Chemical protein synthesis by kinetically controlled ligation of peptide O-esters

ChemBioChem

Volumn 11, Issue 4, 2010, Pages 511-515

  Zheng, Ji Shen ^a   Cui, Hong Kui ^a   Fang, Ge Min ^a   Xi, Wei An ^a   Liu, Lei ^a  

^a BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; CYSTEINE; ESTER DERIVATIVE; GLYCINE; GLYCOPROTEIN; LEUCINE; PEPTIDE; PROLINE; PROTEIN NAPIN; THIOESTER; UNCLASSIFIED DRUG; VALINE; VEGETABLE PROTEIN;

AMINO TERMINAL SEQUENCE; ARTICLE; CARBOXY TERMINAL SEQUENCE; CHEMICAL REACTION KINETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ONE POT SYNTHESIS; PEPTIDE ANALYSIS; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN ASSEMBLY; PROTEIN EXPRESSION; PROTEIN MODIFICATION; PROTEIN STRUCTURE; PROTEIN SYNTHESIS; SOLID PHASE SYNTHESIS;

AMINO ACID SEQUENCE; ESTERS; MOLECULAR SEQUENCE DATA; PEPTIDES; PROTEINS; SULFHYDRYL COMPOUNDS;

EID: 77149155649     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.200900789     Document Type: Article

References (72)

1. a) P. E. Dawson, S. B. H. Kent, Annu. Rev. Biochem. 2000, 69, 923;
2. b) B. L. Nilsson, M. B. Soellner, R. T. Raines, Annu. Rev. Biophys. Biomol. Struct. 2005, 34, 91;
3. c) C. Haase, O. Seitz, Angew. Chem. 2008, 120, 1575;
4. Angew. Chem. Int. Ed. 2008, 47, 1553;
5. d) S. B. H. Kent, Chem. Soc. Rev. 2009, 38, 338.
6. a) A. Brik, E. Keinan, P. E. Dawson, J. Org. Chem. 2000, 65, 3829;
7. b) D. Bang, N. Chopra, S. B. H. Kent, J. Am. Chem. Soc. 2004, 126, 1377;
8. c) D. Bang, S. B. H. Kent, Angew. Chem. 2004, 116, 2588;
9. Angew. Chem. Int. Ed. 2004, 43, 2534;
10. d) D. Bang, S. B. H. Kent, Proc. Natl. Acad. Sci. USA 2005, 102, 5014;
11. e) S. Ingale, T. Buskas, G. J. Boons, Org. Lett. 2006, 8, 5785;
12. f) E. C. B. Johnson, T. Durek, S. B. H. Kent, Angew. Chem. 2006, 118, 3361;
13. Angew. Chem. Int. Ed. 2006, 45, 3283;
14. g) E. C. B. Johnson, E. Malito, Y. Shen, D. Rich, W. J. Tang, S. B. H. Kent, J. Am. Chem. Soc. 2007, 129, 11480;
15. h) R. K. McGinty, J. Kim, C. Chatterjee, R. G. Roeder, T. W. Muir, Nature 2008, 453, 812;
16. i) B. L. Pentelute, Z. P. Gates, J. L. Dashnau, J. M. Vanderkooi, S. B. H. Kent, J. Am. Chem. Soc. 2008, 130, 9702.
17. a) L. E. Canne, A. R. Ferred Amare, S. K. Burley, S. B. H. Kent, J. Am. Chem. Soc. 1995, 117, 2998;
18. b) L. E. Canne, P. Botti, R. J. Simon, Y. J. Chen, E. A. Dennis, S. B. H. Kent, J. Am. Chem. Soc. 1999, 121, 8720;
19. c) Z. W. Miao, J. P. Tam, J. Am. Chem. Soc. 2000, 122, 4253;
20. d) J. P. Tam, Q. T. Yu, J. L. Yang, J. Am. Chem. Soc. 2001, 123, 2487.
21. a) D. Bang, B. L. Pentelute, S. B. H. Kent, Angew. Chem. 2006, 118, 4089;
22. Angew. Chem. Int. Ed. 2006, 45, 3985;
23. b) T. Durek, V. Y. Torbeev, S. B. H. Kent, Proc. Natl. Acad. Sci. USA 2007, 104, 4846;
24. c) V. Y. Torbeev, S. B. H. Kent, Angew. Chem. 2007, 119, 1697;
25. Angew. Chem. Int. Ed. 2007, 46, 1667;
26. d) Q. Wan, S. J. Danishefsky, Angew. Chem. 2007, 119, 9408;
27. Angew. Chem. Int. Ed. 2007, 46, 9248;
28. e) D. Crich, I. Sharma, Angew. Chem. 2009, 121, 7727;
29. Angew. Chem. Int. Ed. 2009, 48, 7591.
30. a) H. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn. 1991, 64, 111;
31. b) M. Schnc̈lzer, P. Alewood, A. Jones, D. Alewood, S. B. H. Kent, Int. J. Pept. Res. Ther. 2007, 13, 31;
32. c) T. W. Muir, D. Sondhi, P. A. Cole, Proc. Natl. Acad. Sci. USA 1998, 95, 6705;
33. d) 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;
34. e) R. Ingenito, E. Bianchi, D. Fattori, A. Pessi, J. Am. Chem. Soc. 1999, 121, 11369;
35. f) A. Sewing, D. Hilvert, Angew. Chem. 2001, 113, 3503;
36. Angew. Chem. Int. Ed. 2001, 40, 3395;
37. g) A. R. Mezo, R. P. Cheng, B. Imperiali, J. Am. Chem. Soc. 2001, 123, 3885;
38. h) J. Brask, F. Albericio, K. J. Jensen, Org. Lett. 2003, 5, 2951;
39. i) J. A. Camarero, B. J. Hackel, J. J. De Yoreo, A. R. Mitchell, J. Org. Chem. 2004, 69, 4145;
40. j) C. Dose, O. Seitz, Org. Lett. 2005, 7, 4365;
41. k) N. Ollivier, J. B. Behr, O. El-Mahdi, A. Blanpain, O. Melnyk, Org. Lett. 2005, 7, 2647;
42. l) T. Kawakami, M. Sumida, K. Nakamura, T. Vorherr, S. Aimoto, Tetrahedron Lett. 2005, 46, 8805;
43. m) S. Mezzato, M. Schaffrath, C. Unverzagt, Angew. Chem. 2005, 117, 1677; Angew. Chem. Int. Ed. 2005, 44, 1650;
44. n) F. Nagaike, Y. Onuma, C. Kanazawa, H. Hojo, A. Ueki, Y. Nakahara, Y. Nakahara, Org. Lett. 2006, 8, 4465;
45. o) T. Kawakami, S. Aimoto, Tetrahedron Lett. 2007, 48, 1903;
46. p) F. Mende O. Seitz, Angew. Chem. 2007, 119, 4661;
47. Angew. Chem. Int. Ed. 2007, 46, 4577;
48. q) N. Yamamoto, Y. Tanabe, R. Okamoto, P. E. Dawson, Y. Kajihara, J. Am. Chem. Soc. 2008, 130, 501;
49. r) S. Ficht, R. J. Payne, R. T. Guy, C. H. Wong, Chem. Eur. J. 2008, 14, 3620;
50. s) D. Lelìvre, P. Barta, V. Aucagne, A. F. Delmas, Tetrahedron Lett. 2008, 49, 4016;
51. t) T. Kawakami, S. Aimoto, Tetrahedron 2009, 65, 3871.
52. a) D. Bang, B. L. Pentelute, Z. P. Gates, S. B. H. Kent, Org. Lett. 2006, 8, 1049;
53. b) J. B. Blanco-Canosa, P. E. Dawson, Angew. Chem. 2008, 120, 6957;
54. Angew. Chem. Int. Ed. 2008, 47, 6851;
55. c) H. Hojo, Y. Murasawa, H. Katayama, T. Ohira, Y. Nakahara, Y. Nakahara, Org. Biomol. Chem. 2008, 6, 1808;
56. d) A. P. Tofteng, K. Sørensen, K. W. Conde-Frieboes, T. Hoeg-Jensen, K. J. Jensen, Angew. Chem. 2009, 121, 7547;
57. Angew. Chem. Int. Ed. 2009, 48, 7411.
58. a) J. D. Warren, J. S. Miller, S. J. Keding, S. J. Danishefsky, J. Am. Chem. Soc. 2004, 126, 6576;
59. b) G. Chen, J. D. Warren, J. H. Chen, B. Wu, Q. Wan, S. J. Danishefsky, J. Am. Chem. Soc. 2006, 128, 7460;
60. c) B. Wu, J. H. Chen, J. D. Warren, G. Chen, Z. H. Hua, S. J. Danishefsky, Angew. Chem. 2006, 118, 4222;
61. Angew. Chem. Int. Ed. 2006, 45, 4116;
62. d) G. Chen, Q. Wan, Z. Tan, C. Kan, Z. Hua, K. Ranganathan, S. J. Danishefsky, Angew. Chem. 2007, 19, 7527;
63. Angew. Chem. Int. Ed. 2007, 46, 7383;
64. e) Q. Wan, J. Chen, Y. Yuan, S. J. Danishefsky, J. Am. Chem. Soc. 2008, 130, 15814;
65. f) Z. Tan, S. Shang, T. Halkina, Y. Yuan, S. J. Danishefsky, J. Am. Chem. Soc. 2009, 131, 5424.
66. P. Botti, S. Manganiello, H. Gaertner, Org. Lett. 2004, 6, 4861.
67. a) A. P. Tofteng, K. J. Jensen, T. Hoeg-Jensen, Tetrahedron Lett. 2007, 48, 2105;
68. b) E. A. George, R. P. Novick, T. W. Muir, J. Am. Chem. Soc. 2008, 130, 4914;
69. c) K. P. Chiang, M. S. Jensen, R. K. McGinty, T. W. Muir, Chem-BioChem 2009, 10, 2182.
70. a) E. C. B. Johnson, S. B. H. Kent, J. Am. Chem. Soc. 2006, 128, 6640;
71. b) E. Wieczerzak, R. Hamel Jr. , V. Chabot, V. Aimez, M. Grandbois, P. G. Charette, E. Escher, Biopolymers 2008, 90, 415.
72. G. M. Neumann, R. Condron, I. Thomas, G. M. Polya, Biochim. Biophys. Acta 1996, 1295, 23.