Cydative cleavage through dipolar cycloaddition: Polymer-bound azidopeptidylphosphoranes deliver locked cis-triazolylcyclopeptides as privileged protein binders

Angewandte Chemie - International Edition

Volumn 49, Issue 31, 2010, Pages 5378-5382

  Ahsanullah, ^c   Rademann, Jörg ^a,b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b LEIBNIZ INSTITUT FÜR MOLEKULARE PHARMAKOLOGIE   (Germany)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

1,3 dipolar cycloaddition; Biocompatible ligation; Cyclopeptides; Peptidomimetics; Triazoles

Indexed keywords

CHEMICAL EQUATIONS; CYCLIZED PRODUCTS; CYCLOPEPTIDES; DIPOLAR CYCLOADDITIONS; PEPTIDOMIMETICS; PHOSPHORANES; PROTEIN BINDERS; SOLID SUPPORTS; TRIAZOLE RING;

OLIGOMERIZATION;

CYCLOADDITION;

AZIDE; CYCLOPEPTIDE; PHOSPHINE; PHOSPHINE DERIVATIVE; POLYMER;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; PROTEIN BINDING;

AZIDES; CYCLIZATION; MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; PHOSPHINES; POLYMERS; PROTEIN BINDING;

EID: 77954850250     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200904980     Document Type: Article

References (56)

1. a) H. Kessler, Angew. Chem. 1982, 94, 509-520
2. Angew. Chem. Int. Ed. Engl. 1982, 21, 512-523
3. b) R. M. Wenger, Angew. Chem. 1985, 97, 88-96
4. Angew. Chem. Int. Ed. Engl 1985, 24, 77-85
5. c) K. Maria, T. Theodore, D. Spyros, D. George, M. Minos-Timotheos, L. Eliada, M. John, A. Vasso, Curr. Med. Chem, 2006, 13, 2221-2232
6. d) Y. Hamada, T. Shioiri, Chem. Rev. 2005, 105, 4441-4482.
7. a) S. W. Millward, S. Fiacco, R. J. Austin, R. W. Roberts, ACS Chem. Biol. 2007, 2, 625-634
8. b) A. Tavassoli, Q. Lu, J. Gam, H. Pan, S. J. Benkovic, S. N. Cohen, ACS Chem. Biol. 2008, 3, 757-764
9. c) S. Bonetto, L. Spadola, A. G. Buchanan, L. Jermutus, J. Lund, FASEB J. 2009, 23, 575-585
10. http://www.nlm.nih.gov/cgi/mesh./2009/MB-cgi?mode = &term = Cyclic + Peptides#TreeD12.644.641.
11. a) R. Haubner, R. Gratias, B. Diefenbach, S. L. Goodman, A. Jonczyk, H. Kessler, J. Am. Chem. Soc. 1996, 118, 7461-7472
12. b) A. Montero, J. M. Beierle, C. A. Olsen, M. R. Ghadiri, J. Am. Chem. Soc. 2009, 131, 3033-3041
13. a) W. S. Home, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009, 121, 4812-4818
14. Angew. Chem. Int. Ed. 2009, 48, 4718-4724
15. b) J. M. Beierle, W. S. Home, J. H. van Maarseveen, B. Waser, J. C. Reubi, M. R. Ghadiri, Angew. Chem. 2009, 121, 4819-4823
16. Angew. Chem, Int. Ed. 2009, 48, 4725-4729.
17. a) P. Wipf, Chem. Rev. 1995, 95, 2115-2134
18. b) J. S. Davies, J. Pept. Sci. 2003, 9, 471-501
19. c) U. Schmidt, U. Beutler, A. Lieberknecht, Angew. Chem. 1989, 101, 344-346
20. Angew. Chem. Int. Ed. Engl. 1989, 28, 333-334
21. a) M. C. Alcaro, G. Sabatino, J. Uziel, M. Chelli, M. Ginanneschi, P. Rovero, A. M. Papini, J. Pept. Sci. 2004, 10, 218-228;
22. b) M. Gonçalves, K. Estieu-Gionnet, G. Lata, M. Bayle, N. Betz, G. Déléris, Tetrahedron 2005, 61, 7789-7795
23. c) J. Tulla-Puche, G. Barany, J. Org. Chem. 2004, 69, 4101-4107.
24. a) S. Punna, J. Kuzelka, Q. Wang, M. G. Finn, Angew. Chem. 2005, 117, 2255-2260
25. Angew. Chem. Int. Ed. 2005, 44, 2215-2220
26. b) R. Jagasia, J. M. Holub, M. Bollinger, K. Kirshenbaum, M. G. Finn, J. Org. Chem. 2009, 74, 2964-2974
27. c) R. A. Turner, A. G. Oliver, R. S. Lokey, Org. Lett. 2007, 9, 5011-5014
28. d) J. M. Holub, H. Jang, K. Kirshenbaum, Org. Lett. 2007, 9, 3275-3278.
29. For reviews on cyclative cleavage reactions see: a) P. Blaney, R. Grigg, V. Sridharan, Chem. Rev. 2002, 102, 2607-2624
30. b) M. Jung, M. Wiehn, S. Bräse, Top. Curr. Chem. 2007, 278, 1-88
31. c) J. H. van Maarseveen, Comb. Chem. High Throughput Screening 1998, 1, 185-214
32. d) A. Ganesan in Methods in Enzymology: Combinatorial Chemistry, Vol.369 (Eds.: G. Morales, B. A. Bunin), Academic Press, San Diego, 2003, pp. 415-434
33. e) R. Shi, F. Wang, B. Yan, Int. J. Pept. Res. Ther. 2007, 73, 213-219.
34. a) C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064
35. b) V. V. Rostovtsev, L. G. Green, V. V. Fokin, K.B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
36. Angew. Chem. Int. Ed. 2002, 41, 2596-2599
37. c) L. Zhang, J. Chen, P. Xue, H. H. Y. Sun, I. D. Williams, K. B. Sharpless, V V. Fokin, G. Jia, J. Am. Chem. Soc. 2005, 127, 15998-15999.
38. Y. Liu, L. Zhang, J. Wan, Y. Li, Y. Xu, Y. Pan, Tetrahedron 2008, 64, 10728-10734.
39. a) S. Cantel, A. Le Chevalier-Isaad, M. Scrima, J. J. Levy, R. D. DiMarchi, P. Rovero, J. A. Halperin, A. M. D'Ursi, A. M. Papini, M. Chorev, J. Org. Chem. 2008, 73, 5663-5674
40. b) J. Springer, K. R. de Cuba, S. Calvet-Vitale, J. A. J. Geenevasen, P. H. H. Hermkens, H. Hiemstra, J. H. van Maarseveen, Eur. J. Org. Chem. 2008, 2592-2600
41. c) V. Goncalves, B. Gautier, A. Regazzetti, P. Coric, S. Bouaziz, C. Garbay, M. Vidal, N. Inguimbert, Bioorg. Med. Chem. LetL 2007, 17, 5590-5594.
42. a) Y. Angell, K. Burgess, J. Org. Chem. 2005, 70, 9595-9598;
43. b) V. D. Bock, R. Perciaccante, T. P. Jansen, H. Hiemstra, J. H. van Maarseveen, Org. Lett. 2006, 8, 919-922
44. c) V. D. Bock, D. Speijer, H. Hiemstra, J. H. van Maarseveen, Org. Biomol. Chem. 2007, 5, 971-975.
45. a) W. S. Home, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2003, 125, 9372-9376
46. b) J. H. van Marseveen, W. S. Home, M. R. Ghadiri, Org. Lett. 2005, 7, 4503-4506.
47. Ahsanullah, P. Schmieder, R. Kühne, J. Rademann, Angew. Chem. 2009, 121, 5143-5147
48. a) S. Weik, J. Rademann, Angew. Chem. 2003, 115, 2595-2598
49. Angew. Chem. Int. Ed. 2003, 42, 2491-2494
50. b) A. El-Dahshan, S. Weik, J. Rademann, Org. Lett. 2007, 9, 949-952
51. J.T. Lundquist IV, J.C. Pelletier, Org. Lett. 2001, 3, 781-783
52. a) G. O. Jones, K. N. Houk, J. Org. Chem. 2008, 73, 1333-1342
53. b) C. Di Valentin, M. Freccero, R. Gandolfi, A. Rastelli, J. Org. Chem. 2000, 65, 6112-6120
54. c) L.R. Domingo, M. T Picher, Tetrahedron 2004, 60, 5053-5058
55. d) L. R. Domingo, M. T. Picher, P. Arroyo, J. A. Sàez, J. Org. Chem. 2006, 71, 9319-9330
56. II catalysis were discussed in a recent PhD thesis: J. Springer, University of Amsterdam, 2008, chap. 4, pp. 106-126, ( http://dare.uva.nl/ document/116338). To compare the efficiency of our new approach for the synthesis of cis-triazolyl cyclopeptides with, the existing methods, compound 14 was prepared analogously to one example reported in reference [5a]. The yield of the cyclative cleavage was 64 %, while the yield of the lactamization procedure was 9 %.