Synthesis and biological evaluation of aza-C-disaccharides: (1→6), (1→4), and (1→1) linked sugar mimics

Journal of the American Chemical Society

Volumn 119, Issue 21, 1997, Pages 4856-4865

  Johns, Brian A ^a   Pan, Y T ^b   Elbein, Alan D ^b   Johnson, Carl R ^a  

^a WAYNE STATE UNIVERSITY   (United States)

^b UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; GLYCOSIDASE; GLYCOSYLTRANSFERASE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; ENZYME ACTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030952760     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9642929     Document Type: Article

References (55)

1. (a) Fleet, G. W. J.; Karpus, A.; Dwek, R. A.; Fellows L. E.; Tyms, A. S.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Son, J. C.; Wilson, F. X.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W. FEBS Lett. 1988, 237, 128.
2. (b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
3. (c) Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497.
4. (a) Jensen, J. L.; Tsuang, S. C.; Uslan, A. H. J. Org. Chem. 1986, 51, 816.
5. (b) Liu, P. S. J. Org. Chem. 1987, 52, 4717.
6. (c) Cogoli, A.; Semenza, G. J. Biol. Chem. 1975, 250, 7802.
7. (d) Sinnot, M. L. Chem. Rev. 1990, 90, 1171.
8. (a) Sunkara, P. S.; Bowlin, T. L.; Liu, P. S.; Sjoerdsma A. Biochem. Biophys. Res. Commun. 1987, 148, 206.
9. (b) Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 330, 74.
10. (c) Walker, B. D.; Kowalski, M.; Goh, W. C.; Kozarsky, K.; Krieger, M.; Rosen, C.; Rohrschneider, L.; Haseltine, W. A.; Sodroski, J. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 8120.
11. (d) Karpas, A.; Fleet, G. W. J.; Dwek, R. A.; Petursson, S.; Namgoong, S. K.; Ramsden, N. G.; Jacob, G. S.; Rademacher, T. W. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 9229.
12. (a) Humphries, M. J.; Matsumoto, K.; White, S. L.; Olden, K. Cancer Res. 1986, 46, 5215.
13. (b) Spearman, M. A.; Jamieson, J. C.; Wright, J. A. Exp. Cell Res. 1987, 168, 116.
14. (a) Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. D.; Wingender, W. Angew. Chem., Int. Ed. Engl. 1981, 20, 744.
15. (b) Horii, S.; Fukase, H.; Matsuo, T.; Kameda, Y.; Asano, N.; Matsui, K. J. Med. Chem. 1986, 29, 1038.
16. (c) Anzeveno, P. B.; Creemer, L. J.; Daniel, J. K.; King, C.-H. R.; Liu, P. S. J. Org. Chem. 1989, 54, 2539.
17. (a) Johnson, C. R.; Golebiowski, A.; Sundram, H.; Miller, M. W.; Dwaihy, R. L. Tetrahedron Lett. 1995, 36, 653.
18. (b) For a recent example of an azasugar thioglycoside, see: Suzuki, K.; Hashimoto, H. Tetrahedron Lett. 1994, 35, 4119.
19. For detailed discussions and data on the topic of C-vs O-glycoside similarities and differences, see: (a) Duda, C. A.; Stevens, E. S. J. Am. Chem. Soc. 1993, 115, 8487. (b) Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88. (c) Espinosa, J.-F.; Cañada, J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
20. For detailed discussions and data on the topic of C-vs O-glycoside similarities and differences, see: (a) Duda, C. A.; Stevens, E. S. J. Am. Chem. Soc. 1993, 115, 8487. (b) Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88. (c) Espinosa, J.-F.; Cañada, J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
21. For detailed discussions and data on the topic of C-vs O-glycoside similarities and differences, see: (a) Duda, C. A.; Stevens, E. S. J. Am. Chem. Soc. 1993, 115, 8487. (b) Wei, A.; Kishi, Y. J. Org. Chem. 1994, 59, 88. (c) Espinosa, J.-F.; Cañada, J.; Asensio, J. L.; Martín-Pastor, M.; Dietrich, H.; Martín-Lomas, M.; Schmidt, R. R.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1996, 118, 10862.
22. (a) Kite, G. C.; Fellows, L. E.; Fleet, G. W. J.; Liu, P. S.; Schofield, A. M.; Smith, N. G. Tetrahedron Lett. 1988, 32, 6483.
23. (b) Aoyagi, S.; Fujimaki, S.; Kibayashi, C. J. Chem. Soc., Chem. Commun. 1990, 1457.
24. (c) Bruce, I.; Fleet, G. W. J.; di Bello, I. C.; Winchester, B. Tetrahedron 1992, 48, 10191.
25. (d) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
26. (e) Holt, K. E.; Leeper, F. J.; Handa, S. J. Chem. Soc., Perkin Trans. 1 1994, 231.
27. (f) Henderson, I.; Laslo, K.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 359.
28. (g) Martin, O. R.; Saavedra, O. M. Tetrahedron Lett. 1995, 36, 799.
29. (h) Martin, O. R.; Xie, F.; Liu, L. Tetrahedron Lett. 1995, 36, 4027.
30. (i) Wong, C.-H.; Provencher, L.; Porco, J. A., Jr.; Jung, S.-H.; Wang, Y.-F.; Chen, L.; Wang, R.; Steensma, D. H. J. Org. Chem. 1995, 60, 1492.
31. (a) Johnson, C. R.; Miller, M. W.; Golebiowski, A.; Sundram, H.; Ksebati, M. B. Tetrahedron Lett. 1994, 35, 8991.
32. (a) Baudat, A.; Vogel, P. Tetrahedron Lett. 1996, 37, 483.
33. (b) Martin, O. R.; Liu, L.; Yang, F. Tetrahedron Lett. 1996, 37, 1991.
34. (c) Frérot, E.; Marquis, C.; Vogel, P. Tetrahedron Lett. 1996, 37, 2023.
35. (d) Saavedra, O. M.; Martin, O. R. J. Org. Chem. 1996, 61, 6987.
36. The diol derived from bromobenzene is now prepared in crystalline form on a multikilogram scale by Genecor International, Inc., Rochester, NY.
37. (a) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
38. (b) Suzuki, A. Pure Appl. Chem. 1991, 63, 419.
39. (c) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
40. Hudlicky, T.; Rulin, F.; Tsunoda, T.; Luna, H.; Anderson, C.; Price, J. D. Isr. J. Chem. 1991, 31, 229.
41. Bajwa, J. S.; Anderson, R. C. Tetrahedron Lett. 1991, 32, 3021.
42. A similar protocol has been demonstrated by Hudlicky using the corresponding vinyl chloride. Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
43. Khan, S. H.; Jain, R. K.; Matta, K. L. Carbohydr. Res. 1990, 207, 57.
44. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975.
45. Yoshimura, J.; Sato, K.-i.; Hashimoto, H. Chem. Lett. 1977, 1327.
46. (a) Petasis, N. A.; Bzowej, E. I. J. Am. Chem. Soc. 1990, 112, 6392.
47. (b) Csuk, R.; Glänzer, B. I. Tetrahedron 1991, 47, 1655.
48. (a) Daly, S. M.; Armstrong, R. W. Tetrahedron Lett. 1989, 30, 5713.
49. (b) Preuss, R.; Jung, K.-H.; Schmidt, R. R. Liebigs Ann. Chem. 1992, 377.
50. Rajanbabu, T. V.; Reddy, G. S. J. Org Chem. 1986, 51, 5458.
51. Tropea, J. E.; Molyneux, R. J.; Kaushal, G. P.; Pan, Y. T.; Mitchell, M.; Elbein, A. D. Biochemistry 1989, 28, 2027.
52. (a) Fleet, G. W. J.; Namgoong, S. K.; Barker, C.; Baines, S.; Jacob, G. S.; Winchester, B. Tetrahedron Lett. 1989, 30, 4439.
53. (b) Winchester, B.; Barker, C.; Baines, S.; Jacob, G. S.; Namgoong, S. K.; Fleet, G. Biochem. J. 1990, 265, 277.
54. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals; Pergamon: Oxford, 1989.
55. Soderquist, J. A.; Negron, A. Org. Synth. 1991, 70, 169.