Efficient microwave-assisted synthesis of multivalent dendrimeric peptides using cycloaddition reaction (click) chemistry

Chemical Communications

Volumn , Issue 36, 2005, Pages 4581-4583

  Rijkers, Dirk T S ^a   Van Esse, G Wilma ^a   Merkx, Remco ^a   Brouwer, Arwin J ^a   Jacobs, Hans J F ^a   Pieters, Roland J ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; AZIDE; DENDRIMER; LIGAND; PEPTIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; CYCLOADDITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; MICROWAVE RADIATION; PURIFICATION; SYNTHESIS;

EID: 26444556393     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b507975f     Document Type: Article

References (38)

1. M. Mammen, S.-K. Choi and G. M. Whitesides, Angew. Chem. Int. Ed., 1998, 37, 2754.
2. R. Autar, A. S. Khan, M. Schad, J. Hacker, R. M. J. Liskamp and R. J. Pieters, ChemBioChem, 2003, 4, 1317;
3. J. A. F. Joosten, V. Loimaranta, C. C. M. Appeldoorn, S. Haataja, F. Ait El Maate, R. M. J. Liskamp, J. Finne and R. J. Pieters, J. Med. Chem., 2004, 47, 6499;
4. D. Arosio, I. Vrasidas, P. Valentini, R. M. J. Liskamp, R. J. Pieters and A. Bernardi, Org. Biomol. Chem., 2004, 2, 2113;
5. S. André, R. J. Pieters, I. Vrasidas, H. Kaltner, I. Kuwabara, F.-T. Liu, R. M. J. Liskamp and H.-J. Gabius, ChemBioChem, 2001, 2, 822;
6. J. A. F. Joosten, N. T. H. Tholen, F. Ait El Maate, A. J. Brouwer, G. W. van Esse, D. T. S. Rijkers, R. M. J. Liskamp and R. J. Pieters, Eur. J. Org Chem., 2005, 3182.
7. (a) G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendrimers and Dendrons: Concepts, Syntheses, Applications, Wiley, New York, 2001;
8. (b) J. M. J. Fréchet, Proc. Natl. Acad. Sci. USA, 2002, 99, 4782.
9. G. T. Hermanson, Bioconjugate Techniques, Academic Press Limited, London, UK, 1996;
10. A. Garman, Non-radioactive Labelling: A Practical Approach, Academic Press Limited, London, UK, 1997.
11. For recent examples of dendrimer modification using chemical ligation and/or sulfhydryl groups see: I. Van Baal, H. Malda, S. A. W. Reulen, T. M. Hackeng, M. Merkx and E. W. Meijer, Abstracts of Papers, 229th ACS National Meeting, San Diego, CA, United States, March 13-17, 2005 (2005);
12. A. Herrmann, G. Mihov, G. W. M. Vandermeulen, H.-A. Klok and K. Müllen, Tetrahedron, 2003, 59, 3925;
13. G. Mihov, D. Grebel-Koehler, A. Lübbert, G. W. M. VanderMeulen, A. Herrmann, H.-A. Klok and K. Müllen, Bioconjugate Chem., 2005, 16, 283;
14. I. Van Baal, H. Malda, S. A. Synowsky, J. L. T. van Dongen, T. M. Hackeng, M. Merkx and E. W. Meijer, Angew. Chem., Int. Ed., 2005, 44, 5052.
15. R. Huisgen, R. Knorr, L. Mobius and G. Szeimies, Chem. Ber., 1965, 98, 4014.
16. C. W. Tornøe, C. Christensen and M. Meldal, J. Org. Chem., 2002, 67, 3057.
17. V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596.
18. For recent reviews and applications see: R. Breinbauer and M. Köhn, ChemBioChem, 2003, 4, 1147;
19. Q. Wang, R. Chan, R. Hilgraf, V. V. Fokin, K. B. Sharpless and M. G. Finn, J. Am. Chem. Soc., 2003, 125, 3192.
20. S. J. E. Mulders, A. J. Brouwer, P. G. J. van der Meer and R. M. J. Liskamp, Tetrahedron Lett., 1997, 38, 631;
21. S. J. E. Mulders, A. J. Brouwer and R. M. J. Liskamp, Tetrahedron Lett., 1997, 38, 3085;
22. A. J. Brouwer, S. J. E. Mulders and R. M. J. Liskamp, Eur. J. Org. Chem., 2001, 1903;
23. A. J. Brouwer and R. M. J. Liskamp, Eur. J. Org. Chem., 2005, 487.
24. H. C. Kolb, M. G. Finn and K. B. Sharpless, Angew. Chem. Int. Ed., 2001, 40, 2004;
25. B. Helms, J. L. Mynar, C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 2004, 126, 15020;
26. P. Wu, A. K. Feldman, A. K. Nugent, C. J. Hawker, A. Scheel, B. Voit, J. Pyun, J. M. J. Frechet, K. B. Sharpless and V. V. Fokin, Angew. Chem. Int. Ed., 2004, 43, 2938.
27. K. A. Savin, M. Robertson, D. Gernert, S. Green, E. J. Hembre and J. Bishop, Mol. Diversity, 2003, 7, 171;
28. P. Appukkuttan, W. Dehaen, V. V. Fokin and E. Van der Eycken, Org. Lett., 2004, 6, 4223.
29. Azide 6 was prepared according to: S. G. Alvarez and M. T. Alvarez, Synthesis, 1997, 413.
30. Azides 7-10, 13 and 14 were synthesized according to: J. T. Lundquist, IV and J. C. Pelletier, Org. Lett., 2001, 3, 781.
31. azido peptides 11 and 12 were synthesized according to: D. T. S. Rijkers, H. H. R. van Vugt, H. J. F. Jacobs and R. M. J. Liskamp, Tetrahedron Lett., 2002, 43, 3657.
32. For a recent review concerning peptide-based dendrimers: L. Crespo, G. Sanclimens, M. Pons, E. Giralt, M, Royo and F. Albericio, Chem. Rev., 2005, 105, 1663. Peptide-based dendrimers are also reviewed in reference 3a.
33. Tesser's base is a mixture of dioxane, methanol and aq. NaOH, see: G. I. Tesser and I. C. Balvert-Geers, Int. J. Peptide Protein Res., 1975, 7, 295.
34. M. Zasloff, Proc. Natl. Acad. Sci. USA, 1987, 84, 5449.
35. R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk and H. Kessler, J. Am. Chem. Soc., 1996, 118, 7461.
36. R. Haubner, H.-J. Wester, F. Burkhart, R. Senekowitsch-Schmidtke, W. Weber, S. L. Goodman, H. Kessler and M. Schwaiger, J. Nucl. Med., 2001, 42, 326;
37. M. L. Janssen, W. J. Oyen, I. Dijkgraaf, L. F. Massuger, C. Frielink, D. S. Edwards, M. Rajopadhye, H. Boonstra, F. H. Corstens and O. C. Boerman, Cancer Res., 2002, 62, 6146;
38. G. Thurmshirn, U. Hersel, S. L. Goodman and H. Kessler, Chem. Eur. J., 2003, 9, 2717.