Recent Strategies for Stereoselective Sialylation and Their Application to the Synthesis of Oligosialosides

Trends in Glycoscience and Glycotechnology

Volumn 23, Issue 131, 2011, Pages 111-121

  Hanashima, Shinya ^a  

^a RIKEN   (Japan)

Author keywords

glycosylation; polysialic acid; sialic acid; stereoselectivity

Indexed keywords

EID: 84922685310     PISSN: 09157352     EISSN: None     Source Type: Journal    
DOI: 10.4052/tigg.23.111     Document Type: Article

References (58)

1. Angata, T., and Varki, A. (2002) Chem. Rev. 102, 439–469.
2. Ando, T., Ando, H., and Kiso, M. (2001) Trends Glycosci. Glycotechnol. 13, 573–586.
3. Angata, K., and Fukuda, M. (2010) Methods Enzymol. 479, 25–36.
4. Devi, S. J. N., Schneerson, R., Egan, W., Vann, W. F., Robbins, J.B., and Shiloach, J. (1991) Infect. Immun. 59, 732–736.
5. Jennings, H. J., Roy, R., and Michon, F. (1985) J. Immunol. 134, 2651–2657.
6. Ferrero, M. A., and Aparicio, L. R. (2010) Appl. Microbiol. Biotechnol. 86, 1621–1635.
7. Lee, Y. S., Kubota, A., Ishiwata, A., and Ito, Y. (2011) Tetrahedron Lett. 52, 418–421.
8. Watson, D. C., Leclerc, S., Wakarchuk, W. W., and Young, N. M. (2011) Glycobiology 21, 99–108.
9. Tsvetkov, Y. E., Shashkov, A. S., Knirel, Y. A., and Zähringer, U. (2001) Carbohydr. Res. 335, 221–243.
10. Kitazume, S., Kitajima, K., Inoue, S., Troy, F. A. II, Cho, J.-W., Lennarz, W. J., and Inoue, Y. (1994) J. Biol. Chem. 269, 22712–22718.
11. Chen, X., and Varki, A. (2010) ACS Chem. Biol. 5, 163–176.
12. Boons, G.-J., and Demchenko, A. V. (2000) Chem. Rev. 100, 4539–4566.
13. Halcomb, R. L., and Chappell, M. D. (2002) J. Carbohydr. Chem. 21, 723–768.
14. Ando, H., and Imamura, A. (2004) Trends Glycosci. Glycotechnol. 16, 293–303.
15. Takahashi, T., Tsukamoto, H., and Yamada, H. (1997) Tetrahedron Lett. 38, 8223–8226.
16. Ishiwata, A., and Ito, Y. (2003) Synlett 1339–1343.
17. Haberman, J. M., and Gin, D. Y. (2001) Org. Lett. 3, 1665–1668.
18. Haberman, J. M., and Gin, D. Y. (2003) Org. Lett. 5, 2539–2541.
19. Okamoto, R., Souma, S., and Kajihara, Y. (2008) J. Org. Chem. 73, 3460–3466.
20. Hanashima, S., Akai, S., and Sato, K. (2008) Tetrahedron Lett. 49, 5111–5114.
21. Demchenko, A. V., and Boons, G.-J. (1998) Tetrahedron Lett. 39, 3065–3068.
22. De Meo, C., Demchenko, A. V., and Boons, G.-J. (2001) J. Org. Chem. 66, 5490–5497.
23. Lin, C.-C., Huang, K.-T., and Lin, C.-C. (2005) Org. Lett. 7, 4169–4172.
24. Yu, C.-S., Niikura, K., Lin, C.-C., and Wong, C.-H. (2001) Angew. Chem., Int. Ed. 40, 2900–2903.
25. Tanaka, K., Goi, T., and Fukase, K. (2005) Synlett 2958–2962.
26. Ikeda, K., Miyamoto, K., and Sato, M. (2007) Tetrahedron Lett. 48, 7431–7435.
27. Tanaka, H., Adachi, M., and Takahashi, T. (2005) Chem. Eur. J. 11, 849–862.
28. Ando, H., Koike, Y., Ishida, H., and Kiso, M. (2003) Tetrahedron Lett. 44, 6883–6886.
29. Tanaka, H., Nishiura, Y., Adachi, M., and Takahashi, T. (2006) Heterocycles 67, 107–112.
30. Hanashima, S., Castagner, B., Esposito, D., Nokami, T., and Seeberger, P. H. (2007) Org. Lett. 9, 1777–1779.
31. Hanashima, S., and Seeberger, P. H. (2007) Chem. Asian J. 2, 1447–1459.
32. Tanaka, S., Goi, T., Tanaka, K., and Fukase, K. (2007) J. Carbohydr. Chem. 26, 369–394.
33. Tanaka, K., Fujii, Y., Tokimoto, H., Mori, Y., Tanaka, S., Bao, G.-m., Siwu, E. R. O., Nakayabu, A., and Fukase, K. (2009) Chem. Asian J. 4, 574–580.
34. Lin, C.-C., Adak, A. K., Horng, J.-C., and Lin, C.-C. (2009) Tetrahedron 65, 4714–4725.
35. Tanaka, H., Nishiura, Y., and Takahashi, T. (2006) J. Am. Chem. Soc. 128, 7124–7125.
36. Crich, D., and Li, W. (2007) J. Org. Chem. 72, 7794–7797.
37. Farri, M. D., and De Meo, C. (2007) Tetrahedron Lett. 48, 1225–1227.
38. Kanie, O., Kiso, M., and Hasegawa, A. (1988) J. Carbohydr. Chem. 7, 501–506.
39. Schmidt, R. R., Behrendt, M., and Toepfer, A. (1990) Synlett, 694–696.
40. Tanaka, H., Nishiura, Y., and Takahashi, T. (2008) J. Am. Chem. Soc. 130, 17244–17245.
41. Tanaka, H., Nishiura, Y., and Takahashi, T. (2009) J. Org. Chem. 74, 4383–4386.
42. Tanaka, H., Tateno, Y., Nishiura, Y., and Takahashi, T. (2008) Org. Lett. 10, 5597–5600.
43. Crich, D., and Chandrasekhar, N. (2010) Angew. Chem. Int. Ed. 49, 3049–3052.
44. De Meo, C., and Priyadarshani, U. (2008) Carbohydr. Res. 343, 1540–1552.
45. Hanashima, S., Sato, K., Ito, Y., and Yamaguchi, Y. (2009) Eur. J. Org. Chem. 4215–4220.
46. Hanashima, S., Yamaguchi, Y., Ito, Y., and Sato, K. (2009) Tetrahedron Lett. 50, 6150–6153.
47. Hsu, C.-H., Chu, K.-C., Lin, Y.-S., Han, J.-L., Peng, Y.-S., Ren, C.-T., Wu, C.-Y., and Wong, C.-H. (2010) Chem. Eur. J. 16, 1754–1760.
48. Kanie, O., Ito, Y., and Ogawa, T. (1994) J. Am. Chem. Soc. 116, 12073–12074.
49. Ando, H., Koike, Y., Koizumi, S., Ishida, H., and Kiso, M. (2005) Angew. Chem. Int. Ed. 44, 6759–6763.
50. Tanaka, H., Ando, H., Ishida, H., Kiso, M., Ishihara, H., and Koketsu, M. (2009) Tetrahedron Lett. 50, 4478–4481.
51. Ando, H., Ishida, H., and Kiso, M. (2010) Methods Enzymol. 478, 521–540.
52. Hasegawa, A., Uchimira, A., Ishida, H., and Kiso, M. (1995) Biosci. Biotechnol. Biochem. 59, 1091–1094.
53. Hanashima, S., Tomiya, T., Ishikawa, D., Akai, S., and Sato, K. (2009) Carbohydr. Res. 344, 959–965.
54. McAuliffe, J. C., Rabuka, D., and Hindsgaul, O. (2002) Org. Lett. 4, 3067–3069.
55. Fan, G.-T., Lee, C.-C., Lin, C.-C., and Fang, J.-M. (2002) J. Org. Chem. 67, 7565–7568.
56. Ren, C.-T., Chen, C.-S., Yu, Y.-P., Tsai, Y.-F., Lin, P.-Y., Chen, Y.-J., Zou, W., and Wu, S.-H. (2003) Chem. Eur. J. 9, 1085–1095.
57. Hanashima, S., Ishikawa, D., Akai, S., and Sato, K. (2009) Carbohydr. Res. 344, 747–752.
58. Tamai, H., Ando, H., Tanaka, H., Hosoda-Yabe, R., Yabe, T., Ishida, H., and Kiso, M. (2011) Angew. Chem. Int. Ed. 50, 2330–2333.