Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A

Journal of Organic Chemistry

Volumn 68, Issue 25, 2003, Pages 9835-9838

  Berthelot, Alexandra ^a   Piguel, Sandrine ^a   Le Dour, Gwennaël ^a   Vidal, Joëlle ^a  

^a UNIVERSITÉ DE RENNES 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC SIDE CHAINS;

ESTERS; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

7 BROMOTRYPTOPHAN METHYL ESTER; BENZOPHENONE DERIVATIVE; GLYCINE BENZOPHENONE IMINE; MACROCYCLIC COMPOUND; NICKEL; PROTEASOME INHIBITOR; TMC 95A; TMC 95B; TMC 95C; TMC 95D; TRIPEPTIDE; TRYPTOPHAN DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; ENANTIOSELECTIVITY; PEPTIDE SYNTHESIS;

ALKYLATION; BROMINE; HYDROCARBONS, AROMATIC; HYDROCARBONS, HALOGENATED; IMINES; OLIGOPEPTIDES; PEPTIDES, CYCLIC; PROTEASE INHIBITORS; STEREOISOMERISM; TRYPTOPHAN;

EID: 0344235341     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035256c     Document Type: Article

References (50)

1. (a) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105-109.
2. (b) Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995.
3. Kobayashi, H.; Shin-Ya, K.; Furihata, K.; Najai, K.; Suzuki, K. I.; Hayakawa, Y.; Seto, H.; Yun, B. S.; Ryoo, I. J.; Kim, J. S.; Kim, C. J.; Yoo, I. D. J. Antibiot. 2001, 54, 1019-1024.
4. Singh, S. B.; Jayasuriya, H.; Salituro, G. M.; Zink, D. L.; Shafiee, A.; Heimbuch, B.; Silverman, K. C.; Lingham, R. B.; Genilloud, O.; Teran, A.; Vilella, D.; Felock, P.; Hazuda D. J. Nat. Prod. 2001, 64, 874-882.
5. Matsuzaki, K.; Ikeda, H.; Ogino, T.; Matsumoto, A.; Woodruff, H. B.; Tanaka, H.; Omura, S. J. Antibiot. 1994, 47, 1173-1174.
6. (a) Naruse, N.; Tenmyo, O.; Kobaru, S., Hatori, M.; Tomika, K.; Hamagishi, Y.; Oki, T. J. Antibiot. 1993, 46, 1804-1811.
7. (b) Naruse, N.; Oka, M.; Konishi, M.; Oki, T. J. Antibiot. 1993, 46, 1812-1818.
8. Seto, H.; Fujioka, T.; Furihata, K.; Kaneko, I.; Takahashi, S. Tetrahedron Lett. 1989, 30, 4987-4990.
9. Hedge, V. R.; Puar, M. S.; Patel, M.; Gullo, V. P.; Pramanick, B.; Jenh C. H. Tetrahedron Lett. 2002, 43, 5339-5341.
10. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303-2304.
11. For reviews on proteasome inhibitors, see: Kisselev, A. F.; Goldberg, A. L. Chem. Biol. 2001, 8, 739-758;
12. Myung, J.; Kim, K. B.; Crews, C. M. Med. Res. Rev. 2001, 21, 245-273.
13. For review on proteasome, see: Groll, M.; Huber, R. Int. J. Biochem. Cell Biol. 2003, 35, 606-616 and references therein.
14. Adams, J. Drug Discovery Today 2003, 8, 307-315.
15. Recently, proteasome inhibitor VELCADE (PS-341 or bortezomib) received FDA approval in the treatment of multiple myeloma, a type of blood cancer. See http://millennium.com/.
16. (a) Ma, D.; Wu, Q. Tetrahedron Lett. 2000, 41, 9089-9093.
17. (b) Albrecht, B. K.; Williams, R. M. Tetrahedron Lett. 2001, 42, 2755-2757.
18. (c) Ma, D.; Wu, Q. Tetrahedron Lett. 2001, 42, 5279-5281.
19. (d) Inoue, M.; Furuyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
20. (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970.
21. (b) Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
22. Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515.
23. During the preparation of our manuscript, a second total synthesis of TMC-95A was published. Inoue, M.; Sakazaki, H.; Furuyama, H.; Hirama, M. Angew. Chem., Int. Ed. 2003, 42, 2654-2657.
24. Kaiser, M.; Groll, M.; Renner, C.; Huber, R.; Moroder, L. Angew. Chem., Int. Ed. 2002, 41, 780-783.
25. Groll, M.; Koguchi, Y.; Huber, R.; Kohno, J. J. Mol. Biol. 2001, 311, 543-548.
26. (a) Bartoli, G.; Palmieri, G. Tetrahedron Lett. 1989, 30, 2129-2132.
27. (b) Bartoli, G.; Bosco, M.; Dalpozzo, R.; Palmieri, G.; Marcantoni, E. J. Chem. Soc., Perkin Trans. 1 1991, 2757-2761.
28. Sundberg R. J. Best Synthetic Methods: Indoles Academic Press: New York, 1996.
29. (b) Ohta, T.; Yamato, Y.; Tahira, H.; Somei, M. Heterocycles 1987, 26, 2817-2822.
30. (a) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415.
31. (b) O'Donnell, M. J. Aldrichim. Acta 2001, 34, 3-15.
32. Enantiopurity was determined by HPLC; see the Supporting Information.
33. (a) Allen, M. C.; Brundish, D. E.; Wade, R. J. Chem. Soc., Perkin Trans. 1 1980, 1928-1932.
34. (b) Konda-Yamada, Y.; Okada, C.; Yoshida, K.; Umeda, Y.; Arima, S.; Sato, N.; Kai, T.; Takayanagi, H.; Harigaya, Y. Tetrahedron 2002, 58, 7851-7861.
35. Bodansky, M.; Bodansky, A. The practice of peptide synthesis, 2nd rev. ed.; Springer-Verlag: Berlin, New York, 1994.
36. Williams, E. B.; Krishnaswamy, S.; Mann, K. G. J. Biol. Chem. 1989, 264, 7536-7545.
37. (a) Sy W.-W. Tetrahedron Lett. 1993, 34, 6223-6224.
38. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
39. (a) Giroux, A.; Han, Y.; Prasit, P. Tetrahedron Lett. 1997, 38, 3841-3844.
40. (b) Baudoin, O.; Guénard D.; Guéritte, F. J. Org. Chem. 2000, 65, 9268-9271.
41. (c) Carbonnelle, A.-C.; Zhu, J. Org. Lett. 2000, 2, 3477-3480.
42. Elder, A. M.; Rich, D. H. Org. Lett. 1999, 1, 1443-1446.
43. (a) Semmelhack, M. F.; Helquist, P.; Jones, L. D.; Keller, L.; Menelson, L.; Speltz Ryono, L.; Gorzynski Smith, J.; Stauffer, R. D. J. Am. Chem. Soc. 1981, 103, 6460-6471.
44. (b) Kende, A. S.; Liebeskind L. S.; Braitsch, D. M. Tetrahedron Lett. 1975, 39, 3375-3378.
45. + 708.3009, found 708.3008) compounds.
46. Carruthers, W.; Coggins, P.; Weston, J. B. J. Chem. Soc., Perkin Trans. 1 1991, 611-616.
47. 2 carbon at the C-6 position in TMC-95 precursor or analogue prevented macrolactamization from occurring. See ref 14a and: Kaiser, M.; Milbradt, A. G.; Moroder, L. Lett. Pept. Sci. 2002, 9, 65-70.
48. See, for instance: (a) Beugelmans, R.; Roussi, G.; González Gonzdlez Zamora, E.; Carbonnelle, A.-C. Tetrahedron 1999, 55, 5089-5112.
49. (b) Roussi, G.; González Zamora, E.; Carbonnelle, A.-C.; Beugelmans, R. Heterocycles 1999, 51, 2041-2063.
50. (c) Bagley, M. C.; Hind, S. L.; Moody, C. J. Tetrahedron Lett. 2000, 41, 6897-6900.