Recent progress in the synthetic methodologies of peptide thioesters

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 68, Issue 9, 2010, Pages 911-919

  Shigenaga, Akira ^a   Sato, Kohei ^a   Otaka, Akira ^a  

^a UNIVERSITY OF TOKUSHIMA   (Japan)

Author keywords

Acyl transfer; Expressed protein ligation; Fragment condensation; Native chemical ligation; Peptide synthesis; Peptide thioester; Protein synthesis; Protein thioester; Thioester method

Indexed keywords

ACYL TRANSFER; EXPRESSED PROTEIN LIGATION; FRAGMENT CONDENSATION; NATIVE CHEMICAL LIGATION; PEPTIDE SYNTHESIS; PROTEIN SYNTHESIS; THIOESTERS;

CONDENSATION; PEPTIDES;

SYNTHESIS (CHEMICAL);

EID: 78650356440     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.68.911     Document Type: Article

References (78)

1. C. P. R Hackenberger, D. Schwarzer, Angew. Chem. Int. Ed., 47, 10030(2008)
2. (a) H. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn., 64, 111 (1991);
3. (b) S. Aimoto, Biopolymers (Peptide Science), 51, 247(1999)
4. (a) P. E. Dawson, T. W. Muir, I. Clark-Lewis. S. B. H. Kent, Science. 266, 776(1994);
5. (b) NCL P. E. Dawson, S. B. H. Kent, Annu. Rev. Biochem., 69, 923(2000)
6. W. C. Chan, P. D. White, "Fmoc Solid Phase Peptide Synthesis" Oxford University Press, Oxford, 2000
7. V. T. Wieland, R Lamber, H. L. Lang, M. Gunther Schramm, Liebigs Ann. Chem., 597, 181(1956)
8. J. A. Camarero, A. R. Mitchell, Protein Pept. Lett., 12, 723 (2005)
9. S. Futaki, K. Sogawa, J. Maruyama, T. Asahara, M. Niwa, H. Hojo, Tetrahedron Lett., 38, 6237(1997)
10. (a)A. R Mezo, R. P. Cheng, B. Imperiali, J. Am. Chem. Soc., 123, 3885(2001);
11. (b) R von Eggelkraut-Gottanka A. Klose. A. G. Beck-Sickinger, M. Beyermann, Tetrahedron Lett., 44, 3551 (2003)
12. X. Li, T. Kawakami, S. Aimoto, Tetrahedron Lett., 39, 8669 (1998)
13. A. B. Clippingdale, C. J. Barrow, J. D. Wade, J. Pept. Sci., 6, 225(2000)
14. (a) K. Hasegawa, Y. L. Sha, J. K. Bang, T. Kawakami, K. Akaji, S. Aimoto, Lett. Pept. Sci., 8, 277(2002);
15. (b) H. Hojo, E. Haginoya Y. Matsumoto, Y. Nakahara, K. Nabeshima B. P. Toole. Y. Watanabe, Tetrahedron Lett., 44, 2961(2003)
16. (a) J. Alsina, K. J. Jensea, F. Albericio, G. Barany, Chem. Eur. J., 5, 2787(1999);
17. (b) U. Boas, Chem. Rev., 109, 2092(2009)
18. J. Alsina, T. S. Yokum, F. Albericio, G. Barany, J. Org. Chem., 64, 8761(1999)
19. J. Brask, F. Albericio, K. J. Jensen. Org. Lett., 5, 2951(2003)
20. A. Ishii, H. Hojo, Y. Nakahara, Y. Ito, Y. Nakahara. Biosci. Biotechnol. Biochem., 66, 225(2002)
21. (a) J. Tulla-Puche, G. Barany, J. Org. Chem., 69, 4101(2004);
22. (b) P. Wang, L. P. Miranda Int. J. Pept. Res. Ther., 11, 117 (2005);
23. (c) L. Li, P. Wang, Tetrahedron Lett., 48, 29(2007);
24. (d) S. Ficht, R J. Payne, R T. Guy, C.-H. Wong, Chem. Eur. J., 14, 3620 (2008);
25. (e) D. Lelievre, P. Barta, V. Aucagne. A. F. Delmas, Tetrahedron Lett., 49, 4016 (2008)
26. (a) D. Swinnen, D. Hilvert, Org. Lett., 2, 2439 (2000);
27. (b) A. Sewing. D. Hilvert, Angew. Chem. Int. Ed., 40, 3395(2001)
28. (a) J. D. Warren, J. S. Miller, S. J. Keding, S. J. Danishefsky, J. Am. Chem. Soc. 126, 6576(2004);
29. (b) Z. Tan, S. Shang, T. Halkina, Y. Yuan, S. J. Danishefsky, J. Am. Chem. Soc., 131, 5424(2009);
30. (c) Y. Yuan, J. Chen. Q. Wan, Z. Tan, G. Chen, C. Kan, S. J. Danishefsky, J. Am. Chem. Soc. 131. 5432(2009);
31. (d) C. Kan, J. D. Trzupek, B. Wu, Q, Wan. G. Chen, Z. Tan, Y. Yuan S. J. Danishefsky, J. Am. Chem. Soc. 131, 5438(2009);
32. (e) Danishefsky C. Kan, S. J. Danishefsky. Tetrahedron. 65, 9047(2009)
33. A. P. Tofteng, K. J. Jensen. T. Hoeg-Jensen, Tetrahedron Lett. 48, 2105(2007)
34. P. Botti, M. Villain, S. Maganiello, H. Gaertner. Org. Lett. 6, 4861(2004)
35. J.-S. Zheng, H.-K. Cui, G.-M. Fang, W.-X. Xi, L. Li, ChemBioChem, 11, 511(2010)
36. J. Kang, D. Macmillan, Org. Biomol. Chem., 8, 1993(2010)
37. R. Ingenito. E. Bianchi. D. Fattori, A. Pessi, J. Am. Chem. Soc. 121, 11369(1999)
38. Y. Shin K. A. Winans, B. J. Backes, S. B. H. Kent J. A. Ellman, C. R. Bertozzi, J. Am. Chem. Soc., 121, 11684(1999)
39. Y. He, J. P. Wilkins, L. L Kiessling, Org. Lett, 8, 2483(2006)
40. N. Ollivier. J.-B. Behr. O. El-Mahdi, A. Blanpain, O. Melnyk, Org. Lett. 7, 2647(2005)
41. S. Mezzato, M. Schaffrath, C. Unverzagt Angew. Chem. Int. Ed., 44, 1650(2005)
42. F. Mande. O. Seitz, Angew. Chem. Int. Ed., 46, 4577(2007)
43. S. Manabe, T. Sugioka Y. Ito. Tetrahedron Lett. 48, 849(2007)
44. J. A. Camarero, B. J. Hackel, J. J. de Yoreo, A. R Mitchell, J. Org. Chem., 69, 4145(2004)
45. T. J. Hogenauer, Q. Wang. A. K. Sanki. A. J. Gammoa C. H. L. Chu, C. M. Kaneshiro, Y. Kajihara K. Michael. Org. Biomol. Chem., 5, 759(2007)
46. J. B. Blanco-Canosa P. E. Dawsoa Angew. Chem. Int. Ed., 47, 6851(2008)
47. A. P. Tofteng, K. K. Sorensen, K. W. Conde-Frieboes, T. Hoeg-Jensen, K. J. Jensen, Angew. Chem. Int. Ed., 48, 7411 (2009)
48. J. Vizzavona F. Dick, T. Vorherr, Bioorg. Med. Chem. Lett., 12, 1963(2002)
49. (a) T. Kawakami. M. Sumida. K. Nakamura, T. Vorherr, S. Aimoto, Tetrahedron Lett. 46, 8805(2005);
50. (b) K. Nakamura M. Sumida T. Kawakami, T. Vorherr. A. Aimoto, Bull. Chem. Soc. Jpn., 79, 1773(2006):
51. (c) K. Nakamura. T. Kanao. T. Uesugi, T. Hara, T. Sato. T. Kawakami, S. Aimoto, J. Pept. Sci., 15, 731(2009)
52. F. Nagaike, Y. Onuma C. Kanazawa. H. Hojo. A. Ueki. Y. Nakahara Y. Nakahara Org. Lett. 8, 4465(2006)
53. (a) H. Hojo, Y. Onuma Y. Akimoto, Y. Nakahara Y. Nakahara Tetrahedron Lett. 48, 25(2007);
54. (b) C. Ozawa, H. Katayama H. Hojo. Y. Nakahara Y. Nakahara Org. Lett., 10, 3531(2008);
55. (c) H. Hojo, Y. Murasawa. H. Katayama, T. Ohira, Y. Nakahara Y. Nakahara, Org. Biomol. Chem., 6, 1808(2008);
56. (d) Y. Nakahara, I. Matsuo, Y. Ito. R. Ubagai. H. Hojo, Y. Nakahara Tetrahedron Lett. 51, 407(2010);
57. (e) H. Katayama H. Hojo, L Shimizu, Y. Nakahara Y. Nakahara Org. Biomol. Chem., 8, 1966-1972 (2010):
58. (f) L. A. Erlica K. S. A. Kumar, M. Haj-Yahya, P. E. Dawsoa, A. Brik. Org. Biomol. Chem., 8, 2392(2010)
59. Y. Ohta S. Itoh, A. Shigenaga S. Shintaku. N. Fujii, A. Otaka Org. Lett., 8, 467(2006)
60. (a) S. Tsuda, A. Shigenaga, K. Bando, A. Otaka Org. Lett., 11, 823(2009);
61. (b) A. Shigenaga, Y. Sumikawa, S. Tsuda, K. Sato, A. Otaka, Tetrahedron, 66, 3290(2010);
62. (c) K. Sato, Y. Sumikawa, A. Shigenaga, A. Otaka, manuscript in preparation.
63. (a) T. Kawakami. S. Aimoto. Chem. Lett., 36, 76(2007);
64. (b) T. Kawakami. S. Aimoto. Tetrahedron Lett. 48, 1903(2007);
65. (c) T. Kawakami, S. Aimoto, Tetrahedron, 65, 3871 (2009)
66. Y. Shimizu, A. Inoue, Y. Tomari, T. Suzuki, T. Yokogawa, K. Nishikawa, T. Ueda, Nat. Biotechnol., 19, 751(2001)
67. T. Kawakami, A. Ohta M. Ohuchi, H. Ashigai, H. Murakami, H. Suga, Nat. Chem. Biol., 5, 888 (2009)
68. bcPURE T. Higuchi, H. Suga J. Synth. Org. Chem., Jpn., 68, 217(2010)
69. (a) J. Kang, J. P. Richardson, D. Macmillaa Chem. Commun., 2009, 407;
70. (b) J. Kang, N. L. Reynolds, C. Tyrrell, J. R Dorin, D. Macmillan, Org. Biomol. Chem., 7, 4918(2009);
71. (c) J. P. Richardson, C-H. Chan, J. Blanc, M. Saadi, D. Macmillan Org. Biomol. Chem., 8, 1351(2010)
72. (a) T. W. Muir. D. Sondhi. P. A. Cole, Proc Natl. Acad. Sci. USA. 95, 6705(1998); EPL
73. (b) T. W. Muir, Annu. Rev. Biochem., 72, 249(2003);
74. (c) V. Muralidharan, T. W. Muir. Nat. Methods. 3, 429(2006);
75. (d) T. W. Muir. Biopolymers (Peptide Science), 90, 743(2008)
76. Y. Anraku, Y. Satow, Proc. Jpn. Acad., Ser. B. 85, 409(2009)
77. S. Chong, F. B. Mersha, D. G. Comb, M. E. Scott D. Landry, L. M. Vence, F. B. Perler, J. Benner, R. B. Kucera. C. A. Hirvonen, J. J. Pelletier, H. Paulus, M.-Q. Xu, Gene, 192, 271 (1997)
78. X-H. Tan, A. Wirjo. C-.F. Liu, ChemBioChem. 8, 1512 (2007)