Synthesis of per-glycosylated β-cyclodextrins having enhanced lectin binding affinity

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 522-531

  García López, Juan José ^a   Hernández Mateo, Fernando ^b   Isac García, Joaquín ^b   Kim, Jin Mi ^c   Roy, René ^c   Santoyo González, Francisco ^b   Vargas Berenguel, Antonio ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF ALMERÍA   (Spain)

^c UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; CARBOHYDRATE; CELL SURFACE RECEPTOR; CESIUM; DRUG CARRIER; LECTIN; OLIGOSACCHARIDE; THIOUREA DERIVATIVE; VEGETABLE PROTEIN;

ARTICLE; BINDING AFFINITY; CHEMICAL PROCEDURES; CHEMICAL STRUCTURE; COMPETITIVE INHIBITION; CROSS LINKING; NONHUMAN; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0039003336     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981576y     Document Type: Article

References (59)

1. Varki, A. Glycobiology 1993, 3, 97.
2. Lee, R. T.; Lee, Y. C. In Neoglycoconjugates; Lee, Y. C., Lee, R. T., Eds.; Academic Press: San Diego, 1994; pp 23-50.
3. Lee, Y. C.; Lee, R. T. Acc. Chem. Res. 1995, 28, 321.
4. (a) Roy, R. In Modern Methods in Carbohydrate Synthesis; Khan, S. H., O'Neill, R. A., Eds.; Harwood Academic: Amsterdam, 1996; pp 378-402.
5. (b) Roy, R. Top. Curr. Chem. 1997, 187, 241.
6. (a) Roy, R. Trends Glycosci. Glycotechnol. 1996, 8, 79.
7. (b) Roy, R. In Carbohydrate Chemistry; Boon, G.-J., Ed.; Blackie A & P: London, UK, 1998; pp 243-321.
8. (a) Roy, R. In Carbohydrate: Targets for Drug Design; Witczak, Z. J., Nieforth, K. A., Eds.; Marcel Dekker Inc.: New York, 1997; pp 83-135.
9. (b) Zanini, D.; Roy, R. In Carbohydrate Mimics: Concepts and Methods; Chapleur, Y., Ed.; Verlag Chemie: Weinheim, Germany, 1998; pp 385-415.
10. (a) Roy, R.; Zanini, D.; Meunier, S. J.; Romanoska, A. In Synthetic Oligosaccharides: Indispensable Probes for the Life Sciences; Kovác, P., Ed.; ACS Symposium Series: Washington, DC, 1994; pp 104-119.
11. (b) Zanini, D.; Roy, R. J. Am. Chem. Soc. 1997, 119, 2088.
12. (c) Zanini, D.; Roy, R. J. Org. Chem. 1998, 63, 3486.
13. (a) Roy, R. Polym. News 1996, 21, 226.
14. (b) Roy, R. Curr. Opin. Struct. Biol. 1996, 6, 692.
15. Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Nepogodiev, S. A.; Meijer, E. W.; Peerlings; HWI.; Stoddart, J. F. Chem. Eur. J. 1997, 3, 974.
16. Aoi, K.; Itoh, K.; Okada, M. Macromolecules 1995, 28, 5391.
17. Lindhorst, T. K.; Kieburg, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1953.
18. Zeng, F. W.; Zimmerman, S. C. Chem. Rev. 1997, 97, 1681.
19. Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Jayaraman, N.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1997, 36, 732.
20. Meunier, S. J.; Roy, R. Tetrahedron Lett. 1996, 37, 5469.
21. (a) Marra, A.; Scherrmann, M. C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew. Chem., Int. Ed. Engl. 1995, 33, 2479.
22. (b) Marra, A.; Dondoni, A.; Sansone, F. J. Org. Chem. 1996, 61, 5155.
23. (a) Dondoni, A.; Marra, A.; Scherrmann, M. C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Eur. J. 1997, 3, 1774. Dondoni, A.; Kleban, M.; Marra, A. Tetrahedron Lett. 1997, 38, 7801.
24. (a) Dondoni, A.; Marra, A.; Scherrmann, M. C.; Casnati, A.; Sansone, F.; Ungaro, R. Chem. Eur. J. 1997, 3, 1774. Dondoni, A.; Kleban, M.; Marra, A. Tetrahedron Lett. 1997, 38, 7801.
25. Fujimoto, T.; Shimizu, C.; Hayashida, O.; Aoyama, Y. J. Am. Chem. Soc. 1997, 119, 6676.
26. Dumont, B.; Joly, J. P.; Chapleur, Y.; Marsura, A. Bioorg. Med. Chem. Lett. 1994, 4, 1123.
27. König, B.; Fricke, T.; Wamann, A.; Krallmann-Wenzel, U.; Lindhorst, T. K. Tetrahedron Lett. 1998, 39, 2307.
28. Kingerywood, J. E.; Williams, K. W.; Sigal, G. B.; Whitesides, G. M. J. Am. Chem. Soc. 1992, 114, 7303.
29. (a) Sakai, S.; Sasaki, T. J. Am. Chem. Soc. 1994, 116, 1587.
30. (b) Sakai, S.; Shigemasa, Y.; Sasaki, T. Tetrahedron Lett. 1997, 38, 8145.
31. (c) Roy, R.; Kim, J. M. PMSE 1997, 77, 195.
32. Bender, M. L.; Komiyama, M. Cyclodextrins Chemistry; Springer-Verlag: New York, 1978.
33. Atwood, J. L.; Davies, J. E. D.; MacNicole, D. Inclusion Compounds; Academic Press: London, 1984.
34. Szejtli, J. Cyclodextrins and Their Inclusion Complexes; Academiae Kiado: Budapest, 1982.
35. Szejtli, J. Cyclodextrins Technology; Kluwer Academic Publisher: Boston, 1988.
36. Li, S.; Purdy, W. C. Chem. Rev. 1992, 92, 1457.
37. Szejtli, J. Cyclodextrins; Pergamon: New York, 1996.
38. Duchêne, D. New Trends in Cyclodextrin and Derivatives; Editions de Santé: Paris, 1991.
39. Szejtli, J. Med. Res. Rev. 1994, 14, 353.
40. Cottaz, S.; Driguez, H. Synthesis 1989, 755.
41. Lancelon-Pin, C.; Driguez, H. Tetrahedron Lett. 1992, 33, 3125.
42. Derobertis, L.; Lancelon-Pin, C.; Driguez, H.; Attioui, F.; Bonaly, R.; Marsura, A. Bioorg. Med. Chem. Lett. 1994, 4, 1127.
43. Imata, H.; Kubota, K.; Hattori, K.; Aoyagi, M.; Jindoh, C. Bioorg. Med. Chem. Lett. 1997, 7, 109.
44. Matsuda, K.; Inazu, T.; Haneda, K.; Mizuno, M.; Yamanoi, T.; Hattori, K.; Yamamoto, K.; Kumagai, H. Bioorg. Med. Chem. Lett. 1997, 7, 2353.
45. Kassab, R.; Felix, C.; Parrot-López, H.; Bonaly, R. Tetrahedron Lett. 1997, 38, 7555.
46. Hattori, K.; Imata, H.; Kubota, K.; Matsuda, K.; Aoyagi, M.; Yamamoto, K.; Jindoh, C.; Yamanoi, T.; Inazu, T. J. Inclusion Phenom. Mol. Recogn. 1996, 25, 69.
47. Imata, H.; Kubota, K.; Hattori, K.; Aoyagi, M.; Jindoh, C. Polym. J. 1997, 29, 563.
48. Laine, V.; Costesarguet, A.; Gadelle, A.; Defaye, J.; Perly, B.; Djedainipilard, F. J. Chem. Soc., Perkin Trans. 2 1995, 1479.
49. Matta, K. L.; Girotra, R. N.; Barlow, J. J. Carbohydr. Res. 1975, 43, 101.
50. Horton, D. Methods Carbohydr. Chem. 1963, 2, 433.
51. Horton, D.; Wolfrom, M. L. J. Org. Chem. 1962, 27, 1794.
52. Robertis, L.; Lancelon-Pin, C.; Driguez, H. Bioorg. Med. Chem. Lett. 1994, 4, 1127.
53. (a) Pagé, D.; Zanini, D.; Roy, R. Bioorg. Med. Chem. 1996, 4, 1949.
54. (b) Pagé, D.; Roy, R. Bioorg. Med. Chem. Lett. 1996, 6, 1765.
55. (c) Pagé, D.; Roy, R. Glycoconjugate J. 1997, 14, 345.
56. (d) Pagé, D.; Roy, R. Int. J. Biochromatogr. 1997, 3, 231.
57. (e) Pagé, D.; Roy, R. Bioconjuagte Chem. 1997, 8, 714.
58. Ashton, P. R.; Koniger, R.; Stoddart, J. F.; Alker, D.; Harding, V. D. J. Org. Chem. 1996, 61, 903.
59. Liener, I. E.; Sharon, N.; Goldstein, I. J. The Lectins. Properties, Functions, and Applications in Biology and Medicine; Academic Press: New York, 1986.