Synthesis of a biologically active triazole-containing analogue of cystatin A through successive peptidomimetic alkyne-azide ligations

Angewandte Chemie - International Edition

Volumn 51, Issue 3, 2012, Pages 718-722

  Valverde, Ibai E ^a   Lecaille, Fabien ^b   Lalmanach, Gilles ^b   Aucagne, Vincent ^a   Delmas, Agnès F ^a  

^a CENTRE DE BIOPHYSIQUE MOLÉCULAIRE   (France)

^b UNIVERSITÉ DE TOURS   (France)

Author keywords

click chemistry; peptidomimetics; proteases; proteins; synthetic methods

Indexed keywords

AMINO ACID PROTEINS; BIOACTIVE PROTEINS; CHEMICAL PRODUCTION; CLICK CHEMISTRY; CYSTATINS; PEPTIDE FRAGMENTS; PEPTIDOMIMETICS; PROTEASES; SYNTHETIC METHODS; TERMINAL ALKYNE;

ACETYLENE; AMINO ACIDS; NITROGEN COMPOUNDS; PROTEINS; SURGICAL EQUIPMENT;

BIOSYNTHESIS;

ALKYNE; AZIDE; CATHEPSIN; PEPTIDOMIMETIC AGENT; STEFIN A; TRIAZOLE DERIVATIVE;

AMINO ACID SEQUENCE; ARTICLE; CANCER INVASION; CHEMISTRY; CLICK CHEMISTRY; CYCLIZATION; DRUG ANTAGONISM; HUMAN; METHODOLOGY; MOLECULAR GENETICS; SYNTHESIS; TUMOR CELL LINE;

ALKYNES; AMINO ACID SEQUENCE; AZIDES; CATHEPSINS; CELL LINE, TUMOR; CLICK CHEMISTRY; CYCLIZATION; CYSTATIN A; HUMANS; MOLECULAR SEQUENCE DATA; NEOPLASM INVASIVENESS; PEPTIDOMIMETICS; TRIAZOLES;

EID: 84855756802     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107222     Document Type: Article

References (49)

1. C. C. Liu, P. G. Schultz, Annu. Rev. Biochem. 2010, 79, 413-444.
2. M. Schnölzer, S. B. Kent, Science 1992, 256, 221-225
3. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science 1994, 266, 776-779.
4. For an example of introduction of a depsipeptidic bond:, D. W. Low, M. G. Hill, J. Am. Chem. Soc. 2000, 122, 11039-11040
5. for an example of introduction of a cis-peptide bond mimic:, A. Tam, U. Arnold, M. B. Soellner, R. T. Raines, J. Am. Chem. Soc. 2007, 129, 12670-12671.
6. M. Baca, S. B. Kent, Proc. Natl. Acad. Sci. USA 1993, 90, 11638-11642
7. H. F. Gaertner, R. E. Offord, R. Cotton, D. Timms, R. Camble, K. Rose, J. Biol. Chem. 1994, 269, 7224-7230
8. D. R. Englebretsen, B. Garnham, P. F. Alewood, J. Org. Chem. 2002, 67, 5883-5890.
9. N. Assem, A. Natarajan, A. K. Yudin, J. Am. Chem. Soc. 2010, 132, 10986-10987.
10. C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002, 67, 3057-3064
11. V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless, Angew. Chem. 2002, 114, 2708-2711
12. Angew. Chem. Int. Ed. 2002, 41, 2596-2599.
13. A. Brik, J. Alexandratos, Y. Lin, J. H. Elder, A. J. Olson, A. Wlodawer, D. S. Goodsell, C.-H. Wong, ChemBioChem 2005, 6, 1167-1169
14. Y. Hua, A. H. Flood, Chem. Soc. Rev. 2010, 39, 1262-1271
15. W. S. Horne, M. K. Yadav, C. D. Stout, M. R. Ghadiri, J. Am. Chem. Soc. 2004, 126, 15366-15367.
16. E. Ko, J. Liu, L. M. Perez, G. Lu, A. Schaefer, K. Burgess, J. Am. Chem. Soc. 2011, 133, 462-477.
17. J. T. Lundquist IV, J. C. Pelletier, Org. Lett. 2001, 3, 781-783.
18. For a recent review about the use of triazoles in peptidomimetics, see:, D. J. Pedersen, A. Abell, Eur. J. Org. Chem. 2011, 2399-2411.
19. W. S. Horne, C. A. Olsen, J. M. Beierle, A. Montero, M. R. Ghadiri, Angew. Chem. 2009, 121, 4812-4818
20. Angew. Chem. Int. Ed. 2009, 48, 4718-4724
21. J. M. Beierle, W. S. Horne, J. H. van Maarseveen, B. Waser, J. C. Reubi, M. R. Ghadiri, Angew. Chem. 2009, 121, 4819-4823
22. Angew. Chem. Int. Ed. 2009, 48, 4725-4729
23. V. D. Bock, D. Speijer, H. Hiemstra, J. H. van Maarseveen, Org. Biomol. Chem. 2007, 5, 971-975.
24. V. Aucagne, D. A. Leigh, Org. Lett. 2006, 8, 4505-4507
25. O. D. Montagnat, G. Lessene, A. B. Hughes, Tetrahedron Lett. 2006, 47, 6971-6974.
26. I. E. Valverde, A. F. Delmas, V. Aucagne, Tetrahedron 2009, 65, 7597-7602
27. P. M. Gramlich, S. Warncke, J. Gierlich, T. Carell, Angew. Chem. 2008, 120, 3491-3493
28. Angew. Chem. Int. Ed. 2008, 47, 3442-3444
29. B. C. Doak, M. J. Scanlon, J. S. Simpson, Org. Lett. 2011, 13, 537-539.
30. F. Lecaille, J. Kaleta, D. Brömme, Chem. Rev. 2002, 102, 4459-4488.
31. O. Vasiljeva, T. Reinheckel, C. Peters, D. Turk, V. Turk, B. Turk, Curr. Pharm. Des. 2007, 13, 387-403
32. J. Reiser, B. Adair, T. Reinheckel, J. Clin. Invest. 2010, 120, 3421-3431.
33. C. Palermo, J. A. Joyce, Trends Pharmacol. Sci. 2008, 29, 22-28
34. M. Kasabova, A. Saidi, C. Naudin, J. Sage, F. Lecaille, G. Lalmanach, Clin. Rev. Bone Miner. Metab. 2011, 9, 148-161
35. B. Turk, Nat. Rev. Drug Discovery 2006, 5, 785-799.
36. S. Jenko, I. Dolenc, G. Guncar, A. Dobersek, M. Podobnik, D. Turk, J. Mol. Biol. 2003, 326, 875-885.
37. W. Bode, R. Huber, Biochim. Biophys. Acta Protein Struct. Mol. Enzymol. 2000, 1477, 241-252.
38. J. Alsina, T. S. Yokum, F. Albericio, G. Barany, J. Org. Chem. 1999, 64, 8761-8769.
39. D. Bonnet, S. Riché, S. Loison, R. Dagher, M. C. Frantz, L. Boudier, R. Rahmeh, B. Mouillac, J. Haiech, M. Hibert, Chem. Eur. J. 2008, 14, 6247-6254
40. 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. S. Estrada, A. Pavlova, I. Björk, Biochemistry 1999, 38, 7339-7345.
42. T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun, M. Mutter, J. Am. Chem. Soc. 1996, 118, 9218-9227.
43. G.-A. Cremer, H. Tariq, A. F. Delmas, J. Pept. Sci. 2006, 12, 437-442
44. F. García-Martín, P. White, R. Steinauer, S. Côté, J. Tulla-Puche, F. Albericio, Biopolymers 2006, 84, 566-575.
45. E. Pol, S. L. Olsson, S. Estrada, T. W. Prasthofer, I. Björk, Biochem. J. 1995, 311, 275-282.
46. E. A. Auerswald, D. K. Nägler, A. J. Schulze, R. A. Engh, G. Genenger, W. Machleidt, H. Fritz, Eur. J. Biochem. 1994, 224, 407-415.
47. G. D. Green, A. A. Kembhavi, M. E. Davies, A. J. Barrett, Biochem. J. 1984, 218, 939-946.
48. B. Japelj, J. P. Waltho, R. Jerala, Proteins Struct. Funct. Genet. 2004, 54, 500-512.
49. L. Gillet, S. Roger, P. Besson, F. Lecaille, J. Gore, P. Bougnoux, G. Lalmanach, J. Y. Le Guennec, J. Biol. Chem. 2009, 284, 8680-8691.