1-Aza Sugars, Apparent Transition State Analogues of Equatorial Glycoside Formation/Cleavage

Accounts of Chemical Research

Volumn 31, Issue 1, 1998, Pages 1-8

  Bols, Mikael ^a,b,c,d,e  

^a AARHUS UNIVERSITY   (Denmark)

^b TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

^c QUEEN S UNIVERSITY   (Canada)

^d LEO PHARMA A S   (Denmark)

^e Professor Gilbert Stork's Group ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010394309     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar970058r     Document Type: Article

References (60)

1. Pauling, L. Am. Sci. 1948, 36, 51.
2. (a) Janda, K. D.; Shevlin, C. G.; Lo, C.-H. Comprehensive Supramolecular Chemistry, Murakami, Y., Ed.; Pergamon: Oxford, U.K., 1996; Vol. 4, pp 43-72.
3. (b) Lavey, B. J.; Janda, K. D. Antibody Expression and Engineering; Wang, H.; Imanaka, T., Eds.; Washington, DC, 1995; Chapter 10.
4. (c) Lerner, R. A.; Benkovic, S. J.; Schultz, P. G. Science 1991, 252, 659-67.
5. (d) Hilhorst, R. Anal. Chim. Acta 1993, 279, 129-134.
6. (e) Schultz, P. G.; Lerner, R. A. Acc. Chem. Res. 1993, 26, 391-395.
7. (f) Schultz, P. G.; Lerner, R. A. Science 1995, 269, 1835-1842.
8. (g) Partridge, L. J. Biochem. Soc. Trans. 1993, 21, 1096-1098.
9. (h) Posner, B.; Smiley, J.; Lee, I.; Benkovic, S. TIBS 1994, 19, 145-150.
10. (a) Lehmann, J.; Rob, B. Tetrahedron: Asymmetry 1994, 5, 2255-2260.
11. (b) Cottaz, S.; Brimacombe, J. S.; Ferguson, M. A. J. Carbohydr. Res. 1993, 247, 341-345.
12. (c) Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682-11690.
13. (d) Ermert, P.; Vasella, A.; Weber, A.; Rupitz, K.; Withers, S. G. Carbohydr. Res. 1993, 250, 113-128.
14. (e) Martin, O. R.; Saavedra O. M. Tetrahedron Lett. 1995, 36, 799-802.
15. (f) Siriwardena, A. H.; Chiaroni, A.; Riche, C.; El-Daher, S.; Winchester, B.; Grierson, D. S. J. Chem. Soc., Chem. Commun. 1992, 1531-1533.
16. (g) Chan, A. W.-Y.; Ganem, B. Tetrahedron Lett. 1995, 36, 811-814.
17. (h) Schmidt, R. R.; Dietrich, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1328-1329.
18. (i) Washiyama, S.; Kamiya, A.; Esaki, S.; Tanaka, A.; Sugiyama, N.; Kamiya, S. Biosci. Biotechnol. Biochem. 1993, 57, 847-849.
19. (h) Ganem, B. Acc. Chem. Res. 1996, 29, 340-347.
20. Gruters, R. A.; Neefjes, J. J.; Tersmette, M.; de Goede, R. E. Y.; Tulp, A.; Huisman, H. G.; Miedema, F.; Ploegh, H. L. Nature 1987, 320, 74-77.
21. (a) Robinson, K. M.; Begovic, M. E.; Rhinehart, B. L. Heineke, E. W.; Ducep, J.-B.; Kastner, P. R.; Marshall, F. N.; Danzin, C. Diabetes 1991, 40, 825-830.
22. (b) Junge, B.; Heiker, F. -R.; Kurz, J.; Müller, L.; Schmidt, D. D.; Wünsche, C. Carbohydr. Res. 1984, 128, 239-268.
23. (c) Blériot, Y.; Smelt, K. H.; Cadefau, J.; Bollen, M.; Stalmans, W.; Biggadike, K.; Johnson, L. N.; Oikonomakos, N. G.; Lane, A. L.; Crook, S.; Watkin, D. J.; Fleet, G. W. J. Tetrahedron Lett. 1996, 37, 7155-7158.
24. McPhail, D. R.; Lee, J. R.; Fraser-Reid, B. J. Am. Chem. Soc. 1992, 114, 1905-1906.
25. (a) Fleet, G. W. J. Tetrahedron 1985, 26, 5073-5076.
26. (b) Post, C. B.; Karplus, M. J. Am. Chem. Soc. 1986, 108, 1317-1319.
27. Franck, R. W. Bioorg. Chem. 1992, 20, 77-88.
28. (a) McCarter, J. D.; Withers, S. G. J. Am. Chem. Soc. 1996, 118, 241-242.
29. (b) Sinnott, M. L. Chem. Rev. 1990, 90, 1171-1202.
30. Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319-384.
31. Fleet, G. W.; Winchester, B. Glycobiology 1992, 2, 199-210.
32. Ishida, N.; Kumagai, K.; Niida, T.; Tsuruoka, T.; Yumate, H. J. Antibiot. 1967, 20, 66-71.
33. (a) Fellows, L. New Sci. 1989 26 (Aug 26) 45-48.
34. (b) Fellows, L. Chem. Br. 1987 (Sept) 842-844.
35. Truscheit, E.; Frommer, W.; Junge, B.; Müller, L.; Schmidt, D. Angew. Chem. 1981, 93, 738-755.
36. Reymond, J.-L.; Janda, K. D.; Lerner, R. A. Angew. Chem., Int. Ed. Engl. 1991, 30, 1711-3.
37. Bols, M. Carbohydrate Building Blocks; John Wiley Science Publishers: New York, 1995.
38. Koyama, M.; Aijima, T.; Sakamura, S. Agric. Biol. Chem. 1974, 38, 1467-1469.
39. Jespersen, T. M.; Dong, W.; Skrydstrup, T.; Sierks, M. R.; Lundt, I.; Bols, M. Angew. Chem. 1994, 33, 1778-1779.
40. Trnka, T.; Cerny, M. Collect. Czech. Chem. Commun. 1971, 36, 2216-2225.
41. Inghardt, T.; Frejd, T. Synthesis 1990, 285-291.
42. Jespersen, T. M.; Bols, M.; Sierks, M. R.; Skrydstrup, T. Tetrahedron 1994, 50, 13449-13460.
43. Dong, W.; Jespersen, T. M.; Bols, M.; Skrydstrup, T.; Sierks, M. R. Biochemistry 1996, 35, 2788-2795.
44. Hansen, A.; Tagmose, T. M.; Bols, M. J. Chem. Soc., Chem. Commun. 1996, 2649-2650.
45. McCaig, A. E.; Chomier, B.; Wightman, R. H. J. Carbohydr. Chem. 1994, 13, 397-407.
46. Igarashi, Y.; Ichikawa, M.; Ichikawa, Y. Bioorg. Med. Chem. Lett. 1996 6 553-558.
47. Hansen, A.; Tagmose, T. M.; Bols, M Tetrahedron 1997, 697-706.
48. Florent, J.-C.; Ughetto-Monfrin, J.; Monneret, C. J. Org. Chem. 1987, 52, 1051-1056.
49. Ho, P. T. Can. J. Chem. 1979, 57, 381-383.
50. Bols, M.; Persson, M. P.; Butt, W. M.; Jørgensen, M.; Christensen, P.; Hansen, L. T. Tetrahedron Lett. 1996, 37, 2097-2100.
51. Ichikawa, M.; Ichikawa, Y.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 1767-70.
52. Ichikawa, Y.; Igarashi, Y. Tetrahedron Lett. 1995, 36, 4585-4586.
53. Ichikawa, M.; Ichikawa, Y. Bioorg. Med. Chem. 1995, 3, 161-165.
54. Igarashi, Y.; Ichikawa, M.; Ichikawa, Y. Tetrahedron Lett. 1996, 37, 2707-2708.
55. Bols, M.; Hazell, R.; Thomsen, I. Chem. Eur. J. 1997, 3, 940-947.
56. For another example of a hydroxyhexahydropyridazine see Paulsen, H.; Steinert, G. Chem. Ber. 1970, 103, 1834-1845.
57. Dale, M. P.; Ensley, H. E.; Kern, K.; Sastry, K. A. R.; Byers, L. D. Biochemistry 1985, 24, 3530-3539.
58. Thomsen, I.; Ernholt, B. V.; Bols, M. Tetrahedron 1997, 53, 2357-2364.
59. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, U.K., 1983; pp 31-35.
60. Strynadka, N. C. J.; James, M. N. G. J. Mol. Biol. 1991, 220, 401-424.