Synthetic Studies on Mannostatin A and Its Derivatives: A New Family of Glycoprotein Processing Inhibitors

Journal of the American Chemical Society

Volumn 116, Issue 2, 1994, Pages 562-570

  King, Stephen Bruce ^a   Ganem, Bruce ^a  

^a Department of Molecular Biology and Genetics   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; ALPHA MANNOSIDASE; MANNOSIDASE INHIBITOR; MANNOSTATIN A; MANNOSTATIN A DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME INHIBITION;

EID: 0028349238     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00081a017     Document Type: Article

References (64)

1. Sharon, N.; Lis, H. Science 1989, 246, 227.
2. Springer, T. A. Nature 1990, 346, 425.
3. Stoolman, L. M. Cell 1989, 56, 907.
4. Carbohydrate-Protein Interactions; Clarke, A. E., Wilson, I. A., Eds; Springer-Verlag: Heidelberg, 1988.
5. Elbein, A. D. Annu. Rev. Biochem. 1987, 56, 497.
6. 1-Deoxynojirimycin: Saunier, B.; Kilker, R. P.; Tkacz, J. S.; Quaroni, A.; Herskovics, A. J. Biol. Chem. 1982, 257, 14155.
7. 1-Deoxymannojirimycin: (a) Fuhrmann, U.; Bause, E.; Legler, G.; Ploegh, H. Nature 1984, 307, 755.
8. Elbein, A. D.; Legler, G.; Tlusty, A.; McDowell, W.; Schwartz, R. T. Arch. Biochem. Biophys. 1984, 235, 579.
9. Legler, G.; Julich, E. Carbohydr. Res. 1984, 128, 61.
10. Fellows, L. E.; Bell, E. A.; Lynn, D. G.; Pilciewicz, F.; Miura, I.; Nakanishi, K. J. Chem. Soc, Chem. Commun. 1979, 977.
11. Castanospermine: Pan, Y. T.; Hori, H.; Saul, R.; Sanford, B. A.; Molyneux, R. J.; Elbein, A. D. Biochemistry 1983, 22, 3975.
12. Swainsonine: (a) Tulsiani, D. P. R.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936.
13. Elbein, A. D.; Solf, R.; Dorling, P. R.; Vosbeck, K. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 7393.
14. Current review: Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
15. Aoyagi, T.; Yamamoto, T.; Kojiri, K.; Morishima, H.;Nagai, M.; Hamada, M.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1989, 42, 883.
16. Morishima, H.; Kojiri, K.; Yamamoto, T.; Aoyagi, T.; Nakamura, H.; Iitaka, Y. J. Antibiot. 1989, 42, 1008.
17. Tropea, J. E.; Kaushal, G. P.; Pastuszak, I.; Mitchell, M.; Aoyagi, T.; Molyneux, R. J.; Elbein, A. D. Biochemistry 1990, 29, 10062.
18. Winkler, D. A.; Holan, G. J. Med. Chem. 1989, 32, 2084.
19. Knapp, S.; Dhar, T. G. M. J. Org. Chem. 1991, 56, 4096.
20. Fellows, L. E. New Sci. 1989, 123, 45.
21. Fellows, L. Chem. Br. 1987, 23, 842.
22. Trugan, G.; Rousset, M.; Zweibaum, A. FEBS Lett. 1986, 195, 28.
23. Sazak, V. V.; Ordovas, J. M.; Elbein, A. D.; Berninger, R. W. Biochem. J. 1985, 232, 759.
24. Humphries, M. J.; Matsumoto, K.; White, S. L.; Molyneux, R. J.; Olden, K. Cancer Res. 1988, 48, 1410.
25. Denis, J. W. Cancer Res. 1986, 46, 5131.
26. King, S. B.; Ganem, B. J. Am. Chem. Soc. 1991, 113, 5089.
27. Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1991, 113, 6317.
28. Ogawa, S.; Yuming, Y. J. Chem. Soc, Chem. Commun. 1991, 890.
29. See, inter alia: (a) Danheiser, R. L.; Carini, D. J.; Basak, A. J. Am. Chem. Soc. 1981, 103, 1604.
30. Danheiser, R. L.; Martinez-Davila, C.; Auchus, R. J.; Kadonaga, J. T. J. Am. Chem. Soc. 1981, 103, 2443.
31. Kirby, G. W. Chem. Soc. Rev. 1977, 6, 1.
32. Kirby, G. W.; Nazeer, M. Tetrahedron Lett. 1988, 29, 6173.
33. Miller, A.; Paterson, T. M.; Procter, G. Synlett 1989, 1, 32.
34. Brouillard-Poichet, A.; Defoin, A.; Streith, J. Tetrahedron Lett. 1989, 30, 7061.
35. Miller, A.; Procter, G. Tetrahedron Lett. 1990, 31, 1041, 1043.
36. Martin, S. F.; Hartmann, M.; Josey, J. A. Tetrahedron Lett. 1992, 33, 3583.
37. Kirby, G. W.; Nazeer, M. J. Chem. Soc, Perkin Trans. 1 1993, 1397-1401.
38. Hartke, K.; Zerbe, H.-G. Arch. Pharm. (Weinheim, Ger.) 1982, 315, 406.
39. Cotton, F. A.; Reynolds, L. T. J. Am. Chem. Soc. 1958, 80, 269.
40. VanRheenan, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
41. Henbest, H. B.; Khan, S. A. J. Chem. Soc, Chem. Commun. 1968, 1036.
42. Hauser, F. M.; Ellenberger, S. R.; Clardy, J. C.; Bass, L. S. J. Am. Chem. Soc. 1984, 106, 2458.
43. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
44. Trost, B. M.; Kuo, G.-H.; Benneche, T, J. Am. Chem. Soc. 1988, 110, 621.
45. Poli.G. Tetrahedron Lett. 1989, 50, 7385 and references cited therein.
46. Keck, G. E.; Fleming, S.; Nickell, D.; Weider, P. Synth. Commun. 1979, 9, 281.
47. Kayakiri, H.; Takase, T.; Shibata, T.; Okamoto, M.; Terano, H.; Hashimoto, M.; Tada, T.; Koda, S. J. Org. Chem. 1989, 54, 4015.
48. Ganem, B.; Papandreou, G. J. Am. Chem. Soc. 1991, 113, 8984.
49. Lai, H.-Y.L.; Axelrod, B. Biochem. Biophys. Res. Commun. 1973, 54, 463.
50. Legler, G. Biochim. Biophys. Acta 1978, 524, 94.
51. Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847.
52. Legler, G.; Bause, E. Carbohydr. Res. 1973, 28, 45.
53. Thomas, E. E.; McKelvy, J. F.; Sharon, N. Nature 1969, 222, 485.
54. Klibanov, A. M. CHEMTECH 1986, 16, 354.
55. House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin: Menlo Park, 1972; pp 353. Hudlicky, M. Oxidations in Organic Chemistry; ACS Monograph 186; American Chemical Society: Washington, DC, 1990; pp 222.
56. Sakuda, S.; Isogai, A.; Makita, T.; Matsumoto, S.; Koseki, K.; Kodama, H.; Suzuki, A. Agric. Biol. Chem. 1987, 51, 3251.
57. Sakuda, S.; Isogai, A.; Matsumoto, S.; Suzuki, A.; Koseki, K.; Kodama, H.; Yamada, Y. Agric. Biol. Chem. 1988, 52, 1615.
58. Nakayame, T.; Amachi, T.; Murao, S.; Sakai, T.; Shin, T.; Kenny, P. T. M.; Iwashita, T.; Zagorski, M.; Komura, H.; Nomoto, K. J. Chem. Soc., Chem. Commun. 1991, 919-921.
59. Uchida, C.; Yamagishi, T.; Ogawa, S. Chem. Lett. 1993, 971.
60. Kobayashi, J.;Zeng,C.;Ishibashi, M. J. Chem. Soc, Chem. Commun. 1993, 79-81.
61. Trost, B. M.; Van Vranken, D. L. J. Am. Chem. Soc. 1993, 115, 444.
62. Macauley, J. B.; Fallis, A. G. J. Am. Chem. Soc. 1990, 112, 1136.
63. Ishida, M.; Aoyama, T.; Kato, S. Chem. Lett. 1989, 663.
64. Winstein, S.; Shatavsky, M.; Norton, C.; Woodward, R. B. J. Am. Chem. Soc. 1955, 77, 4183.