Rationally designed syntheses of high-mannose and complex type undecasaccharides

Carbohydrate Research

Volumn 280, Issue 1, 1996, Pages 67-84

  Nakahara, Yuko ^a   Shibayama, Shohei ^a   Nakahara, Yoshiaki ^a   Ogawa, Tomoya ^a,b  

^a INST OF PHYS AND CHEMICAL RESEARCH   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

Author keywords

complex type; glycans, cell surface; glycosylation; undecasaccharide, high mannose

Indexed keywords

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOPROTEIN SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE;

EID: 0030050797     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/0008-6215(95)00262-6     Document Type: Article

References (39)

1. J. Tamura, K. Neumann, and T. Ogawa, Bioorg. Med. Chem. Lett., 5 (1995) 1351-1354.
2. J. Montreuil, Comprehensive Biochemistry, 19 BII (1982) 1-188.
3. (a) T. Ogawa, H. Yamamoto, T. Nukada, T. Kitajima, and M. Sugimoto, Pure Appl. Chem., 56 (1984) 779-795, and references cited therein;
4. (b) T. Ogawa, T. Kitajima, and T. Nukada, Carbohydr. Res., 123 (1983) C5-C7;
5. T. Ogawa and T. Nukada, Carbohydr. Res., 136 (1985) 135-152;
6. K.K. Sadozai, Y. Ito, T. Nukada, and T. Ogawa, Carbohydr. Res., 150 (1986) 91-101;
7. (e) K.K. Sadozai, T. Kitajima, Y. Nakahara, T. Ogawa, and A. Kobata, Carbohydr. Res., 152 (1986) 173-182;
8. (f) T. Ogawa, M, Sugimoto, T. Kitajima, K.K. Sadozai, and T. Nukada, Tetrahedron Lett., 27 (1986) 5739-5742;
9. (g) F. Yamazaki, T. Kitajima, T. Nukada, Y. Ito, and T. Ogawa, Carbohydr. Res., 201 (1990) 15-30;
10. (h) F. Yamazaki, S. Sato, T. Nukada, Y. Ito, and T. Ogawa, Carbohydr. Res., 201 (1990) 31-50; F. Yamazaki, T. Nukada, Y. Ito, S. Sato, and T. Ogawa, Tetrahedron Lett., 30 (1989) 4417-4420;
11. (h) F. Yamazaki, S. Sato, T. Nukada, Y. Ito, and T. Ogawa, Carbohydr. Res., 201 (1990) 31-50; F. Yamazaki, T. Nukada, Y. Ito, S. Sato, and T. Ogawa, Tetrahedron Lett., 30 (1989) 4417-4420;
12. T. Nukada, T. Kitajima, Y. Nakahara, and T. Ogawa, Carbohydr. Res., 228 (1992) 157-170;
13. (j) T. Ogawa, K. Katano, and M. Matsui, Carbohydr. Res., 64 (1978) C3-C9.
14. S. Ito, K. Yamashita, R.G. Spiro, and A. Kobata, J. Biochem., 81 (1977) 1621-1631.
15. H. van Halbeek, L. Dorland, G.A. Veldink, J.F.G. Vliegenthart, G. Strecker, J.-C. Michalski, J. Montreuil, and W.E. Hull, FEBS Lett., 121 (1980) 71-77.
16. T. Mizuochi, T.J. Matthews, M. Kato, J. Hamako, K. Titani, J. Solomon, and T. Feizi, J. Biol, Chem., 265 (1990) 8519-8524.
17. H. Paulsen and O. Lockhoff, Chem. Ber., 114 (1981) 3102-3114.
18. J.J. Oltvoort, C.A.A. van Boeckel, J.H. de Koning, and J.H. van Boom, Synthesis, (1981) 305-308.
19. R. Gigg and C.D. Warren, J. Chem. Soc. C, (1968) 1903-1911.
20. R.R. Schmit, Angew. Chem., Int. Ed. Engl., 25 (1986) 212-235.
21. Y. Endo, K. Yamashita, Y. Tachibana, S. Tojo, and A. Kobata, J. Biochem., 85 (1979) 669-679.
22. H. Paulsen, Angew. Chem., Int. Ed. Engl., 29 (1990) 823-839.
23. J. Arnarp, and J. Lǒnogran, J. Chem., Soc., Perkin Trans, 1, (1981) 2070-2074.
24. C. Unverzagt, Angew. Chem., Int. Ed. Engl., 33 (1994) 1102-1104.
25. (a) O. Kanie, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem., 7 (1988) 501-506; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, and M. Kiso, J. Carbohydr. Chem., 10 (1991) 493-498;
26. (a) O. Kanie, M. Kiso, and A. Hasegawa, J. Carbohydr. Chem., 7 (1988) 501-506; A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, and M. Kiso, J. Carbohydr. Chem., 10 (1991) 493-498;
27. (b) Y. Ito, T. Ogawa, M. Numata, and M. Sugimoto, Carbohydr. Res., 202 (1990) 165-175;
28. T. Kondo, H. Abe, and T. Goto, Chem. Lett., (1988) 1657;
29. A. Marra and P. Sinaÿ, Carbohydr. Res., 195 (1990) 303-308;
30. (e) H. Lönn and K. Steavall, Tetrahedron Lett., 33 (1992) 115-116;
31. (f) K. Kondo, Y. Ichikawa, and C.H. Wong, J. Am. Chem. Soc., 114 (1992) 8748-8750;
32. (g) T.J. Martin and R.R. Schmidt, Tetrahedron Lett., 33 (1992) 6123-6126.
33. R.U. Lemieux, S.Z. Abbas, M.H. Burynska, and R.M. Ratcliffe, Can. J. Chem., 60 (1982) 63-67.
34. (a) P. Koaraduon, D.R. Mootoo, R.E. McDevitt, and B. Fraser-Reid, J. Chem. Soc., Chem. Commun., 1990, 270-272;
35. (b) GJL Vesneman, S.H. van Loeuwen, and J.H. van Boom, Tetrahedron Lett., 31 (1990) 1331-1334;
36. A. Hasegawa, T. Nagahama, H. Ohki, K. Hotta, H. Ishida, and M. Kiso, J. Carbohydr. Chem., 10 (1991) 493-498.
37. K. Okamoto, T. Kondo, and T. Goto, Tetrahedron, 43 (1987) 5919-5928.
38. K. Suzuki, H. Maeta, and T. Matsumoto, Tetrahedron Lett., 30 (1989) 4853-4856.
39. Y. Matsuzaki, Y. Ito, and T. Ogawa, Tetrahedron Lett., 33 (1992) 6343-6346.