Self-assembly and stability of double rosette nanostructures with biological functionalities

Organic and Biomolecular Chemistry

Volumn 3, Issue 20, 2005, Pages 3727-3733

  Ten Cate, Mattijs G J ^a   Omerović, Merdan ^a   Oshovsky, Gennady V ^a   Crego Calama, Mercedes ^a   Reinhoudt, David N ^a  

^a UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; HYDROGEN BONDS; NANOSTRUCTURED MATERIALS; POLYPEPTIDES; SELF ASSEMBLY; THERMODYNAMIC STABILITY;

BARBITURIC ACID; CYANURIC ACID DERIVATIVES;

AMINES;

AMINE; AMINO ACID; BARBITURIC ACID; BARBITURIC ACID DERIVATIVE; CALIX(4)ARENE; CALIXARENE; CARBOHYDRATE; CYANURIC ACID; MELAMINE; NANOMATERIAL; PEPTIDE; PHENOL DERIVATIVE; TRIAZINE DERIVATIVE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; HYDROGEN BOND; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

AMINES; AMINO ACIDS; BARBITURATES; CALIXARENES; CARBOHYDRATES; CIRCULAR DICHROISM; HYDROGEN BONDING; MOLECULAR CONFORMATION; NANOSTRUCTURES; PEPTIDES; PHENOLS; STEREOISOMERISM; THERMODYNAMICS; TRIAZINES;

EID: 27744537419     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508449k     Document Type: Article

References (34)

1. (a) R. Fiammengo, M. Crego-Calama and D. N. Reinhoudt, Curr. Opin. Chem. Biol., 2001, 5, 660-673;
2. (b) M. Crego-Calama and D. N. Reinhoudt, Science, 2002, 295. 2403-2407.
3. G. M. Whitesides, E. E. Simanek, J. P. Mathias, C. T. Seto, D. N. Shin, M. Mammen and D. M. Gordon, Acc. Chem. Res., 1995, 28, 37-44.
4. (a) E. Benjamini, G. Sunshine, S. Leskowitz, Immunology, A Short Course, 3rd edn. Wiley, New York, 1996;
5. (b) L. Stryer, Biochemistry, 4th edn, Freeman and Company: New York, 1995.
6. P. Timmerman and D. N. Reinhoudt. Adv. Mater., 1999, 11, 71-74.
7. (a) R. H. Vreekamp, R. H. Van Duynhoven, M. Hubert, W. Verboom and D. N. Reinhoudt, Angew. Chem., Int. Ed., 1996, 35, 1215-1218;
8. (b) P. Timmerman, K. A. Jollife, M. Crego-Calama, J. L. Weidmann, L. J. Prins, F. Cardullo, B. H. M. Snellink-Ruel, R. H. Fokkens, N. M. M. Nibbering, S. Shinkai and D. N. Reinhoudt, Chem. Eur. J., 2000, 6, 4104-4115.
9. J. M. C. A. Kerckhoffs, M. Crego-Calama, I. Luyten, P. Timmerman and D. N. Reinhoudt, Org. Lett., 2000, 2, 4121-4124.
10. (a) C. T. Seto and G. M. Whitesides. J. Am. Chem. Soc., 1990, 112, 6409-6411;
11. (b) J. A. Zerkowski, C. T. Seto, D. A. Wierdo and G. M. Whitesides, J. Am. Chem. Soc., 1990, 112, 9025 9026.
12. P. Timmerman, R. H. Vreekamp, R. Hulst, W. Verboom, D. N. Reinhoudt, K. Risannen, K. A. Udachin and J. Ripmeester, Chem. Eur. J., 1997, 3. 1823-1832.
13. J. M. C. A. Kerckhoffs, M. Crego-Calama, I. Luyten, P. Timmerman and D. N. Reinhoudt, Org. Lett., 2000, 2, 4121 4124.
14. T. Ishi-i, M. Crego-Calama, P. Timmerman, D. N. Reinhoudt and S. Shinkai, J. Am. Chem. Soc., 2002, 124, 14631-14641.
15. (a) I. Yamamoto, K. Fukui, S. Yamamoto, K. Ohta and K. Matsuzaki, Synthesis, 1985, 686-688;
16. (b) H. Ogura and H. Takahashi, Heterocycles, 1982, 87-90;
17. (c) G. V. Oshovsky, W. Verboom, R. H. Fokkens and D. N. Reinhoudt, Chem. Eur. J., 2004, 10, 2739-2748.
18. (a) P. Timmerman and L. J. Prins. Eur. J. Org. Chem., 2001, 17, 3191-3205;
19. (b) D. N. Reinhoudt, P. Timmerman, F. Cardullo, M. Crego-Calama, NATO Science Series C, vol 257, ed. R. Ungaro, E. Dalcanale, Kluwer Academic Publishers, Dordrecht, 1999; pp. 181-195.
20. 6 is used as standard, for which this ratio was arbitrarily set to 100%.
21. K. A. Jolliffe, M. Crego-Calama, R. Fokkens, N. M. M. Nibbering, P. Timmerman and D. N. Reinhoudt, Angew. Chem., Int. Ed., 1998, 37, 1247-1251.
22. Detailed analyses of energetic parameters are described in M. G. J. Ten Cate, J. Huskens, M. Crego-Calama and D. N. Reinhoudt, Chem. Eur. J., 2004, 10, 3632-3639.
23. M. Mammen, E. E. Simanek and G. M. Whitesides, J. Am. Chem. Soc., 1996, 118, 12614-12623.
24. (a) L. J. Prins, K. A. Jolliffe, R. Hulst, P. Timmerman and D. N. Reinhoudt, J. Am. Chem. Soc., 2000, 122, 3617-3627;
25. (b) L. J. Prins, J. Huskens, F. De Jong, P. Timmerman and D. N. Reinhoudt, Nature, 1999, 398, 498-502;
26. (c) L. J. Prins, F. De Jong, P. Timmerman and D. N. Reinhoudt, Nature, 2000, 408, 181-184.
27. (a) A. Varki, Glycobiology, 1993, 3, 97-130;
28. (b) R. A. Dwek, Chem. Rev., 1996, 96, 683-720;
29. (c) M. Mammen, S.-K. Choi and G. M. Whitesides, Angew. Chem., Int. Ed., 1998, 37, 2754-2794.
30. A. G. Bielejewska, C. E. Marjo, L. J. Prins, P. Timmerman, F. De Jong and D. N. Reinhoudt, J. Am. Chem. Soc., 2001, 123, 7518-7533.
31. L. J. Prins, Non-Covalent Synthesis of Chiral Hydrogen-Bonded Assemblies, University of Twente, Enschede, The Netherlands, ISBN 90-365-1627-7, 2001.
32. 1H NMR spectroscopy, but these assemblies are hardly CD active because either the opposite chirality inducing components strongly affect the orientation of the chromophores responsible for the CD activity or coincidentally cause opposite CD activity of identical intensity.
33. K. K. L. Cheuk, J. W. Y. Lam, L. M. Lai, Y. Dong and B. Z. Tang, Macromolecules, 2003, 36, 9752-9762.
34. M. G. J. Ten Cate, M. Crego-Calama and D. N. Reinhoudt, J. Am. Chem. Soc., 2004, 126, 10840-10841.