Novel amphiphilic cyclic oligosaccharides: Synthesis and self-aggregation properties

Journal of Organic Chemistry

Volumn 72, Issue 25, 2007, Pages 9679-9689

  Coppola, Cinzia ^a   Saggiomo, Vittorio ^a   Di Fabio, Giovanni ^a   De Napoli, Lorenzo ^a   Montesarchio, Daniela ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AGGLOMERATION; AMPHIPHILES; CONCENTRATION (PROCESS); ESTERS; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS (CHEMICAL);

AMPHIPHILIC CYCLIC OLIGOSACCHARIDES; MILLIMOLAR RANGE; PHOSPHODIESTER LINKAGES;

OLIGOSACCHARIDES;

ESTER DERIVATIVE; MACROCYCLIC COMPOUND; OLIGOSACCHARIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CONCENTRATION (PARAMETERS); LIPOPHILICITY; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

CARBOHYDRATE CONFORMATION; MAGNETIC RESONANCE SPECTROSCOPY; OLIGOSACCHARIDES; STEREOISOMERISM; SURFACE-ACTIVE AGENTS;

EID: 36849081346     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo7017087     Document Type: Article

References (39)

1. For a recent review, see for example: Costamagna, J.; Ferraudi, G.; Matsuhiro, B.; Campos-Vallette, M.; Canales, J.; Villagran, M.; Vargas, J.; Aguirre, M. J. Coord. Chem. Rev. 2000, 196, 125-164.
2. Molotov, Y.A. Macrocyclic Compounds in Analytical Chemistry; Wiley: New York, 1997.
3. Szejtli, J. Chem. Rev. 1998, 98, 1743-1753 and references therein.
4. Hedges, A. R. Chem. Rev. 1998, 98, 2035-2044.
5. Jullien, L.; Lazrak, T.; Canceill, J.; Lacombe, L.; Lehn, J. M. J. Chem. Soc., Perkin Trans. 2 1993, 1011-1020.
6. Bacri, L.; Benkhaled, A.; Guegan, P.; Auvray, L. Langmuir 2005, 21, 5842-5846.
7. Madhavan, N.; Robert, E. C.; Gin, M. S. Angew. Chem., Int. Ed. 2005, 44, 7584-7587.
8. (a) Ravoo, B. J.; Darcy, R. Angew. Chem., Int. Ed. 2000, 39, 4324-4326.
9. (b) Donohue, R.; Mazzaglia, A.; Ravoo, B. J; Darcy, R. Chem. Commun. 2002, 2864-2865.
10. (c) Mazzaglia, A.; Ravoo, B. J.; Darcy, R.; Gambadauro, P.; Mallamace, F. Langmuir 2002, 18, 1945-1948.
11. (d) Nolan, D.; Darcy, R.; Ravoo, B. J. Langmuir 2003, 19, 4469-4472.
12. (e) Falvey, P.; Lim, C. W.; Darcy, R.; Revermann, T.; Karst, U.; Giesbers, M.; Marcelis, A. T. M.; Lazar, A.; Coleman, A. W.; Reinhoudt, D. N.; Ravoo, B. J. Chem. - Eur. J. 2005, 11, 1171-1180.
13. (a) Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919-1958.
14. (b) Khan, A. R.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977-1996.
15. (c) Easton, C. J.; Lincoln, S. F. Modified Cyclodextrins: Scaffolds and Templates for Supramolecular Chemistry; Imperial College Press: London, 1999.
16. For a recent work describing per-2,3-di-O-alkylated cyclodextrins, see for example: Badi, N.; Jarroux, N.; Guégan, P. Tetrahedron Lett. 2006, 47, 8925-8927.
17. (a) Locardi, E.; Stockle, M.; Gruner, S.; Kessler, H. J. Am. Chem. Soc. 2001, 123, 8189-8196.
18. (b) van Well, R. M.; Marinelli, L.; Erkelens, K.; van der Marel, G. A.; Lavecchia, A.; Overkleeft, H. S.; van Boom, J. H.; Kessler, H.; Overhand, M. Eur. J. Org. Chem. 2003, 2303-2313.
19. (c) Bornaghi, L. F.; Wilkinson, B. L.; Kiefel, M. J.; Poulsen, S. A. Tetrahedron Lett. 2004, 45, 9281-9284.
20. (d) Mayes, B. A.; Stetz, R. J. E.; Ansell, C. W. G.; Fleet, G. W. J. Tetrahedron Lett. 2004, 45, 153-156.
21. Fan, L.; Hindsgaul, O. Org. Lett. 2002, 4, 4503-4506.
22. (a) Stichler-Bonaparte, J.; Vasella, A. Helv. Chim. Acta 2001, 84, 2355-2367.
23. (b) Hoffmann, B.; Bernet, B.; Vasella, A. Helv. Chim. Acta 2002, 85, 265-287.
24. (a) Bodine, K. D.; Gin, D. Y.; Gin, M. S. J. Am. Chem. Soc. 2004, 126, 1638-1639.
25. (b) Bodine, K. D.; Gin, D. Y.; Gin, M. S. Org. Lett. 2005, 7, 4479-4482.
26. (a) Di Fabio, G.; Randazzo, A.; D'Onofrio, J.; Ausìn, C.; Grandas, A.; Pedroso, E.; De Napoli, L.; Montesarchio, D. J. Org. Chem. 2006, 9, 3395-3408.
27. (b) D'Onofrio, J.; Coppola, C.; Di Fabio, G.; De Napoli, L.; Montesarchio, D. Eur. J. Org. Chem. 2007, 3849-3858.
28. Terreros, A.; Galera Gomez, P. A.; Lopez Cabarcos, E.; Muller, A. Colloids Surf., A 2000, 164 (1), 47-53.
29. Rumney, S. IV; Kool, E. T. J. Am. Chem. Soc. 1995, 117, 5635-5646.
30. Adinolfi, M.; De Napoli, L.; Di Fabio, G.; Iadonisi, A.; Montesarchio, D. Org. Biomol. Chem. 2004, 2, 1879-1886.
31. Alazzouzi, E. M.; Escaja, N.; Grandas, A.; Pedroso, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 1506-1508.
32. Moggio, L.; De Napoli, L.; Di Blasio, B.; Di Fabio, G.; D'Onofrio, J.; Montesarchio, D.; Messere A. Org. Lett. 2006, 8 (10), 2015-2018.
33. (a) Jung, J. H.; John, G.; Masuda, M.; Yoshida, K.; Shinkai, S.; Shimizu, T. Langmuir 2001, 17, 7229-7232.
34. (b) Nie, X.; Wang, G. J. Org. Chem. 2006, 71, 4734-4741.
35. (c) John, G.; Zhu, G.; Li, J.; Dordick, J. S. Angew. Chem., Int. Ed. 2006, 45, 4772-4775.
36. (a) Stafford, R. E.; Fanni, T.; Dennis, E. A. Biochemistry 1989, 28, 5113-5120.
37. (b) Babu, P.; Chopra, D.; Guru Row, T. N.; Maitra, U. Org. Biomol. Chem. 2005, 3, 3695-3700.
38. Lasie, D. D. Liposomes: from Physics to Applications; Elsevier: Amsterdam, 1993.
39. Rivaille, R.; Szabó, L. Bull. Soc. Chim. Fr. 1963, 716-721.