Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl-Azido Trisaccharide

Journal of the American Chemical Society

Volumn 126, Issue 6, 2004, Pages 1638-1639

  Bodine, Kyle D ^a   Gin, David Y ^a   Gin, Mary S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

8 ANILINO 1 NAPHTHALENESULFONIC ACID; ALKYNE; AZIDE; CYCLODEXTRIN DERIVATIVE; MACROCYCLIC COMPOUND; MANNOSE; TRISACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CYCLIZATION; CYCLODIMERIZATION; DIMERIZATION; FLUORESCENCE; GLYCOSYLATION; HYDROGENOLYSIS; REACTION ANALYSIS;

EID: 1242269270     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039374t     Document Type: Article

References (32)

1. Takahashi, K. Chem. Rev. 1998, 98, 2013.
2. (a) Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997.
3. (b) Rizzarelli, E.; Vecchio, G. Coord. Chem. Rev. 1999, 188, 343.
4. Harada, A. Acc. Chem. Res. 2001, 34, 456.
5. (a) Ferancova, A.; Labuda, J. Fresenius J. Anal. Chem. 2001, 370, 1.
6. (b) Willner, I.; Willner, B. J. Mater. Chem. 1998, 8, 2543.
7. Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977.
8. Teranishi, K. Tetrahedron 2003, 59, 2519.
9. Atsumi, M.; Izumida. M.; Yuan, D.-Q.; Fujita, K. Tetrahedron Lett. 2000, 41, 8117.
10. Poorters, L.; Armspach, D.; Matt, D. Eur. J. Org. Chem. 2003, 1377.
11. Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919.
12. (a) Mori, M.; Ito, Y.; Uzawa, J.; Ogawa, T. Tetrahedron Lett. 1990, 31, 3191.
13. (b) Mori, M.; Ito, Y.; Ogawa, T. Carbohydr. Res. 1989, 192, 131.
14. (c) Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265.
15. Chong, P. Y.; Petillo, P. A. Org. Lett. 2000, 2, 1093.
16. Sakairi, N.; Kuzuhara, H. J. Chem. Soc., Chem. Commun. 1993, 1874.
17. (a) Huisgen, R.; Knorr, R.; Mobius, L.; Szeimies, G. Chem. Ber. 1965, 98, 4014.
18. (b) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004.
19. (c) Peto, C.; Batta, G.; Gyorgydeak, Z.; Sztaricskai, F. J. Carbohydr. Chem. 1996, 15, 465.
20. (d) Katritsky, A. R.; Zhang, Y.; Singh, S. K. Heterocycles 2003, 60, 1225.
21. Garcia, B. A.; Gin, D. Y. J. Am. Chem. Soc. 2000, 122, 4269.
22. Maintaining the reaction temperature below -20°C allows acid-catalyzed post-coupling anomerization to afford the desired α-anomer as the sole product.
23. (a) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
24. (b) Pérez-Balderas, F.; Ortega-Muñoz, O.; Morales-Sanfrutos, J.; Hernández-Mateo, F.; Calvo-Flores, F. G.; Calvo-Asín, J. A.; Isac-García, J.; Santoyo-Gonzáles, F. Org. Lett. 2003, 5, 1951.
25. (c) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
26. Saenger, W.; Jacob, J.; Gessler, K.; Steiner, T.; Hoffimann, D.; Sanbe, H.; Koizumi, K.; Smith, S. M. Takaha, T. Chem. Rev. 1998, 98, 1787.
27. Rekharsky, M. V.; Inoue, Y. Chem. Rev. 1998, 98, 1875.
28. Ebbesen, T. W.; Ghiron, C. A. J. Phys. Chem. 1989, 93, 7139.
29. Nishijo, J.; Nagai, M.; Yasuda, M. Carbohydr. Res. 1993, 245, 43.
30. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; John Wiley & Sons: New York. 1987.
31. Nishijo, J.; Nagai, M. J. Pharm. Sci. 1991, 80, 58.
32. 2O displayed complexation induced shifts (CIS) for both compounds. Those for ANS were of different magnitude and occasionally different direction compared to the CIS of ANS with β-CD. This highlights that the specific structure of the complex of ANS + 1 is distinct from that of ANS + β-CD. Further studies to explore the solution structure of 1 and its complexes are currently underway.