8-O-sialylation of neuraminic acid

Journal of the American Chemical Society

Volumn 120, Issue 22, 1998, Pages 5434-5440

  Castro Palomino, Julio C ^a   Tsvetkov, Yury E ^a   Schmidt, Richard R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

NEURAMINIC ACID;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SIALYLATION;

EID: 0032503568     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9740327     Document Type: Article

References (33)

1. Hakomori, S. Annu. Rev. Immunol. 1984, 2, 103-126.
2. Reisfeld, R. A.; Cheresh, D. A. Adv. Immunl. 1987, 40, 323-377.
3. Karlsson, K. A. Annu. Rev. Biochem. 1989, 58, 309-350.
4. Martin, T. J.; Brescello, R.; Toepfer, A.; Schmidt, R. R. Glycoconjugate J. 1993, 10, 16-25 and refs 1-37 and 42-44 therein.
5. Castro-Palomino, J. C.; Ritter, G.; Fortunato, S.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem. 1997, 109, 2081-2085;
6. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001.
7. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kotta, K.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1991, 10, 493-498.
8. Schmidt, R. R. Lecture at Fuji 1990 Symposium, August 1990: partly published in Carbohydrates-Synthetic Methods aid Application in Medicinal Chemistry; Ogura, H., Hasegawa, A., Suami, T., Eds.; Kodanasha: Tokyo, 1990; pp 66-88.
9. Martin, T. J.; Schmidt, R. R. Tetrahedron Lett. 1992, 33, 6123-6126.
10. Schmidt, R. R.; Rücker, E. Tetrahedron Lett. 1980, 21, 1421-1424;
11. Schmidt, R. R.; Michel, J. J. Carbohydr. Chem. 1985, 4, 141-169.
12. Schmidt, R. R.; Behrendt, M. N.; Toepfer, A. Synlett 1990, 694-696.
13. (a) Castro-Palomino, J. C.; Tsvetkov, Y. E.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1997, 38.
14. (b) Tsvetkov, Y. E.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 8583-8586;
15. Carbohydr. Lett. 1996, 2, 149-156.
16. Kanie, O.; Kiso, M.; Nakomma, J.; Hasegawa, A. J. Carbohydr. Chem. 1987, 6, 117-128.
17. Kanie, O.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. Ibid. 1988, 7, 501-506.
18. Okamoto, K.; Kondo, T.; Goto, T. Tetrahedron 1988, 44, 1291-1298.
19. Ito, Y.; Numata, M.; Sugimoto, M.; Ogawa, T. J. Am. Chem. Soc. 1989, 111, 8508-8510.
20. Ercégovic, T.; Magnusson, G. J. Org. Chem. 1995, 60, 3378-3384.
21. Kondo, T.; Tomoo, T.; Abe, H.; Isobe, M.; Goto, T. J. Carbohydr. Chem. 1996, 15, 857-878.
22. (a) Okamoto, K.; Goto, T. Tetrhadeton 1990, 46, 5835-5857 and references therein.
23. (b) Ito, Y.; Ogawa, T. Tetrahedron 1990, 46, 89-96.
24. (c) Martichonik, V.; Whitesides, M. G. J. Am. Chem. Soc. 1996, 118, 8187-8191.
25. (d) Tomoo, T.; Kondo, T.; Abe, H.; Tsukamoto, S.; Isobe, M.; Goto, T. Carbohydr. Res. 1996, 284, 207-222.
26. (e) Kononoy, L.; Ito, Y.; Ogawa, T. Tetrahedron Lett. 1997,38, 1599-1602.
27. (f) Martichonok, V.; Whitesides, M. G. Carbohydr. Res. 1997, 502, 123-129.
28. A thiocarbonyloxy moiety was claimed to support 2-deoxy-β-ribonucleoside formation via a six-membered intermediate; yet, still both anomers were obtained: Mukaiyama, T.; Hirano, N.; Nishida, M.; Uchiro, H. Chem. Lett. 1996, 99-100.
29. For preliminary publication of part of this approach, see ref 10a.
30. Jung, K.-H.; Hoch, M.; Schmidt, R. R. Liebigs Ann. Chem. 1989, 1099-1106.
31. Hori, H.; Nakajima, T.; Nishida, Y.; Ohrui, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317-6320.
32. Van Rheenan, V.; Cha, D. A.; Hartley, W. M. Org. Synth. Collect. 1988, 6, 342.
33. Barton, H. R. D.; McCombie, W. S. J. Chem. Soc., Perkin Trans. 1 1975, 1574-1585.