A hydrophilic cyclodextrin duplex forming supramolecular assemblies by physical cross-linking of a biopolymer

Chemistry - A European Journal

Volumn 13, Issue 31, 2007, Pages 8847-8857

  Bistri, Olivia ^a   Mazeau, Karim ^b   Auzély Velty, Rachel ^b   Sollogoub, Matthieu ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b CENTRE DE RECHERCHES SUR LES MACROMOLÉCULES VÉGÉTALES CERMAV CNRS   (France)

Author keywords

Calorimetry; Cyclodextrins; Molecular modeling; Physical cross linking; Viscometry

Indexed keywords

BIOPOLYMERS; CALORIMETRY; COMPLEXATION; CONFORMATIONS; CROSSLINKING; SUPRAMOLECULAR CHEMISTRY; SYNTHESIS (CHEMICAL); VISCOSITY MEASUREMENT;

HYDROPHILIC SPACERS; PHYSICAL CROSSLINKING;

CYCLODEXTRINS;

ADAMANTANE; BIOPOLYMER; CROSS LINKING REAGENT; CYCLODEXTRIN;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DIMERIZATION; HYDROPHOBICITY; MACROMOLECULE; MONTE CARLO METHOD; SYNTHESIS;

ADAMANTANE; BIOPOLYMERS; CARBOHYDRATE CONFORMATION; CROSS-LINKING REAGENTS; CYCLODEXTRINS; DIMERIZATION; HYDROPHOBICITY; MACROMOLECULAR SUBSTANCES; MODELS, CHEMICAL; MODELS, MOLECULAR; MONTE CARLO METHOD;

EID: 35748940325     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200700800     Document Type: Article

References (41)

1. a) R. Breslow, S. Chung, J. Am. Chem. Soc. 1990, 112, 9659;
2. b) R. Breslow, S. Halfon, B. Zhang, Tetrahedron 1995, 51, 377;
3. c) R. Breslow, B. Zhang, J. Am. Chem. Soc. 1996, 118, 8495.
4. M. R. de Jong, J. F. J. Engbersen, J. Huskens, D. N. Reinhoudt, Chem. Eur. J. 2000, 6, 4034.
5. a) Y. Liu, B. Li, C. C. You, T. Wada, Y. Inoue, J. Org. Chem. 2001, 66, 225;
6. b) Y. Liu, Y. Chen, S.-X. Liu, X.-D. Guan, T. Wada, Y. Inoue, Org. Lett. 2001, 3, 1657;
7. c) Y. Liu, Y. Song, Y. Chen, X. Q. Li, F. Ding, R. Q. Zhong, Chem. Eur. J. 2004, 10, 3685;
8. Y. Liu, H. M. Yu, Yv Chen, Y. L. Zhao, Chem. Eur. J. 2006, 12, 3858.
9. a) F. Venema, H. F. M. Nelissen, P. Berthault, N. Birlirakis, A. E. Rowan, M. C. Feiters, R. J. M. Nolte, Chem. Eur. J. 1998, 4, 2237;
10. b) F. Venema. A. E. Rowan, R. J. M. Nolte, J. Am. Chem. Soc. 1996, 118, 257.
11. H. Yamamur Y. a, S. Yamada, K. Kohno, N. Okuda, S. Araki, K. Kobayashi, R. Katakai, K. Kano, M. Kawai, J. Chem. Soc., Perkin Trans. 1 1999, 2943.
12. I. Tabushi, Y. Kuroda, K. Shimokawa, J. Am. Chem. Soc. 1979, 101, 1614;
13. R. Brelow, S. Chung, J. Am. Chem. Soc. 1990, 112, 9659;
14. R. Breslow, S. Halfon, B. Zhang, Tetrahedron 1995, 51, 377;
15. K. Sasaki, M. Nagasaka, Y. Kuroda, Chem. Commun. 2001, 2630.
16. a) T. Lecourt, A. J. Pearce, A. Herault, M. Sollogoub, P. Sinay, Chem. Eur. J. 2004, 10, 2960;
17. b) O. Bistri, P. Sinay, M. Sollogoub, Tetrahedron Lett. 2005, 46, 7757;
18. c) O. Bistri, P. Sinay, M. Sollogoub, Chem. Commun. 2006, 1112;
19. d) O. Bistri, P. Sinay, M. Sollogoub, Chem. Lett. 2006, 35, 534;
20. e) O. Bistri, P. Sinay, M. Sollogoub, Tetrahedron Lett. 2006, 47, 4137.
21. T. Lecourt, J.-M. Mallet, P. Sinay, Eur. J. Org. Chem. 2003, 4553;
22. O. Bistri, T. Lecourt, J.-M. Mallet, M. Sollogoub, P. Sinay, Chem. Biodiv. 2004, 1, 129.
23. T. Lecourt, P. Sinay, C. Chassenieux, M. Rinaudo, R. Auzély-Velty, Macromolecules 2004, 37, 4635.
24. T. Lecourt, J.-M. Mallet, P. Sinay, Tetrahedron Lett. 2002, 43, 5533.
25. M. Surzur, G. Torri, Bull. Soc. Chim. Fr. 1970, 3070;
26. M. Delgado, J. D. Martin, J. Org. Chem. 1999, 64, 4798.
27. S.-H. Chiu, D. C. Myles, R. L. Garrell, J. F. Stoddart, J. Org. Chem. 2000, 65, 2792.
28. J. B. Corbell, J. J. Lundquist, E. J. Toone, Tetrahedron: Asymmetry 2000, 11, 95.
29. A. Mulder, J. Huskens, D. N. Reinhoudt, Org. Biomol. Chem. 2004, 2, 3409.
30. K. Harata, Chem. Rev. 1998, 98, 1803.
31. R. Auzély-Velty, M. Rinaudo, Macromolecules 2002, 35, 7955.
32. D. P. Shoemaker, C. W. Garland, J. I. Steinfeld, Experiments in Physical Chemistry, 2nd ed., McGraw-Hill, New York, 1974, pp. 51-55.
33. 2, version 3.5, Molecular Simulations, San Diego, CA, 1997.
34. a) J. Maple, U. Dinur, A. T. Hagler, Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 5350;
35. b) J. R. Maple, Isr. J. Chem. 1994, 34, 195;
36. c) J. R. Maple, M. J. Hwang, T. P. Stockfisch, U. Dinur, M. Waldman, C. S. Ewing, A. T. Hagler, J. Comput. Chem. 1994, 15, 162;
37. d) H. Sun, Macromolecules 1995, 28, 701;
38. e) H. Sun, S. J. Mumby, J. R. Maple, A. T. Hagler, J. Am. Chem. Soc. 1994, 116, 2978.
39. A. K. Rappe, W. A. Goddard III, J. Phys. Chem. 1991, 95, 3358.
40. C. Betzel, W. Saenger, B. E. Hingerty, G. M. Brown, J. Am. Chem. Soc. 1984, 106, 7545.
41. L. Verlet, Phys. Rev. 1967, 159, 98.