A Practical and Enantioselective Synthesis of Glycosphingolipids and Related Compounds. Total Synthesis of Globotriaosylceramide (Gb3)

Journal of the American Chemical Society

Volumn 110, Issue 23, 1988, Pages 7910-7912

  Nicolaou, K C ^a   Caulfield, T ^a   Kataoka, H ^b   Kumazawa, T ^c  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b ZEON CORPORATION   (Japan)

^c Kvowa Hakko Koevo Co ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLOBOTRIAOSYLCERAMIDE; GLYCOSPHINGOLIPID;

DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; PRELIMINARY COMMUNICATION;

EID: 0023768505     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00231a071     Document Type: Article

References (37)

1. Hakomori, S. “Glycolipids of Animal Cell Membranes”, Int. Rev. Sci., Org. Chem. Ser. Two 1976, 223.
2. Sharon, N.; Lis, H.; Chem. Eng. News 1981, 59, 21.
3. Li, Y.-T.; Li, S.-C.; Adv. Carbohydr. Chem. Biochem. 1982, 40, 235.
4. Sharon, N.; Trends Biochem. Sci., 9, 198.
5. Hakomori, S.; Sci. Am. 1986, 154, 44.
6. Marcus, D. M.; Class, L. Science (Washington, D.C.) 1969, 164, 553.
7. Hakomori, S.; Stellner, K.; Watanabe, K.; Biochem. Biophys. Res. Commun. 1972, 49, 1061.
8. Marcus, D. M.; Naiki, M.; Kundu, S.K.; Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 3263.
9. Hakomori, S.; Watanabe, K.; Laine, R.A.; Pure Appl. Chem. 1977, 49, 1215.
10. Niemann, H.; Watanabe, K.; Hakomori, S.; Childs, R. A.; Feizi, T.; Biochem. Biophys. Res. Commun. 1978, 81, 1286.
11. Watanabe, K.; Hakomori, S.; Childs, R. A.; Feizi, T.; J. Biol. Chem. 1979, 254, 3221.
12. Feizi, T.; Childs, R. A.; Watanabe, K.; Hakomori, S.; J. Exp. Med. 1979, 149, 975.
13. Hakomori, S.; Andrews, H. D. Biochem. Biophys. Acta 1970, 202, 225.
14. Watanabe, K.; Matsubara, T.; Hakomori, S.; J. Biol. Chem. 1976, 251, 2385.
15. Magnari, J. L.; Nilsson, B.; Brockhous, M.; Zopf, D.; Ginsburg, V.; J. Biol. Chem. 1982, 257, 14365.
16. Hakomori, S.; Kannagi, R.; J. Natl. Cancer. Int. 1983, 71, 231.
17. Hakomori, D.; Nudelman, E.; Levery, S. B.; Patterson, C. M.; Biol. Biophys. Res. Commun. 1983, 113, 791.
18. Kannagi, R.; Levery, S. B.; Hakomori, S.; J. Biol. Chem. 1984, 259, 844.
19. Review: (a) Hakomori, S. Ann. Rev. Biochem. 1981, 50, 733.
20. Hakomori, S.; Ann. Rev. Immunol. 1984, 2, 103.
21. Hakomori, S.; Ann. Rev. Immunol. 1984, 2, 103
22. Hakomori, S.; Siddiqui, B.; Li, Y.-T.; Li, S.-C.; Hellerquist, C. G. J. Biol. Chem. 1971, 246, 2271.
23. Hakomori, S.; Andrews, H. D.; Biochem. Biophys. Acta 1970, 202, 225.
24. McKibbin, J. M.; Spencer, W. A.; Smith, E. L.; Mansson, J.-E.; Karlsson, D.-A.; Samuelsson, B. E.; Li, Y.-T.; Li, S.-C.; J. Biol. Chem. 1982, 257, 755.
25. Hakomori, S.; Patterson, C. M.; Nudelman, E.; Sekuguchi, K.; J. Biol. Chem. 1983, 258, 11819.
26. Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1988, 29, 239.
27. Findeis, M. A.; Whitesides, G. M.; J. Org. Chem. 1987, 52, 2838.
28. Julina, R.; Herzig, T; Bernet, B.; Vasella, A.; Helv. Chim. Acta 1986, 69, 368.
29. Schmidt, R. R.; Zimmermann, P.; Tetrahedron Lett. 1986, 27, 481.
30. Roush, W. R.; Adam, M. A.; J. Org. Chem. 1985, 50, 3752.
31. Boyley, H.; Staudring, D. N.; Knowles, J. R. Tetrahedron Lett. 1978, 39, 3633.
32. For details of synthesis, see Supplementary Material. For isolation and biological activity see, for example: Rostami, A.; Sobue, G.; Lisak, R. P.; Pleasure, D. E. Brain Res. 1987, 425, 205.
33. For details of synthesis, see Supplementary Material. For natural occurrence and biological role of this glycosphingolipid see, for example: Symington, F. W.; Murray, W. A.; Bearman, S. A.; Hakomori, S. J. Biol. Chem. 1987, 262, 11356.
34. 3 (8) based on chemical, enzymatic, and spectroscopic means, see: Hakomori, S.; Siddiqui, B.; Li, Y.-T.; Li, S.-C.; Hellerquist, C. G. J. Biol. Chem. 1971, 246, 2271.
35. 3, 8) is an important member of the glycosphingolipid class of marker molecules being highly expressed in most Burkitt lymphoma cell lines, see: Wiels, J.; Holmes, E. H.; Cochran, N.; Tursz, T.; Hakomori, S. J. Biol. Chem. 1984, 259, 14783.
36. 4, (ii) exposure to NaOMe-MeOH, (iii) benzylation with NaH-benzyl bromide, and (iv) fluoride formation with NBS-HF.pyr. Compound 10 was prepared from lactose octaacetate in ca. 70% overall yield by steps (i) and (ii) above. For more details of these and the coupling procedures, see: ref 9a. See, also: Mukaiyama, T.; Murai, Y.; Shoda, S. Tetrahedron Lett. 1981, 22, 431.
37. 3 thus providing an unambiguous proof of the structural identify of this glycosphingolipid.