Self-assembly of a water-soluble [2]rotaxane with carbohydrate stoppers

Tetrahedron Letters

Volumn 38, Issue 32, 1997, Pages 5691-5694

  Ashton, Peter R ^a   Everitt, Simon R L ^a   Gómez López, Marcos ^a   Jayaraman, Narayanaswamy ^a   Stoddart, J Fraser ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

MACROCYCLIC COMPOUND;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

EID: 0030858648     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01247-1     Document Type: Article

References (27)

1. a) Harrison, I.T. J. Chem. Soc., Chem. Commun. 1972, 231-232.
2. b) Harrison, I.T. J. Chem. Soc., Perkin Trans. 1 1974, 301-304.
3. a) Ashton, P.R.; Belohradsky, M.; Philp, D.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1993, 1269-1274.
4. b) Ashton, P.R.; Belohradsky, M.; Philp, D.; Spencer, N.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1993, 1274-1277.
5. a) Amabilino, D.B.; Stoddart, J.F. Chem. Rev. 1995, 95, 2229-2260.
6. b) Belohradsky, M.; Raymo, F.M.; Stoddart, J.F. Collect. Czech. Chem. Commun. 1996, 61, 1-43.
7. c) Philp, D.; Stoddart, J.F. Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
8. a) Amabilino, D.B.; Ashton, P.R.; Belohradsky, M.; Raymo, F.M.; Stoddart, J.F. J. Chem. Soc., Chem. Commun. 1995, 751-753.
9. b) Ashton, P.R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M.T.; Philp, D.; Prodi, L.; Raymo, F.M.; Reddington, M.V.; Spencer, N.; Stoddart, J.F.; Venturi, M.; Williams, D.J. J. Am. Chem. Soc. 1996, 118, 4931-4951.
10. c) Asakawa, M.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M.T.; Kocian, O.; Prodi, L.; Raymo, F.M.; Stoddart, J.F.; Venturi, M. J. Am. Chem. Soc. 1997, 119, 302-310.
11. During the preparation of this manuscript, a report on the synthesis of a [2]rotaxane with carbohydrate stoppers came to our attention. See: Archut, A.; Müller, M.W.; Baumann, S.; Habel, M.; Vögtle, F. Liebigs Ann. 1997, 495-499.
12. Anelli, P.L.; Ashton, P.R.; Ballardini, R.; Balzani, V.; Delgado, M.; Gandolfi, M.T.; Goodnow, T.T.; Kaifer, A.E.; Philp, D.; Pietraszkiewicz, M.; Prodi, L.; Reddington, M.V.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Vicent, C.; Williams, D.J. J. Am. Chem. Soc. 1992, 114, 193-218.
13. 13C NMR spectroscopies.
14. +.
15. +.
16. The salt 7.4Cl behaves as a receptor in aqueous solution for biologically-important compounds, such as amino acids and neurotransmitters. See: a) Goodnow, T.T.; Reddington, M.V.; Stoddart, J.F.; Kaifer, A.E. J. Am. Chem. Soc. 1991, 113, 4335-4337.
17. b) Bernardo, A.R.; Stoddart, J.F.; Kaifer, A.E. J. Am. Chem. Soc. 1992, 114, 10624-10631.
18. Anderson, S.; Anderson, H.L. Angew. Chem. Int. Ed. Engl. 1996, 35, 1956-1959.
19. a) Ashton, P.R.; Boyd, S.E.; Brown, C.L.; Jayaraman, N.; Nepogodiev, S.A.; Stoddart, J.F. Chem. Eur. J. 1996, 2, 115-1128.
20. b) Ashton, P.R.; Boyd, S.E.; Brown, C.L.; Jayaraman, N.; Stoddart, J.F. Angew. Chem. Int. Ed. Engl. 1997, 36, 732-735.
21. c) Ashton, P.R.; Boyd, S.E.; Brown, C.L.; Nepogodiev, S.A.; Meijer, E.W.; Peerlings, H.W.I., Stoddart, J.F. Chem. Eur. J. 1997, In press.
22. d) Jayaraman, N.; Nepogodiev, S.A.; Stoddart, J.F. Chem. Eur. J. 1997, In press.
23. a) Masuda, M.; Shimizu, T. Chem. Commun. 1996, 1057-1058.
24. b) Shimizu, T.; Kogiso, M.; Masuda, M. Nature (London) 1996, 383, 487-488.
25. c) Shimizu, T.; Masuda, M. J. Am. Chem. Soc. 1997, 119, 2812-2818.
26. Ahlers, M.; Muller, W.; Reichert, A.; Ringsdorf, H.; Venzmer, J. Angew. Chem. Int. Ed. Engl. 1990, 29, 1269-1285.
27. Asakawa, M.; Everitt, S.R.L.; Jayaraman, N.; Gómez-López, M.; Shimizu, T.; Stoddart, J.F.; Yase, K. Unpublished electron microscopy studies.