Enzymatic/chemical synthesis and biological evaluation of seven-membered iminocyclitols

Journal of the American Chemical Society

Volumn 118, Issue 33, 1996, Pages 7647-7652

  Morís Varas, Francisco ^a   Qian, Xin Hua ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA GALACTOSIDASE; ALPHA GLUCOSIDASE; ALPHA LEVO FUCOSIDASE; ALPHA MANNOSIDASE; AZEPINE DERIVATIVE; GLYCOSIDASE INHIBITOR; N ACETYL BETA GLUCOSAMINIDASE; POLYOL; PROTEINASE;

ANIMAL TISSUE; ANTIVIRAL ACTIVITY; ARTICLE; CATTLE; CONTROLLED STUDY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; KIDNEY; NONHUMAN; PLANT; REACTION ANALYSIS; X RAY ANALYSIS; YEAST;

EID: 0029840739     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960975c     Document Type: Article

References (38)

1. (a) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
2. (b) Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199.
3. (c) Wong, C.-H.; Halcomb, R. L.; Ichikawa, Y.; Kajimoto, T. Angew. Chem., Int. Ed. Engl. 1995, 34, 521
4. (a) Legler, G. Adv. Carbohydr. Chem. Biochem. 1990, 48, 319.
5. (b) Sinnott, M. L. Chem. Rev. 1990, 90, 1171.
6. (c) Kirby, A. J. Adv. Phys. Org, Chem. 1994, 29, 87.
7. (d) Jacob, G. S. Curr. Opin. Struct. Biol. 1995, 5, 605.
8. (a) McCarter, J. D.; Withers, S. G. Curr. Opin. Struct. Biol. 1994, 4, 885.
9. (b) Ganem, B.; Papandreou, G. J. Am. Chem. Soc. 1991, 113, 8984;
10. (c) Papandreou, G.; Tong, M. K.; Ganem, B. J. Am. Chem. Soc. 1993, 115, 11682.
11. (4)(a) Fotsch, C.; Wong, C.-H. Tetrahedron Lett. 1994, 35, 3481.
12. (b) Jeong, J.-H.; Murray, B. W.; Takayama, S.; Wong, C.-H. J. Am. Chem. Soc., 1996, 118, 4227.
13. (a) Paulsen, H.; Todt, K. Chem. Ber 1967, 100, 512.
14. (b) Poitout, L.; Merrer, Y. L.; Depezay, J-C. Tetrahedron Lett. 1994, 35, 3293.
15. (c) Lohray, B. B.: Jayamma, Y.; Chatterjee, M. J. Org. Chem. 1995, 60, 5958.
16. Farr. R. A.; Holland, A. K.; Huber, E. W.; Peet, N. P.; Weintraub, P. M. Tetrahedron 1994, 50, 1033.
17. Bernotas, R. C.; Pezzone, M. A.; Ganem, B. Carbohydr. Res. 1987, 167, 305.
18. Tulsiani, D. R. P.; Harris, T. M.; Touster, O. J. Biol. Chem. 1982, 257, 7936.
19. Fleet, G. W. J.; Shaw, A. N.; Evans, S. V.; Fellows, L. E. J. Chem. Soc., Chem. Commun. 1985, 841.
20. Qian, X.; Morís-Varas, F.; Wong, C.-H. Bioorg. Med. Chem. Lett. 1996, 6, 117.
21. Qian, X.; Morís-Varas, F.; Fitzgerald, M. C.; Wong, C.-H. Bioorg. Med. Chem., in press.
22. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: Oxford, 1994.
23. Fuel prefers (2S,3R)- and Rhal prefers (2A,3R)-aldose as substrate. Glucose isomerase prefers (2R,3S) aldose as substrate. For synthethic work using isomerases see: (a) Fessner, W.-D.; Badía, J.; Eyrisch, O.; Schneider, A.; Sinerius, G. Tetrahedron Lett. 1992, 33, 5231. (b) Alajarín, R.; García-Junceda, E.; Wong, C.-H. J. Org. Chem. 1995, 60, 4294. (c) Wong, C-H.; Alajarín, R.; Morís-Varas, F.; Blanco, O.; Wong, C.-H. J. Org. Chem. 1995, 60, 7360. (d) Page, P.; Blonski, C.; Périé J. Tetrahedron, 1996, 52, 1557.
24. Fuel prefers (2S,3R)- and Rhal prefers (2A,3R)-aldose as substrate. Glucose isomerase prefers (2R,3S) aldose as substrate. For synthethic work using isomerases see: (a) Fessner, W.-D.; Badía, J.; Eyrisch, O.; Schneider, A.; Sinerius, G. Tetrahedron Lett. 1992, 33, 5231. (b) Alajarín, R.; García-Junceda, E.; Wong, C.-H. J. Org. Chem. 1995, 60, 4294. (c) Wong, C-H.; Alajarín, R.; Morís-Varas, F.; Blanco, O.; Wong, C.-H. J. Org. Chem. 1995, 60, 7360. (d) Page, P.; Blonski, C.; Périé J. Tetrahedron, 1996, 52, 1557.
25. Fuel prefers (2S,3R)- and Rhal prefers (2A,3R)-aldose as substrate. Glucose isomerase prefers (2R,3S) aldose as substrate. For synthethic work using isomerases see: (a) Fessner, W.-D.; Badía, J.; Eyrisch, O.; Schneider, A.; Sinerius, G. Tetrahedron Lett. 1992, 33, 5231. (b) Alajarín, R.; García-Junceda, E.; Wong, C.-H. J. Org. Chem. 1995, 60, 4294. (c) Wong, C-H.; Alajarín, R.; Morís-Varas, F.; Blanco, O.; Wong, C.-H. J. Org. Chem. 1995, 60, 7360. (d) Page, P.; Blonski, C.; Périé J. Tetrahedron, 1996, 52, 1557.
26. Fuel prefers (2S,3R)- and Rhal prefers (2A,3R)-aldose as substrate. Glucose isomerase prefers (2R,3S) aldose as substrate. For synthethic work using isomerases see: (a) Fessner, W.-D.; Badía, J.; Eyrisch, O.; Schneider, A.; Sinerius, G. Tetrahedron Lett. 1992, 33, 5231. (b) Alajarín, R.; García-Junceda, E.; Wong, C.-H. J. Org. Chem. 1995, 60, 4294. (c) Wong, C-H.; Alajarín, R.; Morís-Varas, F.; Blanco, O.; Wong, C.-H. J. Org. Chem. 1995, 60, 7360. (d) Page, P.; Blonski, C.; Périé J. Tetrahedron, 1996, 52, 1557.
27. de Raadt, A.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 189.
28. (a) Paulsen, H.; Sangster, I.; Heyns, K. Chem. Ber. 1967, 100, 802.
29. 2 (50 psi) the only product obtained was the aminohexopyranose: (b) Liu, K. C.; Pederson, R. L.; Wong, C. H. J. Chem. Soc., Perkin Trans I 1991, 1991, 2669.
30. von der Osten, C. H.; Barbas, C. F.; Wong, C. H.; Pederson, R. L.; Sinskey, A. J.; Wang, Y. F. J. Am. Chem. Soc. 1989, 111, 3924.
31. Durrwachter, J. R.; Drueckhammer, D. G.; Nozaki, K.; Sweers, H. M.; Wong, C. H. J. Am. Chem. Soc. 1986, 108, 7812.
32. Berger, A.; de Raadt, A.; Gradnig, G.; Grasser, M.; Löw, H.; Stütz, A. E. Tetrahedron Lett. 1992, 33, 7125.
33. Henderson, I.; García-Junceda, E.; Liu, K. K.-C.; Chen, Y.-L.; Shen, G.-J.; Wong, C.-H. Bioorg. Med. Chem. 1994, 2, 837.
34. García-Junceda, E.; Shen, G.-J.; Alajarín, R.; Wong, C.-H. Bioorg. Med. Chem. 1995, 3, 1349.
35. Bergmeyer, H. U. Methods of Enzymatic Analysis, 3rd ed.; Verlag Chemie: Deerfield, FL, 1984; Vol. 2, p 146.
36. Straub, A.; Effenberger, F.; Fischer, P. J. Org. Chem. 1990, 55, 3926.
37. Durrwachter, J. R.; Wong, C. H. J. Org. Chem. 1988, 53, 4175.
38. Cleland, W. W. Methods Enzymol. 1979, 63, 103.