Sequential glycoproteins: Practical method for the synthesis of antifreeze glycoprotein models containing base labile groups

Macromolecules

Volumn 37, Issue 18, 2004, Pages 6771-6779

  Tachibana, Yuki ^a   Monde, Kenji ^a   Nishimura, Shin Ichiro ^a,b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFREEZE SOLUTIONS; CARBOHYDRATES; CHEMICAL REACTIONS; HYDROGEN BONDS; MATHEMATICAL MODELS; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYPEPTIDES; SYNTHESIS (CHEMICAL);

BIOLOGICAL FUNCTIONS; CARBOHYDRATE RESIDUES; GLYCOPROTEINS; MACROMONOMERS;

PROTEINS;

EID: 4544301430     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma049756z     Document Type: Article

References (36)

1. Denda-Nagai, K.; Irimura, T. Glycoconjugate J. 2000, 17, 649-658.
2. Dwek, R. A. Chem. Rev. 1996, 96, 683-720.
3. Lowe, J. B. Cell 2001, 104, 809-812.
4. (a) Grogan, M. J.; Pratt, M. R.; Marcaurelle, L. A.; Bertozzi, C. R. Annu. Rev. Biochem. 2002, 71, 593-634.
5. (b) Brocke, C.; Kunz, H. Bioorg. Med. Chem. 2002, 3085-3112.
6. (c) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 4495-4537.
7. (a) Tsuda, T.; Nishimura, S.-I. Chem. Commun. 1996, 2779-2780.
8. (b) Tachibana, Y.; Matsubara, N.; Nakajima, F.; Tsuda, T.; Tsuda, S.; Monde, K.; Nishimura, S.-I. Tetrahedron 2002, 58, 10213-10224.
9. Tachibana, Y.; Fletcher, G. L.; Fujitani, N.; Tsuda, S.; Monde, K.; Nishimura, S.-I. Angew. Chem., Int. Ed. 2004, 43, 856-862.
10. Yeh, Y.; Feeney, R. E. Chem. Rev. 1996, 96, 601-607.
11. Maeji, N. J.; Inoue, Y.; Chujo, R. Biopolymers 1987, 26, 1753-1767.
12. Butenhof, K. J.; Gerken, T. A. Biochemistry 1993, 32, 2650-2663.
13. Naganagowda, G. A.; Gururaja, T. L.; Levine, M. J. J. Biomol. Struct. Dyn. 1998, 16, 91-107.
14. Coltart, D. M.; Royyuru, A. K.; Williams, L. J.; Glunz, P. W.; Sames, D. ; Kuduk, S. D.; Schwarz, J. B.; Chen, X. T.; Danishefsky, S. J.; Live, D. H. J. Am. Chem. Soc. 2002, 124, 9833-9844.
15. Kiso, Y.; Kai, Y.; Yajima, K. Chem. Pharm. Bull 1973, 21, 2507-2510.
16. Kunishima, M.; Kawachi, C.; Hioki, K.; Terao, K.; Tani, S. Tetrahedron 2001, 57, 1551-1558.
17. Fernandez-Mayoralas, A.; Marra, A.; Trumtel, M.; Veyrieres, A.; Sinäy, P. Carbohydr. Res. 1989, 188, 81-95.
18. David, S.; Hanessian, S. Tetrahedron 1985, 41, 643-663.
19. Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189-4192.
20. Suzuki, K.; Maeta, H.; Matsumoto, T. Tetrahedron Lett. 1989, 30, 4853-4856.
21. Shioiri, T.; Ninomiya, K.; Yamada, S.-I. J. Am. Chem. Soc. 1972, 94, 6203-6205.
22. Belleau, B.; Malek, G. J. Am. Chem. Soc. 1968, 90, 651-652.
23. Kunishima, M.; Kawachi, C.; Morita, J.; Terao, K.; Iwasaki, F.; Tani, S. Tetrahedron 1999, 55, 13159-13170.
24. Kunishima, M.; Kitao, A.; Kawachi, C.; Watanabe, Y.; Iguchi, S.; Hioki, K.; Tani, S. Chem. Pharm. Bull. 2002, 50(4), 549-55.
25. Bodanszky, M.; Tolle, J. C.; Gardner, J. D.; Walker, M. D.; Mutt, V. Int. J. Peptide Protein Res. 1980, 16, 402-411.
26. Dolence, E. K.; Lin, C.-E.; Miller, M. J. J. Med. Chem. 1991, 34, 956-968.
27. Sames, D.; Chen, X. T.; Danishefsky, S. J. Nature (London) 1997, 389, 587-591.
28. Manabe, S.; Marui, Y.; Ito, Y. Chem.-Eur. J. 2003, 9, 1435-1447.
29. Raymond, J. A.; DeVries, A. L. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 2589-2593.
30. Bush, C. A.; Feeney, R. E.; Osuga, D. T.; Ralapati, S.; Yeh, Y. Int. J. Pept. Protein Res. 1981, 17, 125-129.
31. Nakahara, Y.; Iijima, H.; Sibayama, S.; Ogawa, T. Carbohydr. Res. 1991, 216, 211-215.
32. Mukaiyama, T.; Mural, Y.; Shoda, S.-I. Chem. Lett. 1981, 431-432.
33. Elofsson, M.; Salvador, L. A.; Kihlberg, J. Tetrahedron 1997, 53, 369-390.
34. Lubineau, A.; Augé, C.; Goff, N. L.; Narvor, C. L. Carbohydr. Res. 1998, 305, 501-509.
35. It should be noted that MALDI-TOF MS of large glycopeptides having O-glycans seems to be difficult due to instability of O-glycoside linkage between GalNAc (GlcNAc) and Thr (Ser) in these molecules. See for example: (a) Gallego, R. G.; Dudziak, G.; Kragl, U.; Wandrey, C.; Kamerling, J. P.; Vliegenthart, J. F. G. Biochimie 2003, 85, 275-286. (b) Kurogochi, M.; Matsushita, T.; Nishimura, S.-I. Angew. Chem., Int. Ed., in press.
36. It should be noted that MALDI-TOF MS of large glycopeptides having O-glycans seems to be difficult due to instability of O-glycoside linkage between GalNAc (GlcNAc) and Thr (Ser) in these molecules. See for example: (a) Gallego, R. G.; Dudziak, G.; Kragl, U.; Wandrey, C.; Kamerling, J. P.; Vliegenthart, J. F. G. Biochimie 2003, 85, 275-286. (b) Kurogochi, M.; Matsushita, T.; Nishimura, S.-I. Angew. Chem., Int. Ed., in press.