Synthesis of the pentasaccharide core structure of asparagine-linked glycoprotein oligosaccharides by the glycal assembly method

Enantiomer

Volumn 1, Issue 4-6, 1996, Pages 311-323

  Seeberger, Peter H ^a   Cirillo, Pier F ^a   Hu, Shuanghua ^a   Beebe, Xenia ^a   Bilodeau, Mark T ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

Glycal assembly method; High mannose core structure; n linked glycoproteins; Oligosaccharide synthesis; Thiodonor couplings

Indexed keywords

ASPARAGINE; GLYCOPROTEIN; MANNOSE; MESYLIC ACID DERIVATIVE; POLYSACCHARIDE; THIOL DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID METHYL ESTER;

ARTICLE; CHEMISTRY; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATION; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

ASPARAGINE; CHROMATOGRAPHY, THIN LAYER; GLYCOPROTEINS; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSE; MASS SPECTROMETRY; MESYLATES; OPTICAL ROTATION; POLYSACCHARIDES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; SULFHYDRYL COMPOUNDS;

EID: 0030310221     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Kornfeld, R. and Kornfeld, S. (1976). Ann. Rev. Biochem., 45, 217;
2. Kobata, A. (1993). Acc. Chem. Res., 26, 319;
3. Varki, A. (1993). Glycobiology, 3, 97;
4. Cummings, R. D. In Glycoconjugates: Composition, Structure, and Function; H. J. Allen and E. C. Kisalius, Eds.; Marcel Dekker: New York, 1992; pp 333;
5. Elbein, A. D. (1991). Trends Biotech., 9, 346
6. Dan, A., Ito, Y. and Ogawa, T. (1995). Tetrahedron Lett., 36, 7487;
7. Matsuo, I., Nakahara, Y., Ito, Y., Nukada, T., Nakahara, Y. and Ogawa, T. (1995). Bio. Med. Chem., 3, 1455;
8. Yamazaki, F., Kitajima, T., Nukada, T., Ito, Y. and Ogawa, T. (1990). Carbohydrate Res., 201, 15;
9. Unverzagt, C. (1994). Angew. Chem. Int. Ed. Engl., 33, 1102;
10. Meritt, J. R., Naisang, E. and Fraser-Reid, B. J. (1994). Og. Chem., 59, 4443;
11. Kunz, H. (1987). Angew. Chem. Int. Ed. Engl., 26, 294;
12. Paulsen, H. (1990). Angew. Chem. Int. Ed. Engl., 29, 823.
13. Paulsen, H. and Lockhoff, O. (1981). Chem. Ber., 114, 3102;
14. Paulsen, H., Lebhuhn, R. and Lockhoff, O. (1982). Carbohydr. Res., 103, C7;
15. Garegg, P. J. and Ossowski, P. (1983). Acta Chem. Scand. Ser. B., 37, 249;
16. van Boeckel, C. A. A., Beetz, T. and van Aelst, S. F. (1984). Tetrahedron, 40, 4097;
17. van Boeckel, C. A. A. and Beetz, T. (1985). Recl. Tray. Chim. Pays-Bas, 104, 171;
18. Lichtenthaler, F. W. and Schneider-Adams, T. (1994). J. Org. Chem., 59, 6728;
19. Lichtenthaler, F. W., Schneider-Adams, T. and Immel, S. (1994). J. Org. Chem., 59, 6735;
20. Auge, C., Warren, C. D., Jeanloz, R. W., Kiso, M. and Anderson, L. (1980). Carbohydr. Res., 188, 193;
21. David, S., Malleron, A. and Dini, C. (1989). Carbohydr. Res., 188, 193;
22. Alais, J. and David, S. (1990). Carbohydr. Res., 201, 69;
23. Kunz, H. and Guenther, W. (1988). Angew. Chem. Int. Ed. Engl., 27, 1086.
24. Barresi, F. and Hindsgaul, O. (1994). Can. J. Chem., 72, 1447;
25. Barresi, F. and Hindsgaul, O. (1992). Synlett, 759;
26. Barresi, F. and Hindsgaul, O. J. (1991). J. Am. Chem. Soc., 113, 9376;
27. Stork, G. and Kim, G. (1992). J. Am. Chem. Soc., 114, 1087.
28. Dan, A., Ito, Y. and Ogawa, T. (1995). J. Org. Chem., 60, 4680.
29. Ekborg, G., Lindberg, B. and Lonngren. (1972). J. Acta Chem. Scand., 26, 3287;
30. Kochetkov, N. K., Dvitriev, B. A., Malysheva, N. N., Cherniak, A. Y., Klimov, E. M., Bauramova, N. E. and Torgov, V. I. (1975). Carbohydr. Res., 45, 283;
31. Shaban, M. A. E. and Jeanloz, R. W. (1976). Carbohydr. Res., 52, 103.
32. Liu, K. K.-C. and Danishefsky, S. J. (1994). J. Org. Chem., 59, 1892.
33. Pfitzer, K. E. and Moffatt, J. G. J. (1965). Am. Chem. Soc., 87, 5661.
34. Danishefsky, S. J., Behar, V., Randolph, J. T. and Lloyd, K. O. (1995). J. Am. Chem. Soc. 117, 5701.
35. Griffith, D. A. and Danishefsky, S. J. (1990). J. Am. Chem. Soc., 112, 5811.
36. Omura, K. and Swern, D. (1978). Tetrahedron, 34, 1651.
37. Dess, D. B. and Martin, J. C. (1991). J. Am. Chem. Soc., 113, 7277.
38. Ley, S. V., Norman, J., Griffith, W. P. and Marsden, P. (1994). Synthesis, 639.
39. Amann, A., Ourisson, G. and Luu, B. (1987). Synthesis, 2002.
40. Mc Donald, F. E. and Danishefsky, S. J. (1992). J. Org. Chem., 57, 7001;
41. Roberge, J. Y., Beebe, X. and Danishefsky, S. J. (1995). Science, 269, 202.