Efficient synthesis of unsymmetrical bolaamphiphiles for spontaneous formation of vesicles and disks with a transmembrane organization

Langmuir

Volumn 17, Issue 3, 2001, Pages 613-618

  Guilbot, Jérôme ^a   Benvegnu, Thierry ^a   Legros, Nathalie ^a   Plusquellec, Daniel ^a   Dedieu, Jean Claude ^b   Gulik, Annette ^b  

^a Ecole de Chimie de Rennes   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; CONFORMATIONS; SYNTHESIS (CHEMICAL);

BOLAAMPHIPHILES; HYDROPHILICITY; HYDROPHOBICITY;

BIOLOGICAL MEMBRANES;

EID: 0034831184     PISSN: 07437463     EISSN: None     Source Type: Journal    
DOI: 10.1021/la000892g     Document Type: Article

References (35)

1. Fuhrhop, J. H.; Bach, R. Adv. Supramol. Chem. 1992, 2, 25.
2. Escamilla, G. H.; Newkome, G. R. Angew. Chem., Int. Ed. Engl. 1994, 33, 1937.
3. Zana, R. In Specialist Surfactants; Robb, I. D., Ed.; Chapman & Hall: Glasgow, 1996; p 81.
4. Fuhrhop, J. H.; Köning, J. In Membranes and Molecular Assemblies: The Synkinetic Approach; Stoddart, J. F., Ed.; Cambridge University Press: Cambridge, 1994.
5. Sprott, G. D. J. Bioenerg. Biomembr. 1992, 24, 555.
6. Gambacorca, A.; Gliozzi, A.; De Rosa, M. World J. Microbiol. Biotechnol. 1995, 11, 115.
7. Yamauchi, K.; Kinoshita, M. Prog. Polym. Sci. 1993, 18, 763.
8. De Rosa, R.; Morana, A. In Neural Networks and Biomolecular Engineering to Bioelectronics; Nicolini, N., Ed.; Plenum Press: New York, 1995; p 217.
9. Visscher, I.; Engberts, J. F. B. N. Langmuir 2000, 16, 52.
10. Yamada, M.; Ikeda, K.; Esumi, K.; Meguro, K. Langmuir 1990, 6, 949.
11. Kim, J. M.; Thomson, D. H. Langmuir 1992, 8, 637.
12. Menger, F. M.; Littau, C. A. J. Am. Chem. Soc. 1993, 115, 10083.
13. Lafont, D.; Boullanger, P.; Chevalier, Y. J. Carbohydr. Chem. 1995, 14, 533.
14. Gouéth, P.; Ramiz, A.; Ronco, G.; Mackenzie, G.; Villa, P. Carbohydr. Res. 1995, 266, 171.
15. Fyles, T. M.; Loock, D.; van Straaten Nijenhus, W. F.; Zhou, X. J. Org Chem. 1996, 67, 8866.
16. Song, L. D.; Rosen, M. J. Langmuir 1996, 12, 1149.
17. Nakatani, Y.; Yamamoto, M.; Diyizou, Y.; Warnock, W.; Dollé, V.; Haln, W.; Milon, A.; Ourisson, G. Chem. Eur. J. 1996, 2, 129.
18. Duivenvoorde, F. L.; Feiters, M. C.; van der Gaast, S. J.; Engberts, J. F. B. N. Langmuir 1997, 13, 3737.
19. Pestman, J. M.; Terpstra, K. R.; Stuart, M. C. A.; Van Doren, H. A.; Brisson, A.; Kellogg, R. M.; Engberts, J. B. F. N. Langmuir 1997, 13, 6857.
20. Eguchi, T.; Arakawa, K.; Terachi, T.; Kakinuma, K. J. Org. Chem. 1997, 62, 1924.
21. Bertho, J. N.; Coué, A.; Ewing, D. F.; Goodby, J. W.; Letellier, P.; Mackenzie, G.; Plusquellec, D. Carbohydr. Res. 1997, 300, 341.
22. Auzély-Velty, R.; Benvegnu, T.; Plusquellec, D.; Mackenzie, G.; Haley, J.A.; Goodby, J.W. Angew. Chem. Int. Ed. Engl. 1998, 37, 2511.
23. Kogiso, M.; Ohnishi, S.; Yase, K.; Masuda, M.; Shimizu, T. Langmuir 1998, 14, 4978.
24. Svenson, S.; Thompson, D. H. J. Org. Chem. 1998, 63, 7180.
25. Wang, G.; Hollingsworth, R. I. J. Org. Chem. 1999, 64, 4140.
26. Heiser, U. F.; Dobner, B. J. Chem. Soc., Perkin Trans. 1 1997, 809.
27. Fuhrhop, J. H.; David, H. H.; Mathieu, J.; Liman, U.; Winter, H. J.; Boekema, E. J. Am. Chem. Soc. 1986, 108, 1785.
28. Lecollinet, G.; Auzély-Velty, R.; Danel, M.; Benvegnu, T.; Mackenzie, G.; Goodby, J. W.; Plusquellec, D. J. Org. Chem. 1999, 64, 3139.
29. Bertho, J. N.; Ferrières, V.;Plusquellec, D. J. Chem. Soc., Chem. Commun. 1995, 1391.
30. Ferrières, V.; Bertho, J.N.; Plusquellec, D. Carbohydr. Res. 1998, 311, 25.
31. Floch, V.; Legros, N.; Loisel, S.; Guillaume, C.; Guilbot, J.; Benvegnu, T.; Ferrières, V.; Plusquellec, D.; Ferec, C. Biochem. Biophys. Res. Commun. 1998, 251, 360.
32. Roks, M. F.; Visser, H. G. J.; Zwikker, J. W.; Verkley, A. J.; Nolte, R. J. M. J. Am. Chem. Soc. 1983, 105, 4507.
33. Lo, S. L.; Chang, E. L. Biochem. Biophys. Res. Commun. 1990, 167, 238.
34. Berden, J. A.; Barker, R. W.; Radda, G. K. Biochim. Biophys. Acta 1975, 375, 186.
35. Moss, R. A.; Li, G.; Li, J. M. J. Am. Chem. Soc. 1994, 116, 805.