTURE; PEPTIDES; PEPTOIDS;

EID: 34247466045     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070316c     Document Type: Article

References (34)

1. Tossi, A.; Sandri, L.; Giangaspero, A. Biopolymers 2000, 55, 4-30.
2. Zasloff, M. Nature 2002, 415, 389-395.
3. Mygind, P. H.; Fischer, R. L.; Schnorr, K. M.; Hansen, M. T.; Sönksen, C. P.; Ludvigsen, S.; Raventós, D.; Buskov, S.; Christiensen, B.; De Maria, L.; Taboureau, O.; Yaver, D.; Elvig- Jørgensen, S. G.; Sørensen, M. V.; Christensen, B. E.; Kjærulff, S.; Frimodt-Møller, N.; Lehrer, R. I.; Zasloff, M.; Kristensen, H.-H. Nature 2005, 437, 975-980.
4. Matsuzaki, K. Biochem. Biophys. Acta 1999, 1462, 1-10.
5. Shai, Y. Biochem. Biophvs. Acta 1999, 7462, 55-70.
6. Yang, L.; Weiss, T. M.; Lehrer, R. I.; Huang, H. W. Biophys. J. 2000, 79, 2002-2009.
7. Pujals, S.; Fernández-Carneado, J.; López-Iglesias, C.; Kogan, M. J.; Giralt, E. Biochem. Biophys. Acta 2006, 1758, 264-279.
8. Hilpert, K.; Volkmer-Engert, R.; Walter, T.; Hancock, R. E. W. Nat. Biotechnol. 2005, 23, 1008-1012.
9. Gellman, S. H. Acc. Chem. Res. 1998, 31, 173-180.
10. Hill, D. J.; Mio, M. J.; Prince, R. B.; Hughes, T. S.; Moore, J. S. Chem. Rev. 2001, 101, 3893-4011.
11. (a) Cheng, R. P.; Gellman, S. H.; DeGrado, W. F. Chem. Rev. 2001, 101, 3219-3232.
12. (b) Seebach, D.; Beck, A. K.; Bierbaum, D. J. Chem. Biodiv. 2004, 1, 1111-1239.
13. Kirshenbaum, K.; Barron, A. E.; Goldsmith, R. A.; Armand, P.; Bradley, E. K.; Truong, K. T. V.; Dill, K. A.; Cohen, F. E.; Zuckermann, R. N. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 4303-4308.
14. Zasloff, M. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 5449-5453.
15. Arvidsson, P. I.; Ryder, N. S.; Weiss, H. M.; Hook, D. F.; Escalante, J.; Seebach, D. Chem. Biodiv. 2005, 2, 401-420.
16. Hamuro, Y.; Schneider, J. P.; DeGrado, W. F. J. Am. Chem. Soc. 1999, 121, 12200-12201.
17. Porter, E. A.; Wang, X.; Lee, H.-S.; Weisblum, B.; Gellman, S. H. Nature 2000, 404, 565. Erratum: Nature 2000, 405, 298.
18. Patch, J. A.; Barron, A. E. J. Am. Chem. Soc. 2003, 125, 12092-12093.
19. Violette, A.; Fournel, S.; Lamour, K.; Chaloin, O.; Frisch, B.; Briand, J.-P.; Monteil, H.; Guichard, G. Chem. Biol. 2006, 13, 531-538.
20. Tew, G. N.; Liu, D.; Chen, B.; Doerksen, R. J.; Kaplan, J.; Carroll, P. J.; Klein, M. L.; DeGrado, W. F. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 5110-5114.
21. Shuey, S. W.; Delaney, W. J.; Shah, M. C.; Scialdone, M. A. Bioorg. Med. Chem. Lett. 2006, 16, 1245-1248.
22. Fernandez-Lopez, S.; Kim, H.-S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, 452-456.
23. Norgren, A. S.; Zhang, S.; Arvidsson, P. I. Org. Lett. 2006, 8, 4533-4536.
24. De Pol, S.; Zorn, C.; Klein, C. D.; Zerbe, O.; Reiser, O. Angew. Chem., Int. Ed. 2004, 43, 511-514.
25. Hayen, A.; Schmitt, M. A.; Ngassa, F. N.; Thomasson, K. A.; Gellman, S. H. Angew. Chem., Int. Ed. 2004, 43, 505-511.
26. Schmitt, M. A.; Weisblum, B.; Gellman, S. H. J. Am. Chem. Soc. 2004, 126, 6848-6849.
27. Sanborn, T. J.; Wu, C. W.; Zuckermann, R. N.; Barron, A. E. Kopolymers 2002, 63, 12-20.
28. See the Supporting Information (Figure SI) for normalized CD spectra of 12 and 13 in various solvents.
29. Appella, D. H.; Christianson, L. A.; Klein, D. A.; Powell, D. R.; Huang, X.; Barchi, J. J., Jr.; Gellman, S. H. Nature 1997, 387, 381-384.
30. Hart, S. A.; Bahadoor, A. B. F.; Matthews, E. E.; Qiu, X. J.; Schepartz, A. J. Am. Chem. Soc. 2003, 125, 4022-4023.
31. For examples, see: (a) Kojima, S.; Kuriki, Y.; Sato, Y.; Arisaka, F.; Kumagai, I.; Takahashi, S.; Miura, K.-i. Biochem. Biophys. Acta 1996, 1294, 129-137.
32. (b) Smith, J. S.; Scholtz, J. M. Biochemistry 1998, 37, 33-40.
33. Thus far, structural investigations of the synthesized oligomers by NOESY and ROESY experiments proved fruitless due to signal overlap. Hence, efforts to prepare analogues suitable for NMR spectroscopic investigation have been initiated.
34. Glättli, A.; Daura, X.; Seebach, D.; van Gunsteren, W. F. J. Am. Chem. Soc. 2002, 124, 12972-12978.