A copper-catalyzed, pH-neutral construction of high-enantiopurity peptidyl ketones from peptidic S-acylthiosalicylamides in air at room temperature

Angewandte Chemie - International Edition

Volumn 48, Issue 8, 2009, Pages 1417-1421

  Liebeskind, Lanny S ^a   Yang, Hao ^b   Li, Hao ^a  

^a EMORY UNIVERSITY   (United States)

^b ABBOTT LABORATORIES   (United States)

Author keywords

Copper; Cross coupling; Peptidomimetics; Protein modifications; Synthetic methods

Indexed keywords

ESTERIFICATION; ESTERS; FOURIER TRANSFORMS; KETONES; ORGANIC COMPOUNDS; SULFUR;

AEROBIC REACTIONS; BORONIC ACIDS; CROSS-COUPLING; ENANTIOPURITY; PEPTIDOMIMETICS; PROTEIN MODIFICATIONS; ROOM TEMPERATURES; SYNTHETIC METHODS; THIOL ESTERS;

COPPER;

AMIDE; COPPER; KETONE; PEPTIDE; SALICYLAMIDE DERIVATIVE;

AIR; ARTICLE; CATALYSIS; CHEMISTRY; PH; STEREOISOMERISM; SYNTHESIS; TEMPERATURE;

AIR; AMIDES; CATALYSIS; COPPER; HYDROGEN-ION CONCENTRATION; KETONES; PEPTIDES; SALICYLAMIDES; STEREOISOMERISM; TEMPERATURE;

EID: 60149110162     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804524     Document Type: Article

References (97)

1. L. X. Yin, J. Liebscher, Chem. Rev. 2007, 107, 133.
2. N. Miyaura in Topics in Current Chemistry, Springer, Heidelberg, 2006.
3. J. F. Hartwig, Synlett 2006, 1283.
4. J.-P. Corbet, G. Mignani, Chem. Rev. 2006, 106, 2651.
5. S. L. Buchwald, C. Mauger, G. Mignani, U. Scholzc, Adv. Synth. Catal. 2006, 348, 23.
6. K. H. Shaughnessy, R. B. DeVasher, Curr. Org. Chem. 2005, 9, 585.
7. R. Franzén, Y. Xu, Can. J. Chem. 2005, 83, 266.
8. I. P. Beletskaya, Pure Appl. Chem. 2005, 77, 2021.
9. B. Schlummer, U. Scholz, Adv. Synth. Catal. 2004, 346, 1599.
10. I. P. Beletskaya, A. V. Cheprakov, Coord. Chem. Rev. 2004, 248, 2337.
11. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558;
12. Angew. Chem. Int. Ed. 2003, 42, 5400.
13. R. G. Bergman, Nature 2007, 446, 391.
14. D. Alberico, M. E. Scott, M. Lautens, Chem. Rev. 2007, 107, 174.
15. D. R. Stuart, K. Fagnou, Science 2007, 316, 1172.
16. S. A. Reed, M. C. White, J. Am. Chem. Soc. 2008, 130, 3316.
17. M. S. Chen, M. C. White, Science 2007, 318, 783.
18. D. Kalyani, A. R. Dick, W. Q. Anani, M. S. Sanford, Tetrahedron 2006, 62, 11483.
19. L. J. Gooßen, N. Rodriguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824.
20. L. J. Gooßen, G. Deng, L. M. Levy, Science 2006, 313, 662.
21. F. Kakiuchi, N. Chatani, Adv. Synth. Catal. 2003, 345, 1077.
22. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2008, 130, 1128.
23. H.-Q. Do, O. Daugulis, J. Am. Chem. Soc. 2007, 129, 12404.
24. J. J. Mousseau, A. Larivée, A. B. Charette, Org. Lett. 2008, 10, 1641.
25. L.-C. Campeau, M. Bertrand-Laperle, J.-P. Leclerc, E. Ville-mure, S. Gorelsky, K. Fagnou, J. Am. Chem. Soc. 2008, 130, 3276.
26. R. A. Scheck, M. T. Dedeo, A. T. Iavarone, M. B. Francis, J. Am. Chem. Soc. 2008, 130, 11762.
27. K. M. Marks, G. P. Nolan, Nat. Methods 2006, 3, 591.
28. J. M. Antos, M. B. Francis, Curr. Opin. Chem. Biol. 2006, 10, 253.
29. S. Shaunak, A. Godwin, J.-W. Choi, S. Balan, E. Pedone, D. Vijayarangam, S. Heidelberger, I. Teo, M. Zloh, S. Brocchini, Nat. Chem. Biol. 2006, 2, 312.
30. S. Borman, Chem. Eng. News 2006, 84, 31.
31. A. Dantas de Araújo, J. M. Palomo, J. Cramer, O. Seitz, K. Alexandrov, H. Waldmann, Chem. Eur. J. 2006, 12, 6095.
32. C. Streu, E. Meggers, Angew. Chem. 2006, 118, 5773;
33. Angew. Chem. Int. Ed. 2006, 45, 5645.
34. N. S. Joshi, L. R. Whitaker, M. B. Francis, J. Am. Chem. Soc. 2004, 126, 15942.
35. J. P. Tam, J. Xu, K. D. Eom, Biopolymers 2001, 60, 194.
36. J. A. Prescher, C. R. Bertozzi, Nat. Chem. Biol. 2005, 1, 13.
37. B. N. Cook, C. R. Bertozzi, Bioorg. Med. Chem. 2002, 10, 829.
38. E. Saxon, C. R. Bertozzi, Annu. Rev. Cell Dev. Biol. 2001, 17, 1.
39. J. A. Prescher, D. H. Dube, C. R. Bertozzi, Nature 2004, 430, 873.
40. E. Saxon, C. R. Bertozzi, Science 2000, 287, 2007.
41. M. Whiting, J. Muldoon, Y.-C. Lin, S. M. Silverman, W. Lindstrom, A. J. Olson, H. C. Kolb, M. G. Finn, K. B. Sharpless, J. H. Elder, V. V. Fokin, Angew. Chem. 2006, 118, 1463;
42. Angew. Chem. Int. Ed. 2006, 45, 1435.
43. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem. 2001, 113, 2056;
44. Angew. Chem. Int. Ed. 2001, 40, 2004.
45. A. J. Link, D. A. Tirrell, J. Am. Chem. Soc. 2003, 125, 11164.
46. K. E. Beatty, F. Xie, Q. Wang, D. A. Tirrell, J. Am. Chem. Soc. 2005, 127, 14150.
47. The construction of enantiopure peptidyl ketones starting from naturally occurring amino acids is known. Although powerful, none of the known reactions take place under nonbasic (nonepimerizing) reaction conditions, nor are they general with respect to functional group compatibility, see: references [44-60].
48. T. Mittag, K. L. Christensen, K. B. Lindsay, N. C. Nielsen, T. Skrydstrup, J. Org. Chem. 2008, 73, 1088.
49. M. J. O'Donnell, M. D. Drew, R. S. Pottorf, W. L. Scott, J. Comb.Chem. 2000, 2, 172.
50. B. Munoz, C.-Z. Giam, C.-H. Wong, Bioorg. Med. Chem. 1994, 2, 1085.
51. T. Fukuyama, H. Tokuyama, Aldrichimica Acta 2004, 37, 87.
52. M. T. Reetz, Angew. Chem. 1991, 103, 1559;
53. Angew. Chem. Int. Ed. Engl. 1991, 30, 1531.
54. T. Ooi, M. Takeuchi, D. Kato, Y. Uematsu, E. Tayama, D. Sakai, K. Maruoka, J. Am. Chem. Soc. 2005, 127, 5073.
55. A. G. Myers, T. Yoon, Tetrahedron Lett. 1995, 36, 9429.
56. A. S. Florjancic, G. S. Sheppard, Synthesis 2003, 1653.
57. R. C. Klix, S. A. Chamberlin, A. V. Bhatia, D. A. Davis, T. K. Hayes, F. G. Rojas, R. W. Koops, Tetrahedron Lett. 1995, 36, 1791.
58. M. R. Paleo, F. J. Sardina, Tetrahedron Lett. 1996, 37, 3403.
59. J. Vazquez, F. Albericio, Tetrahedron Lett. 2002, 43, 7499.
60. A. R. Katritzky, K. N. B. Le, L. Khelashvili, P. P. Mohapatra, J. Org. Chem. 2006, 71, 9861.
61. K. Conrad, Y. Hsiao, R. Miller, Tetrahedron Lett. 2005, 46, 8587.
62. J. Liu, N. Ikemoto, D. Petrillo, J. D. Armstrong, Tetrahedron Lett. 2002, 43, 8223.
63. B. F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, A. Ricci, G. Varchi, Synlett 1998, 1013.
64. A. K. Sharma, P. J. Hergenrother, Org. Lett. 2003, 5, 2107.
65. Y. Zhang, T. Rovis, J. Am. Chem. Soc. 2004, 126, 15964.
66. A. Timmons, M. Seierstad, R. Apodaca, M. Epperson, D. Pippel, S. Brown, L. Chang, B. Scott, M. Webb, S. R. Chaplan, J. G. Breitenbucher, Bioorg. Med. Chem. Lett. 2008, 18, 2109.
67. B. E. Maryanoff, M. J. Costanzo, Bioorg. Med. Chem. 2008, 16, 1562.
68. M. J. Costanzo, H. R. Almond, Jr., L. R. Hecker, M. R. Schott, S. C. Yabut, H.-C. Zhang, P. Andrade-Gordon, T. W. Corcoran, E. C. Giardino, J. A. Kauffman, J. M. Lewis, L. de Garavilla, B. J. Haertlein, B. E. Maryanoff, J. Med. Chem. 2005, 48, 1984.
69. M. J. Costanzo, S. C. Yabut, H. R. Almond, Jr., P. Andrade-Gordon, T. W. Corcoran, L. de Garavilla, J. A. Kauffman, W. M. Abraham, R. Recacha, D. Chattopadhyay, B. E. Maryanoff, J. Med. Chem. 2003, 46, 3865.
70. J. C. Powers, J. L. Asgian, O. D. Ekici, K. E. James, Chem. Rev. 2002, 102, 4639.
71. D. L. Boger, H. Miyauchi, M. P. Hedrick, Bioorg. Med. Chem. Lett. 2001, 11, 1517.
72. R. Tripathy, M. A. Ator, J. P. Mallamo, Bioorg. Med. Chem. Lett. 2000, 10, 2315.
73. R. W. Marquis, Y. Ru, D. S. Yamashita, H.-J. Oh, J. Yen, S. K. Thompson, T. J. Carr, M. A. Levy, T. A. Tomaszek, C. F. Ijames, W. W. Smith, B. Zhao, C. A. Janson, S. S. Abdel-Meguid, K. J. DAlessio, M. S. McQueney, D. F. Veber, Bioorg. Med. Chem. 1999, 7, 581.
74. R. Calabretta, C. Giordano, C. Gallina, V. Morea, V. Consalvi, R. Scandurra, Eur. J. Med. Chem. 1995, 30, 931.
75. P. S. Dragovich, R. Zhou, S. E. Webber, T. J. Prins, A. K. Kwok, K. Okano, S. A. Fuhrman, L. S. Zalman, F. C. Maldonado, E. L. Brown, J. W. I. Meador, A. K. Patick, C. E. Ford, M. A. Brothers, S. L. Binford, D. A. Matthews, R. A. Ferre, S. T. Worland, Bioorg. Med. Chem. Lett. 2000, 10, 45.
76. M. Eda, A. Ashimori, F. Akahoshi, T. Yoshimura, Y. Inoue, C. Fukaya, M. Nakajima, H. Fukuyama, T. Imada, N. Nakamura, Bioorg. Med. Chem. Lett. 1998, 8, 919.
77. B. M. Wagner, R. A. Smith, P. J. Coles, L. J. Copp, M. J. Ernest, A. Krantz, J. Med. Chem. 1994, 37, 1833.
78. J. M. Villalobos, J. Srogl, L. S. Liebeskind, J. Am. Chem. Soc. 2007, 129, 15734.
79. I/ carboxylate cofactors ("first-generation" desulfitative coupling) provides improved functional group compatibility relative to organolithium, -magnesium, and -zinc reagents. The desulfi- tative coupling reaction occurs at neutral pH at or near ambient temperature and has proven valuable for the synthesis of peptidyl ketones. Two new pH-neutral first-generation protocols have been disclosed, the first is through boronic acids (a) H. Yang, H. Li, R. Wittenberg, M. Egi, W. Huang, L. S. Liebeskind, J. Am. Chem. Soc. 2007, 129, 1132;
80. b) H. Yang, L. S. Liebeskind, Org. Lett. 2007, 9, 2993) and a highly effective and general variant of that chemistry in which organostannanes rather than boronic acids are the reaction partners (c) H. Li, H. Yang, L. S. Liebeskind, Org. Lett. 2008, 10, 4375).
81. Simple HPLC analysis was used for the control experiments probing the influence of additives. For the added amines, benzoic acid, and glucose, the HPLC traces only showed the peaks corresponding to the formation of products and full disappearance of the peaks corresponding to the thiol ester starting material.
82. C. M. Gross, D. Lelievre, C. K. Woodward, G. Barany, J. Pept. Res. 2005, 65, 395.
83. J. Alsina, S. A. Kates, G. Barany, F. Albericio, Methods Mol. Biol. 2005, 298, 195.
84. J. Alsina, F. Albericio, Biopolymers 2003, 71, 454.
85. J. A. Camarero, A. Adeva, T. W. Muir, Lett. Pept. Sci. 2000, 7, 17.
86. A. Sewing, D. Hilvert, Angew. Chem. 2001, 113, 3503;
87. Angew. Chem. Int. Ed. 2001, 40, 3395.
88. J. Offer, C. N. C. Boddy, P. E. Dawson, J. Am. Chem. Soc. 2002, 124, 4642.
89. S. Aimoto, Biopolymers 1999, 51, 247.
90. J. P. Gogarten, A. G. Senejani, O. Zhaxybayeva, L. Olendzenski, E. Hilario, Annu. Rev. Microbiol. 2002, 56, 263.
91. X.-Q. Liu, Annu. Rev. Genet. 2000, 34, 61.
92. J. A. Camarero, Protein Pept. Lett. 2005, 12, 721.
93. C. J. Noren, J. M. Wang, F. B. Perler, Angew. Chem. 2000, 112, 458;
94. Angew. Chem. Int. Ed. 2000, 39, 450.
95. R. David, M. P. O. Richter, A. G. Beck-Sickinger, Eur. J. Biochem. 2004, 271, 663.
96. T. W. Muir, Annu. Rev. Biochem. 2003, 72, 249.
97. K. Severinov, T. W. Muir, J. Biol. Chem. 1998, 273, 16205.