In situ thioester formation for protein ligation using α-methylcysteine

Chemical Science

Volumn 5, Issue 2, 2013, Pages 766-770

  Burlina, Fabienne ^a,b,c   Papageorgiou, George ^d   Morris, Caroline ^d   White, Peter D ^e   Offer, John ^d  

^a SORBONNE UNIVERSITÉ   (France)

^b CNRS   (France)

^c Centre National de la Recherche Scientifique   (France)

^d Natl Insitiute for Medical Research   (United Kingdom)

^e Merck Chemicals   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

C-TERMINUS; CHEMICAL PROTEIN SYNTHESIS; FULLY COMPATIBLE; MODEL PROTEINS; PEPTIDE LIGATIONS; PEPTIDE SYNTHESIS; PEPTIDE THIOESTERS; PROTEIN LIGATION;

AMINO ACIDS; BIOSYNTHESIS;

PEPTIDES;

EID: 84891388712     PISSN: 20416520     EISSN: 20416539     Source Type: Journal    
DOI: 10.1039/c3sc52140k     Document Type: Article

References (59)

1. D. Kahne, W. C. Still, J. Am. Chem. Soc, 1988, 110, 7529-7534
2. R. A. R. Bryant, D. E. Hansen, J. Am. Chem. Soc, 1996, 118, 5498-5499
3. J. L. Radkiewicz, H. Zipse, S. Clarke, K. N. Houk, J. Am. Chem. Soc, 2001, 123, 3499-3506
4. J. W. Suggs, R. M. Pires, Tetrahedron Lett, 1997, 38, 2227-2230
5. N. M. Fernandes, F. Fache, M. Rosen, P.-L. Nguyen, D. E. Hansen, J. Org. Chem, 2008, 73, 6413-6416
6. K. Tani, B. M. Stoltz, Nature, 2006, 441, 731-734
7. A. J. Kirby, I. V. Komarov, P. D. Wothers, N. Feeder, Angew. Chem, Int. Ed, 1998, 37, 785-786
8. J. Clayden, Y. J. Y. Foricher, H. K. Lam, Eur. J. Org. Chem, 2002, 3558-3565
9. M. Hutchby, C. E. Houlden, M. F. Haddow, S. N. Tyler, G. C. Lloyd-Jones, K. I. Booker-Milburn, Angew. Chem, Int. Ed, 2012, 51, 548-551
10. J. Clayden, Nature, 2012, 481, 274-275
11. A. Romanelli, A. Shekhtman, D. Cowburn, T. W. Muir, Proc. Natl. Acad. Sci. U. S. A, 2004, 101, 6397-6402
12. A. Fersht, J. Am. Chem. Soc, 1971, 93, 3504-3514
13. S. B. Kent, Chem. Soc. Rev, 2009, 38, 338-351
14. T. M. Hackeng, J. H. Griffin, P. E. Dawson, Proc. Natl. Acad. Sci. U. S. A, 1999, 96, 10068-10073
15. Y. Makimura, T. Kiuchi, M. Izumi, S. Dedola, Y. Ito, Y. Kajihara, Carbohydr. Res, 2012, 364, 41-48
16. Z. P. Gates, J. R. Stephan, D. J. Lee, S. B. Kent, Chem. Commun, 2013, 49, 786-788
17. F. Mende, O. Seitz, Angew. Chem, Int. Ed, 2011, 50, 1232-1240
18. D. Macmillan, A. Adams, B. Premdjee, Isr. J. Chem, 2011, 51, 885-899
19. R. Ingenito, E. Bianchi, D. Fattori, A. Pessi, J. Am. Chem. Soc, 1999, 121, 11369-11374
20. R. R. Flavell, M. Huse, M. Goger, M. Trester-Zedlitz, J. Kuriyan, T. W. Muir, Org. Lett, 2002, 4, 165-168
21. Y. Shin, K. A. Winans, B. J. Backes, S. B. H. Kent, J. A. Ellman, C. R. Bertozzi, J. Am. Chem. Soc, 1999, 121, 11684-11689
22. F. Burlina, C. Morris, R. Behrendt, P. White, J. Offer, Chem. Commun, 2012, 48, 2579-2581
23. J. B. Blanco-Canosa, P. E. Dawson, Angew. Chem, Int. Ed, 2008, 47, 6851-6855
24. G. M. Fang, J. X. Wang, L. Liu, Angew. Chem, Int. Ed, 2012, 51, 10347-10350
25. J. Kang, D. Macmillan, Org. Biomol. Chem, 2010, 8, 1993-2002
26. H. Hojo, Y. Onuma, Y. Akimoto, Y. Nakahara, Y. Nakahara, Tetrahedron Lett, 2007, 48, 25-28
27. H. Hojo, Y. Murasawa, H. Kartayama, T. Ohira, Y. Nakahara, Y. Nakahara, Org. Biomol. Chem, 2008, 6, 1808-1813
28. P. Botti, M. Villain, S. Manganiello, H. Gaertner, Org. Lett, 2004, 6, 4861-4864
29. N. Ollivier, J. Dheur, R. Mhidia, A. Blanpain, O. Melnyk, Org. Lett, 2010, 12, 5238-5241
30. N. Ollivier, J. Vicogne, A. Vallin, H. Drobecq, R. Desmet, O. El Mahdi, B. Leclercq, G. Goormachtigh, V. Fafeur, O. Melnyk, Angew. Chem, Int. Ed, 2011, 51, 209-213
31. W. Hou, X. Zhang, F. Li, C.-F. Liu, Org. Lett, 2011, 13, 386-389
32. K. Sato, A. Shigenaga, K. Tsuji, S. Tsuda, Y. Sumikawa, K. Sakamoto, A. Otaka, ChemBioChem, 2011, 12, 1840-1844
33. J. Kang, J. P. Richardson, D. Macmillan, Chem. Commun, 2009, 407-409
34. J. Masania, J. Li, S. J. Smerdon, D. Macmillan, Org. Biomol. Chem, 2010, 8, 5113-5119
35. B. Cowper, D. J. Craik, D. Macmillan, ChemBioChem, 2013, 14, 809-812
36. D. Macmillan, M. De Cecco, N. L. Reynolds, L. F. Santos, P. E. Barran, J. R. Dorin, ChemBioChem, 2011, 12, 2133-2136
37. A. J. Kirby, Adv. Phys. Org. Chem, 1980, 17, 183-278
38. J. R. Reasenberg, S. D. Goldberg, J. Am. Chem. Soc, 1945, 67, 933
39. N. Metanis, E. Keinan, P. E. Dawson, Angew. Chem, Int. Ed, 2010, 49, 7049-7053
40. H. Rohde, J. Schmalisch, Z. Harpaz, F. Diezmann, O. Seitz, ChemBioChem, 2011, 12, 1396-1400
41. J. Lukszo, D. Patterson, F. Albericio, S. A. Kates, Lett. Pept. Sci, 1996, 3, 157-166
42. Y. Fu, L. G. J. Hammarström, T. J. Miller, F. R. Fronczek, M. L. McLaughlin, R. P. Hammer, J. Org. Chem, 2001, 66, 7118-7124
43. R. J. Topping, I. Nuiry, J. Mastriona, J. A. Moss, Tetrahedron Lett, 2008, 49, 2907-2910
44. W. Lu, M. A. Starovasnik, S. B. Kent, FEBS Lett, 1998, 429, 31-35
45. N. Fotouhi, N. G. Galakatos, D. S. Kemp, J. Org. Chem, 1989, 54, 2803-2817
46. C. M. Gross, D. Lelievre, C. K. Woodward, G. Barany, J. Pept. Res, 2005, 65, 395-410
47. N. Metanis, D. Hilvert, Angew. Chem, Int. Ed, 2012, 51, 5585-5588
48. M. Quibell, W. G. Turnell, T. Johnson, J. Org. Chem, 1994, 59, 1745-1750
49. E. C. Johnson, S. B. Kent, J. Am. Chem. Soc, 2006, 128, 7140-7141
50. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. Kent, Science, 1994, 266, 776-779
51. P. E. Dawson, M. Churchill, M. R. Ghadiri, S. B. H. Kent, J. Am. Chem. Soc, 1997, 119, 4325-4329
52. M. Brenner, Pept, Proc. Eur. Pept. Symp, 8th, 1967, 1-7
53. D. S. Kemp, Biopolymers, 1981, 20, 1793-1804
54. C.-F. Liu, J. P. Tam, J. Am. Chem. Soc, 1994, 116, 4149-4153
55. T. M. Hackeng, C. M. Mounier, C. Bon, P. E. Dawson, J. H. Griffin, S. B. H. Kent, Proc. Natl. Acad. Sci. U. S. A, 1997, 94, 7845-7850
56. D. W. Low, M. G. Hill, M. R. Carrasco, S. B. Kent, P. Botti, Proc. Natl. Acad. Sci. U. S. A, 2001, 98, 6554-6559
57. D. S. Kemp, R. I. Carey, J. Org. Chem, 1993, 58, 2216-2222
58. D. Fiset, A. B. Charette, RSC Adv, 2012, 2, 5502-5505
59. W. C. Chan, B. W. Bycroft, D. J. Evans, P. D. White, J. Chem. Soc, Chem. Commun, 1995, 2209-2210