Chemical synthesis of proteins

Progress in Chemistry

Volumn 19, Issue 12, 2007, Pages 1866-1882

  Li, Juan ^a,b   Zhng, Jishen ^a   Shen, Fei ^a   Fang, Gemin ^a   Guo, Qingxiang ^b   Liu, Lei ^a,b  

^a TSINGHUA UNIVERSITY   (China)

^b UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

Cysteine; Glycoprotein; Lipidated protein; Peptide ligation; Thioester

Indexed keywords

EID: 38749083407     PISSN: 1005281X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (84)

1. Kochendoerfer G G, Kent S B H. Curr. Opin. Chem. Biol., 1999, 3 (6): 665-671
2. Wang L, Xie J M, Schultz P. Annu. Rev. Biophys. Biomol. Struct., 2006, 35: 225-249
3. Dawson P E, Muir T W, Kent S B H, et al. Science, 1994, 266 (5186): 776-779
4. Dawson P E, Kent S B H. Annu. Rev. Biochem., 2000, 69: 923-960
5. Ma Y, Zhao Y F. Chin. Sci. Bull., 2003, 48: 1-5
6. (Ma Y), (Zhao Y F). (Prog. Chem.), 2003, 15: 393-400
7. Wieland T B E, Bauer L, Schafer W, et al. Liebigs Ann. Chem., 1953, 583: 129-149
8. Bang D, Kent S B H. Angew. Chem. Int. Ed., 2004, 43 (19): 2534-2538
9. Bang D, Neeraj C, Kent S B H. J. Am. Chem. Soc., 2004, 126 (5): 1377-1383
10. Johnson E C B, Durek T, Kent S B H. Angew. Chem. Int. Ed., 2006, 45 (20): 3283-3287
11. Torbeev V Y, Kent S B H. Angew. Chem. Int. Ed., 2007, 46 (10): 1667-1670
12. Johnson E C B, Kent S B H. J. Am. Chem. Soc., 2006, 128 (20): 6640-6646
13. Hackeng T M, Griffin J H, Dawson P E. Proc. Nat. Acad. Sci. USA, 1999, 96 (18): 10068-10073
14. Yan L Z, Dawson P E. J. Am. Chem. Soc., 2001, 123 (4): 526-533
15. Pentelute B L, Kent S B H. Org. Lett., 2007, 9 (4): 687-690
16. Crich D, Banerjee A. J. Am. Chem. Soc., 2007, 129 (33): 10064-10065
17. Botti P, Carrasco M R, Kent S B H. Tetrahedron Lett., 2001, 42 (10): 1831-1833
18. Low D W, Hill M G, Kent S B H, et al. PNAS, 2001, 98 (12): 6554-6559
19. Offer J, Boddy C N C, Dawson P E. J. Am. Chem. Soc., 2002, 124(17): 4642-4646
20. Kemp D S, Buckler D R. Tetrahedron Lett., 1991, 32 (26): 3009-3012
21. Kawakami T, Aimoto S. Tetrahedron Lett., 2003, 44 (32): 6059-6061
22. Marinzi C, Offer J, Dawson P E, et al. Bioorgan. Med. Chem., 2004, 12 (10): 2749-2757
23. Johnson T, Quibell M, Sheppard R C. J. Pept. Sci., 1995, 1 (1): 11-25
24. Fournie Zaluski M C, Coric P, Roques B P, et al. J. Med. Chem., 1992, 35 (7): 1259-1266
25. Zuckermann R N, Kerr J M, Kent S B H, et al. J. Am. Chem. Soc., 1992, 114(26): 10646-10647
26. Tam J P, Yu Q T. Biopolymers, 1998, 46 (5): 319-327
27. Gieselman M D, Zhu Y T, van der Donk W A, et al. ChemBioChem, 2002, 3 (8): 709-716
28. Zhang L S, Tam J P. Tetrahedron Lett., 1997, 38 (1): 3-6
29. Botti P, Villain M, Gaertner H, et al. Org. Lett., 2004, 6 (26): 4861-4864
30. Manabe S, Sugioka T, Ito Y. Tetrahedron Lett., 2007, 48 (5): 849-853
31. Li X Q, Kawakami T, Aimoto S. Tetrahedron Lett., 1998, 39 (47): 8669-8672
32. Backes B J, Virgilio A A, Ellman J A. J. Am. Chem. Soc., 1996, 118 (12): 3055-3056
33. Shin Y, Winans K A, Bertozzi C R, et al. J. Am. Chem. Soc., 1999, 121 (50): 11684-11689
34. Ingenito R, Bianchi E, Pessi A, et al. J. Am. Chem. Soc., 1999, 121 (49): 11369-11374
35. Biancalana S, Hudson D, Thompson S A, et al. Lett. Pept. Sci., 2001, 7 (5): 291-297
36. Merkx R, van Haren M J, Liskamp R M J, et al. J. Org. Chem., 2007, 72 (12): 4574-4577
37. Berst F, Holmes A B, Murray P J, et al. Tetrahedron Lett., 2000, 41 (34): 6649-6653
38. Camarero J A, Hackel B J, Mitchell A R, et al. J. Org. Chem., 2004, 69 (12): 4145-4151
39. Barlett K N, Kolakowski R V, Williams L J, et al. Org. Lett., 2006, 8 (5): 823-826
40. He Y, Wilkins J P, Kiessling L L. Org. Lett., 2006, 8 (12): 2483-2485
41. Quaderer R, Hilvert D. Org. Lett., 2001, 3 (20): 3181-3184
42. Warren J D, Miller J S, Danishefsky S J, et al. J. Am. Chem. Soc., 2004, 126 (21): 6576-6578
43. Chen J H, Chen G, Danishefsky S J, et al. Tetrahedron Lett., 2006, 47 (46): 8013-8016
44. Chen J H, Warren J D, Danishefsky S J, et al. Tetrahedron Lett., 2006, 47 (12): 1969-1972
45. Wu B, Chen J H, Danishefsky S J, et al. Angew. Chem. Int. Ed., 2006, 45 (25): 4116-4125
46. Kawakami T, Sumida M, Aimoto S, et al. Tetrahedron Lett., 2005, 46 (50): 8805-8807
47. Nakamura K, Mori H, Aimoto S, et al. Int. J. Pept. Res. Ther., 2007, 13 (1/2): 191-202
48. Kawakami T, Aimoto S. Tetrahedron Lett., 2007, 48 (11): 1903-1905
49. Ohta Y, Itoh S, Otaka A, et al. Org. Lett., 2006, 8 (3): 467-470
50. Hojo H, Onuma Y, Nakahara Y, et al. Tetrahedron Lett., 2007, 48 (1): 25-28
51. Hendrickson J B. J. Am. Chem. Soc., 1977, 99 (16): 5439-5450
52. Bang D, Pentelute B L, Kent S B H. Angew. Chem. Int. Ed., 2006, 45 (24): 3985-3988
53. Kent S B H. Annu. Rev. Biochem., 1988, 57: 957-984
54. Canne L E, Botti P, Kent S B H, et al. J. Am. Chem. Soc., 1999, 121 (38): 8720-8727
55. Kochendoerfer G G, Chen S Y, Kent S B H, et al. Science, 2003, 299 (5608): 884-887
56. Schnölzer M, Alewood P, Kent S B H, et al. Int. J. Pept. Protein Res., 1992, 40: 180-193
57. Rose K, Vizzavona J. J. Am. Chem. Soc., 1999, 121 (30): 7034-7038
58. Resh M D. BBA-Mol. Cell Res., 1999, 1451 (1): 1-16
59. Porter J A, Young K E, Beachy P A. Science, 1996, 274 (5285): 255-259
60. Zhang F L, Casey P J. Annu. Rev. Biochem., 1996, 65: 241-269
61. Casey P J. Science, 1995, 268 (5208): 221-225
62. Guo Y T, Li Y M, Zhao Y F. Chin. J. Org. Chem., 2004, 24 (7): 722-727
63. Brunsveld L, Kuhlmann J, Waldmann H, et al. Angew. Chem. Int. Ed., 2006, 45 (40): 6622-6646
64. Takai Y, Sasaki T, Matozaki T. Physiol. Rev., 2001, 81 (1): 153-208
65. Woo Y H, Mitchell A R, Camarero J A. Int. J. Pept. Res. Ther., 2007, 13 (1/2): 181-190
66. Kragol G, Lumbierres M, Waldmann H, et al. Angew. Chem. Int. Ed., 2004, 43 (43): 5839-5842
67. Liu L, Bennett C S, Wong C H. Chem. Commun., 2006, 21-33
68. Hojo H, Nakahara Y. Biopolymers, 2007, 88 (2): 308-324
69. Macmillan D, Daines A M. Curr. Med. Chem., 2003, 10 (24): 2733-2773
70. Sears P, Wong C H. Science, 2001, 291 (5512): 2344-2350
71. Davis B G. Chem. Rev., 2002, 102 (2): 579-601
72. Thayer D A, Yu H N, Wong C H, et al. Angew. Chem. Int. Ed., 2005, 44 (29): 4596-4599
73. Brik A, Ficht S, Wong C H. Curr. Opin. Chem. Biol., 2006, 10 (6): 638-644
74. David R, Richter M P O, Beck-Sickinger A G. Eur. J. Biochem., 2004, 271 (4): 663-677
75. Muir T W, Sondhi D, Cole P A. PNAS, 1998, 95 (12): 6705-6710
76. Severinov K, Muir T W. J. Biol. Chem., 1998, 273 (26): 16205-16209
77. Kohn M, Breinbauer R. Angew. Chem. Int. Ed., 2004, 43 (24): 3106-3116
78. Tolbert T J, Franke D, Wong C H. Bioorgan. Med. Chem., 2005, 13 (3): 909-915
79. Grandjean C, Boutonnier A, Mulard L A, et al. J. Org. Chem., 2005, 70 (18): 7123-7132
80. Brik A, Yang Y Y, Wong C H, et al. J. Am. Chem. Soc., 2006, 128 (17): 5626-5627
81. Brik A, Ficht S, Wong C H, et al. J. Am. Chem. Soc., 2006, 128 (46): 15026-15033
82. Yang Y Y, Ficht S, Wong C H, et al. J. Am. Chem. Soc., 2007, 129 (24): 7690-7701
83. Brik A, Wong C H. Chem. Eur. J., 2007, 13 (20): 5670-5675
84. Hsieh-Wilson L C. Nature, 2007, 445 (7123): 31-33