Development of novel glycosyl donors for 1,2-cis glycosylation reaction for amino sugar and synthesis of anti-Helicobacter pylori oligosaccharide

Trends in Glycoscience and Glycotechnology

Volumn 20, Issue 114, 2008, Pages 187-202

  Manabe, Shino ^a   Ishii, Kazuyuki ^a   Ito, Yukishige ^a  

^a NONE

Author keywords

Amino sugar; Anti Helicobacter pylori oligosaccharide; Glycosylaion reaction; Selectivity; Trans carbamate having donor

Indexed keywords

HELICOBACTER PYLORI;

EID: 57649136528     PISSN: 09157352     EISSN: None     Source Type: Journal    
DOI: 10.4052/tigg.20.187     Document Type: Short Survey

References (41)

1. Casu, B., and Lindahl, U. (2001) Adv. Carbohydr. Chem. Biochem. 57, 159-206
2. Banoub, J., Baullanger, P., and Lafont, D. (1992) Chem. Rev. 92, 1167-1195
3. Paulsen, H., Kalar, C., and Stenzel, W. (1978) Chem. Ber. 111, 2358-2369
4. Lemieux, R. U., and Ratcliffe, R. M. (1979) Can. J. Chem. 57, 1244-1251
5. Vasella, A., Witzig, C., Chiara, J. L., and Martin-Lomas, M. (1991) Helv. Chem. Acta. 74, 2073-2077
6. Alper, P. B., Hung, S-C., and Wong, C-H. (1996) Tetrahedron Lett. 37, 6029-6032
7. Pozsgay, V. J. Carbohydr. Chem. (2001), 20, 659-665
8. Demchenko, A. V. Stauchi, T. and Boons, G-J. (1997) Synlett, 818-820
9. Benakli, K., Zha, C., and Kerns, R. J. (2001) J. Am. Chem. Soc. 123, 9461-9462
10. Boysen, M., Gemma, E., Lahmann, M. and Oscarson, S. (2005) Chem. Commun. 3044-3046
11. Kerns, R. J., Zha, C., Benakli, K., and Liang, Y-Z. (2003) Tetrahedron Lett. 44, 8069-8072
12. Wei, P., and Kerns, R. J. (2005) J. Org. Chem. 70, 4195-4198
13. Wei, P., and Kerns, R. J. (2005) Tetrahedron Lett. 46, 6901-6905
14. Manabe, S., Ishii, K., and Ito, Y. (2006) J. Am. Chem. Soc. 128, 10666-10667
15. For the utility of chloroacetyl group in rapid oligosaccharide synthesis; a) Ando, H., Manabe, S., Nakahara, Y., and Ito, Y. (2001) J. Am. Chem. Soc. 123, 3848-3849
16. b) Ando, H., Manabe, S., Nakahara, Y., and Ito, Y. (2001) Angew. Chem. Int. Ed. 40, 4725-4728
17. c) Manabe, S., and Ito, Y. (2002) J. Am. Chem. Soc. 125, 12638-12639
18. d) Hanashima, S., Manabe, S., and Ito, Y. (2005) Angew.Chem. Int. Ed. 44, 4218-4224
19. Demchenko, A. V., Stauchi, T., and Boons, G-J. (1997) Synlett, 818-820
20. Crich, D., and Sun, S. (1998) J. Am. Chem. Soc. 120, 435-436
21. Durón, S. G., Polat, T., and Wong, C-H. (2004) Org. Lett. 6, 839-841
22. Petitou, M., and van Boeckel, C. A. A. (2004) Angew. Chem. Int. Ed. 43, 3118-3133
23. a) Douglas, N. L.; Ley, S. V., Lucking, U., and Warriner, S. L. (1998) J. Chem. Soc. Perkin Trans 1, 51-66;
24. b) Koeller, K. M., and Wong, C-H. (2000) Chem. Rev. 100, 4465-4493;
25. c) Pamela, S., and Wong, C-H. (2001) Science, 291, 2344-2350
26. d) Tanaka, H., Yamada, H., and Takahashi, T. (2007) Trends Glycosci. Glycotech. 19, 181-193
27. Warren, J. R., and Marshall, B. J. (1983) Lancet, 321, 1273-1275
28. Marshall, B. J., Armstrong, J. A., McGechie, D. B., and Glancy, R. J. (1985) Med. J. Aust. 142, 436-439
29. Japanese scientists also found the relationships between bacteria and stomach inflammation about 90 years ago; Kasai, K., and Kobayashi, R. (1919) J. Parasitol. 6, 1-10
30. Kawakubo, M., Ito, Y., Okimura, Y., Kobayashi, M., Sakura, K., Kasama, S., Fukuda, M. N., Fukuda, M., Katsuyama, T., and Nakayama, J. (2004) Science, 305, 1003-1007
31. Lebrun, A-H., Christian, W., Hildebrand, J., Chunin, Y., Zähringer, U., Lindner, B., Meyer, T. F., Heinz, E., and Warnecke, D. (2006) J. Biol. Chem. 281, 27765-27772
32. Lee, H., Kobayashi, M., Wang, P., Nakayama, J., Seeberger, P. H., and Fukuda, M. (2006) Biochem. Biophys. Res. Commun. 349, 1235-1241
33. Wunger, C., Churin, Y., Winau, F., Warnecke, D., Vieth, M., Lindner, B., Zähringer, U., Mollenkopf, H.-J., Heinz, E., and Meyer, T. F. (2006) Nature Medicine, 12, 1030-1038
34. Nakayama, J., Yeh, J-C., Misra, A. K., Ito, S., Katsuyama, T., and Fukuda, M. (1999) Proc. Natl. Acad. Sci. USA, 96, 8991-8996
35. Nakayama, J., Kawakubo, M., Fukuda, M., and Katsuyama, T. PCT Patent Appl. WO 2005/081904
36. Manabe, S., Ishii, K., and Ito, Y. (2007) J. Org. Chem. 72, 6107-6115
37. Li, Z., and Gildersleeve, J. C. (2006) J. Am. Chem. Soc. 128, 11612-11619
38. Wang, P., Lee, H., Fukuda, M. and Seeberger, P. H. (2007) Chem. Commun. 1963-1965
39. Ito, Y., and Manabe, S. (2002) Chem. Eur. J. 8, 3076-3084
40. "Comprehensive Glycoscience", Ito, Y., and Manabe, S. Elsevier, I 335-378
41. Tanaka, H. Nishiura, Y. and Takahashi, T (2006) J. Am. Chem. Soc. 128, 7124-7125.