Selection between pinching-type and supramolecular polymer-type complexes by α-cyclodextrin-β-cyclodextrin hetero-dimer and hetero-cinnamamide guest dimers

Journal of Organic Chemistry

Volumn 71, Issue 13, 2006, Pages 4878-4883

  Takahashi, Hirokazu ^a   Takashima, Yoshinori ^a   Yamaguchi, Hiroyasu ^a   Harada, Akira ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ADAMANTYL GROUPS; CYCLODEXTRIN; HETERO-CINNAMAMIDE; SUPRAMOLECULAR COMPLEXES;

ATOMIC FORCE MICROSCOPY; DIMERS; MIXTURES; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERS; PROTEINS; SUPRAMOLECULAR CHEMISTRY;

COMPLEXATION;

ALPHA CYCLODEXTRIN; AMIDE; BETA CYCLODEXTRIN; CINNAMAMIDE; CINNAMIC ACID DERIVATIVE; FUNCTIONAL GROUP; HETERODIMER; POLYMER; TERT BUTYLOXYCARBONYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC FORCE MICROSCOPY; CIRCULAR DICHROISM; COMPLEX FORMATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; PULSE FIELD GRADIENT SPIN ECHO NUCLEAR MAGNETIC RESONANCE; ROESY NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUPRAMOLECULAR CHEMISTRY;

ALPHA-CYCLODEXTRINS; BETA-CYCLODEXTRINS; CINNAMATES; CIRCULAR DICHROISM; DIMERIZATION; MACROMOLECULAR SUBSTANCES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ATOMIC FORCE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; POLYMERS; REFERENCE STANDARDS; SENSITIVITY AND SPECIFICITY;

EID: 33745466694     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0604686     Document Type: Article

References (27)

1. Aggeli, A.; Bell, M.; Boden, N.; Keen, J. N.; Knowles, P. F.; McLeish, T. C. B.; Pitkeathly, M.; Radford, S. E. Nature 1997, 386, 259-262.
2. (a) Amos, L. A.; Baker, T. S. Nature 1979, 279, 607-612.
3. (b) Luduena, R. F. Mol. Biol. Cell 1993, 4, 445-457.
4. (c) Stullivan, K. F. Annu. Rev. Cell Biol. 1988, 4, 687-716.
5. (d) Wade, R. H.; Chrëtien, D. J. Struct. Biol. 1993, 110, 1-27.
6. (a) Yamaguchi, N.; Gibson, H. W. Angew. Chem., Int. Ed. 1999, 38, 143.
7. (b) Yamaguchi, N.; Nagvekar, D. S.; Gibson, H. W. Angew. Chem., Int. Ed. 1998, 37, 2361.
8. (c) Gibson, H. W.; Yamaguchi, N.; Jones, J. W. J. Am. Chem. Soc. 2003, 125, 3522.
9. (a) Pease, A. R.; Jeppeson, J. O.; Stoddart, J. F.; Lop, Y. I.; Collier, C. P.; Heath, J. R. Acc. Chem. Res. 2001, 34, 433.
10. (b) Harada, A. Acc. Chem. Res. 2001, 34, 456.
11. (c) Harada, A.; Kawaguchi, Y.; Hoshino, T. J. Inclusion Phenom. Macrocyclic Chem. 2001, 41, 115.
12. (d) Miyauchi, M.; Takashima, Y.; Yamaguchi, H.; Harada, A. J. Am. Chem. Soc. 2005, 127, 2984-2989.
13. Mulder, A.; Reinhoudt, D. N. Chem. Commun. 2002, 22, 2734-2735.
14. (a) Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry, Springer: Berlin, 1978.
15. (b) Bender, M. L.; Bergeron, R. J.; Komiyama, M. The Bioorganic Chemistry of Enzymatic Catalysis; Wiley: New York, 1984.
16. (a) Breslow, R. Acc. Chem. Res. 1991, 24, 317.
17. (b) Zhang, B.; Breslow, R. J. Am. Chem. Soc. 1997, 119, 1676-1681.
18. (c) Breslow, R.; Zhang, X.; Huang, Y. J. Am. Chem. Soc. 1997, 119, 4535-4536.
19. (a) Wang, Y.; Ueno, A.; Toda, F. Chem. Lett. 1994, 167-170.
20. (b) Ikeda, H.; Nishikawa, S.; Takao, J.; Akiike, T.; Yamamoto, Y.; Ueno, A.; Toda, F. J. Inclusion Phenom. Macrocyclic Chem. 1996, 25, 133-136.
21. Lock, J. S.; May, B. L.; Clements, P.; Lincoln, S. T.; Easton, C. J. J. Inclusion Phenom. Macrocyclic Chem. 2004, 50, 13-18.
22. (a) Hasegawa, Y.; Miyauchi, M.; Takashima, Y.; Yamaguchi, H.; Harada, A. Macromolecules 2005, 38, 3724-3730.
23. (b) Ohga, K.; Takashima, Y.; Takahashi, H.; Kawaguchi, Y.; Yamaguchi, H.; Harada, A. Macromolecules 2005, 38, 5897-5904.
24. Generally, the cationic compounds are not included in the CD cavity. Previously, we have studied the formation inclusion complexes between the viologen polymers and the a-CD. These results indicated that the cationic groups play a rule in the electron stopper and were not included in the α-CD caviry.
25. (a) Kawaguchi, Y.; Harada, A. J. Am. Chem. Soc. 2000, 122, 3797-3798.
26. (b) Kawaguchi, Y.; Harada, A. Org. Lett. 2000, 2, 1353-1356.
27. 2O. were added to the solution of the mixture of α-CD-β-CD dimer and G-t-Boc guest dimer.