Chemical Synthesis of O-Glycosylated Human Interleukin-2 by the Reverse Polarity Protection Strategy

Angewandte Chemie - International Edition

Volumn 54, Issue 28, 2015, Pages 8226-8230

  Asahina, Yuya ^a   Komiya, Shinobu ^b   Ohagi, Ami ^b   Fujimoto, Rina ^b   Tamagaki, Hiroko ^a   Nakagawa, Katsuhiro ^c   Sato, Takashi ^c   Akira, Shizuo ^c   Takao, Toshifumi ^a   Ishii, Akira ^b   Nakahara, Yoshiaki ^b   Hojo, Hironobu ^a  

^a OSAKA UNIVERSITY   (Japan)

^b TOKAI UNIVERSITY   (Japan)

^c OSAKA UNIVERSITY   (Japan)

Author keywords

glycoprotein; ligation; peptides; synthesis design; synthetic methods

Indexed keywords

BIOACTIVITY; GLYCOPROTEINS; PEPTIDES;

C-TERMINAL REGIONS; HUMAN INTERLEUKIN; ISO-ELECTRIC POINTS; LIGATION; REVERSE POLARITY PROTECTION; SOLID-PHASE METHOD; SYNTHESIS DESIGN; SYNTHETIC METHODS;

SYNTHESIS (CHEMICAL);

GLYCOPROTEIN; INTERLEUKIN 2; INTERLEUKIN 2, GLYCOSYLATED; PEPTIDE;

ANALOGS AND DERIVATIVES; CHEMISTRY; HUMAN; SYNTHESIS;

GLYCOPROTEINS; HUMANS; INTERLEUKIN-2; PEPTIDES;

EID: 84933497267     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201501847     Document Type: Article

References (28)

1. P. E. Dawson, T. W. Muir, I. Clark-Lewis, S. B. H. Kent, Science 1994, 266, 776-779
2. P. E. Dawson, S. B. H. Kent, Annu. Rev. Biochem. 2000, 69, 923-960.
3. H. Hojo, S. Aimoto, Bull. Chem. Soc. Jpn. 1991, 64, 111-117
4. S. Aimoto, Biopolymers 1999, 51, 247-265
5. H. Hojo, Y. Murasawa, H. Katayama, T. Ohira, Y. Nakahara, Y. Nakahara, Org. Biomol. Chem. 2008, 6, 1808-1813.
6. S. B. H. Kent, Chem. Soc. Rev. 2009, 38, 338-351
7. C. Unverzagt, Y. Kajihara, Chem. Soc. Rev. 2013, 42, 4408-4420.
8. K. Mandal, M. Uppalapati, D. Ault-Riche, J. Kenney, J. Lowitz, S. S. Sidhu, S. B. H. Kent, Proc. Natl. Acad. Sci. USA 2012, 109, 14779-14784.
9. H. Hojo, H. Tanaka, M. Hagiwara, Y. Asahina, A. Ueki, H. Katayama, Y. Nakahara, A. Yoneshige, J. Matsuda, Y. Ito, Y. Nakahara, J. Org. Chem. 2012, 77, 9437-9446.
10. Y. Sohma, M. Sasaki, Y. Hayashi, T. Kimura, Y. Kiso, Chem. Commun. 2004, 124-125
11. Y. Sohma, T. Yoshiya, A. Taniguchi, T. Kimura, Y. Hayashi, Y. Kiso, Biopolymers 2007, 88, 253-262.
12. T. Taniguchi, H. Matsui, T. Fujita, C. Takaoka, N. Kashima, R. Yoshimoto, J. Hamuro, Nature 1983, 302, 305-310.
13. M. R. Arkin, M. Randal, W. L. DeLano, J. Hyde, T. N. Luong, J. D. Oslob, D. R. Raphael, L. Taylor, J. Wang, R. S. McDowell, J. A. Wells, A. C. Braisted, Proc. Natl. Acad. Sci. USA 2003, 100, 1603-1608.
14. R. Garner, G. T. Young, Nature 1969, 222, 177-178
15. J. Rizo, F. Albericio, G. Romero, C. Garcia-Echeverria, J. Claret, C. Muller, E. Giralt, E. Pedroso, J. Org. Chem. 1988, 53, 5386-5390.
16. J. L. Lauer, C. G. Fields, G. B. Fields, Lett. Pept. Sci. 1995, 1, 197-205
17. T. Michels, R. Dolling, U. Haberkorn, W. Mier, Org. Lett. 2012, 14, 5218-5221.
18. H. Hojo, Y. Onuma, Y. Akimoto, Y. Nakahara, Y. Nakahara, Tetrahedron Lett. 2007, 48, 25-28.
19. D. F. Veber, W. J. Paleveda, Jr., Y. C. Lee, R. Hirschmann, J. Org. Chem. 1977, 42, 3286-3288.
20. Y. Asahina, S. Kamitori, T. Takao, N. Nishi, H. Hojo, Angew. Chem. Int. Ed. 2013, 52, 9733-9737
21. Angew. Chem. 2013, 125, 9915-9919
22. Y. Asahina, M. Kanda, A. Suzuki, H. Katayama, Y. Nakahara, H. Hojo, Org. Biomol. Chem. 2013, 11, 7199-7207.
23. L. Raibaut, P. Seeberger, O. Melnyk, Org. Lett. 2013, 15, 5516-5519.
24. Y. Asahina, K. Nabeshima, H. Hojo, Tetrahedron Lett. 2015, 56, 1370-1373.
25. Y. Asahina, R. Fujimoto, A. Suzuki, H. Hojo, J. Carbohydr. Chem. 2015, 34, 12-27.
26. S. B. Pollock, S. B. H. Kent, Chem. Commun. 2011, 47, 2342-2344
27. T. Nakamura, A. Shigenaga, K. Sato, Y. Tsuda, K. Sakamoto, A. Otaka, Chem. Commun. 2014, 50, 58-60.
28. P. Sengupta, K. Meena, R. Mukherjee, S. K. Jain, K. Maithal, Indian J. Biochem. Biophys. 2008, 45, 91-97.