Synthesis of C-5 analogs of N-acetylneuraminic acid via indium-mediated allylation of N-substituted 2-amino-2-deoxymannoses

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8739-8745

  Choi, Seok Ki ^a   Lee, Shelly ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

N ACETYLNEURAMINIC ACID DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030457106     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9614856     Document Type: Article

References (74)

1. The IUPAC name for neuraminic acid is 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonic acid.
2. For review, see: (a) Horowitz, M. I.; Pigman, W. The Glycoconjugates; Academic Press: New York, 1977-1985; Vols. 1-4. (b) Karlsson, K.-A. Curr. Opin. Struct. Biol. 1995, 5, 622. (c) Wiegandt, H. In Glycolipids; Wiegandt, H., Ed.; Elsevier: New York, 1985; Vol. 10, p 199. (d) Varki, A. Glycobiology 1993, 3, 97.
3. For review, see: (a) Horowitz, M. I.; Pigman, W. The Glycoconjugates; Academic Press: New York, 1977-1985; Vols. 1-4. (b) Karlsson, K.-A. Curr. Opin. Struct. Biol. 1995, 5, 622. (c) Wiegandt, H. In Glycolipids; Wiegandt, H., Ed.; Elsevier: New York, 1985; Vol. 10, p 199. (d) Varki, A. Glycobiology 1993, 3, 97.
4. For review, see: (a) Horowitz, M. I.; Pigman, W. The Glycoconjugates; Academic Press: New York, 1977-1985; Vols. 1-4. (b) Karlsson, K.-A. Curr. Opin. Struct. Biol. 1995, 5, 622. (c) Wiegandt, H. In Glycolipids; Wiegandt, H., Ed.; Elsevier: New York, 1985; Vol. 10, p 199. (d) Varki, A. Glycobiology 1993, 3, 97.
5. For review, see: (a) Horowitz, M. I.; Pigman, W. The Glycoconjugates; Academic Press: New York, 1977-1985; Vols. 1-4. (b) Karlsson, K.-A. Curr. Opin. Struct. Biol. 1995, 5, 622. (c) Wiegandt, H. In Glycolipids; Wiegandt, H., Ed.; Elsevier: New York, 1985; Vol. 10, p 199. (d) Varki, A. Glycobiology 1993, 3, 97.
6. (a) Corfield, A. P.; Schauer, R. In Sialic Acids, Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer Verlag: New York, 1982; Vol. 10, pp 5-39.
7. (b) Vliegenthart, J. F. G.; Kamerling, J. P. In Sialic Acids, Chemistry, Metabolism and Function; Schauer, R., Ed.; Springer Verlag: New York, 1982; Vol. 10, pp 59-76.
8. (c) Roy, R.; Laferrière, C. A.; Pon, R. A.; Gamian, A. In Methods in Enzymology (Neoglycoconjugates. Part B. Biomedical Applications); Lee, Y. C., Lee, R. T., Eds.; Academic Press, Inc: San Diego, 1994; Vol. 247, pp 351-361.
9. (a) Magnani, J. L.; Nilsson, B.; Brockhaus, M.; Zopf, D.; Steplewski, Z.; Koprowski, H.; Ginsburg, V. Cancer Res. 1983, 43, 5489.
10. (b) Danishefsky, S. J.; Koseki, K.; Griffith, D. A.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331.
11. Nakayama, J.; Fukuda, M. N.; Fredette, B.; Ranscht, B.; Fukuda, M. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 7031.
12. (a) Rossen, S. D.; Bertozzi, C. R. Curr. Opin. Cell Biol. 1994, 6, 663.
13. (b) Lasky, L. A. Annu. Rev. Physiol. 1995, 57, 827.
14. Kelm, S.; Pelz, A.; Schauer, R.; Filbin, M. T.; Tang, S.; Bellard, M.-E. d.; Schnaar, R. L.; Mahoney, J. A.; Hartnell, A.; Bradfield, P.; Crocker, P. R. Curr. Biol. 1994, 4, 965.
15. Livingston, B. D.; Jacobs, J. L.; Glick, M. C.; Troy, F. A. J. Biol. Chem. 1988, 263, 9443.
16. Edelman, G. M. Annu. Rev. Biochem. 1985, 54, 135.
17. Watowich, S. J.; Skehel, J. J.; Wiley, D. C. Structure 1994, 2, 719.
18. Stehle, T.; Yan, Y.; Benjamin, T. L.; Harrison, S. C. Nature 1994, 369, 160.
19. Méndez, E.; Arias, C. F.; López, S. J. Virol. 1993, 67, 5235.
20. Dallocchio, F.; tomasi, M.; Bellini, T. Biochem. Biophys. Res. Commun. 1995, 208, 36.
21. (a) Stein, P. E.; Boodhoo, A.; Armstrong, G. D.; Heerze, L. D.; Cockle, S. A.; Klein, M. H.; Read, R. J. Nature Struct. Biol. 1994, 1, 591.
22. (b) Sim, B. K. L.; Chitnis, C. E.; Wasniowska, K.; Hadley, T. J.; Miller, L. H. Science 1994, 264, 1941.
23. (a) Lanzrein, M.; Schlegel, A.; Kempf, C. Biochem. J. 1994, 302, 313.
24. (b) Paulson, J. C. In The Receptors; Conn, P. M., Ed.; Academic Press: Orlando, 1985; Vol. 2, pp 131-219.
25. (c) Rossmann, M. G. Protein Sci. 1994, 3, 1712.
26. (a) Paulson, J. C.; Rogers, G. N.; Caroll, S. M.; Higa, H. H.; Pritchet, T.; Milks, G.; Sabesan, S. Pure Appl. Chem. 1984, 56, 797.
27. (b) Brossmer, R.; Gross, H. J. In Methods in Enzymology (Neoglycoconjugates. Part B. Biomedical applications); Lee, Y. C., Lee, R. T., Eds.; Academic Press, Inc.: San Diego, 1994; Vol. 247, pp 153-176.
28. (a) Pritchett, T. J.; Brossmer, R.; Rose, U.; Paulson, J. C. Virology 1987, 760, 502.
29. (b) Machytka, D.; Kharitonenkov, I.; Isecke, R.; Hetterich, P.; Brossmer, R.; Klein, R. A.; Klenk, H.-D.; Egge, H. FEBS Lett. 1993, 334, 117.
30. Springer, T. A. Cell 1994, 76, 301.
31. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J. Ø.; Bock, K. J. Am. Chem. Soc. 1994, 116, 1616.
32. (a) Schmid, W.; Avila, L. Z.; Williams, K. W.; Whitesides, G. M. Bioorg. Med. Chem. Lett. 1993, 3, 747.
33. (b) Murakami, M.; Ikeda, K.; Achiwa, K. Carbohydr. Res. 1996, 280, 101.
34. Brossmer, R.; Gross, H. J. In Methods in Enzymology (Neoglycoconjugates. Part B. Biomedical Applications); Lee, Y. C., Lee, R. T., Eds.; Academic Press, Inc.: San Diego, 1994; Vol. 247, pp 177-193.
35. (a) Gross, H. J.; Rose, U.; Krause, J. M.; Paulson, J. C.; Schmid, K.; Feeney, R. E.; Brossmer, R. Biochemistry 1989, 28, 7386.
36. (b) Gross, H. J.; Brossmer, R. Eur. J. Biochem. 1988, 177, 583.
37. Gross, H. J.; Sticher, U.; Brossmer, R. Anal. Biochem. 1990, 186, 127.
38. (a) Horst, G. T. J. v. d.; Mancini, G. M. S.; Brossmer, R.; Rose, U.; Verheijen, F. W. J. Biol. Chem. 1990, 265, 10801.
39. (b) Mirelis, P.; Brossmer, R. Bioorg. Med. Chem. Lett. 1995, 5, 2809.
40. (a) Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1993, 58, 7937.
41. (b) Chan, T.-H.; Lee, M.-C. J. Org. Chem. 1995, 60, 4228.
42. (c) Roy, R.; Laferriere, C. A. Can. J. Chem. 1990, 68, 2045.
43. (d) Paulsen, H. Angew. Chem., Int. Ed. Engl. 1990, 29, 823.
44. (a) For review, see: Gijsen, H. J. M.; Qiao, L.; Fitz, W.; Wong, C.-H. Chem. Rev. 1996, 96, 443.
45. (b) Lin, C.-H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138.
46. (c) Simon, E. S.; Bednarski, M. D.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 110, 7159.
47. (d) Schrell, A.; Whitesides, G. M. Liebigs Ann. Chem. 1990, 1111.
48. (e) Bednarski, M. D.; Waldmann, H. J.; Whitesides, G. M. Tetrahedron Lett. 1986, 27, 5807.
49. (f) Augé, C.; David, S.; Veyrieres, C. G. e. A. Tetrahedron Lett. 1985, 26, 2439.
50. Czarniecki, M. F.; Thornton, E. R. J. Am. Chem. Soc. 1977, 99, 8273.
51. (a) Chao, L. C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253.
52. (b) Petrier, C.; Einhorn, J.; Luche, J. L. Tetrahedron Lett. 1985, 26, 1449.
53. (c) Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
54. (d) Li, C. J.; Chan, T. H. Tetrahedron Lett. 1991, 32, 7017.
55. (e) Raquette, L. A.; Lobben, P. C. J. Am. Chem. Soc. 1996, 118, 1917.
56. (f) Raquette, L. A.; Mitzel, T. M. J. Am. Chem. Soc. 1996, 118, 1931.
57. Araki, S.; Katsumura, N.; Ito, H.; Butsugan, Y. Tetrahedron Lett. 1989, 30, 1581.
58. (a) Schmid, W.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 773, 6674.
59. (b) Kim, E.; Gordon, D. M.; Schmid, W.; Whitesides, G. M. J. Org. Chem. 1993, 58, 5500.
60. (c) Chan, T. H.; Li, C.-J. J. Chem. Soc., Chem. Commun. 1992, 747.
61. (d) Gao, J.; Härter, R.; Gordon, D. M.; Whitesides, G. M. J. Org. Chem. 1994, 59, 3714.
62. Villieras, J.; Rambaud, M. Org. Synth. 1988, 66, 220.
63. Beuchet, P.; Marrec, N. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
64. Schreiner, E.; Zbiral, E.; Kleineidam, R. G.; Schauer, R. Liebigs Ann. Chem. 1991, 129.
65. Sparks, M. A.; Williams, K. W.; Lukacs, C.; Schrell, A.; Priebe, G.; Spaltenstein, A.; Whitesides, G. M. Tetrahedron 1993, 49, 1.
66. (a) Gross, H. J.; Bünsch, A.; Paulson, J. C.; Brossmer, R. Eur. J. Biochem. 1987, 768, 595.
67. (b) Warner, T. G. Biochem. Biophys. Res. Commun. 1987, 148, 1323.
68. (c) Warner, T. G.; Lee, L. A. Carbohydr. Res. 1988, 176, 211.
69. (a) Itzstein, M. v.; Wu, W.-Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C.; Jin, B.; Phan, T. V.; Smythe, M. L.; White, H. F.; Oliver, S. W.; Colman, P. M.; Varghese, J. N.; Ryan, D. M.; Cameron, J. M.; Penn, C. R. Nature 1993, 363, 418.
70. (b) Zbiral, E.; Sehreiner, E.; Christian, R.; Kleineidam, R. G.; Schauer, R. Liebigs Ann. Chem. 1989, 159.
71. (a) Colman, P. M. Protein Sci. 1994, 3, 1687.
72. (b) Air, G. M.; Laver, W. G. Proteins 1989, 6, 341.
73. Itzstein, M. v.; Wu, W.-Y.; Jin, B. Carbohydr. Res. 1994, 259, 301.
74. For review, see: DeNinno, M. P. Synthesis 1991, 583.