Chiral dimeric capsules from N,C-linked peptidocalix[4]arenes self-assembled through an antiparallel β-sheetlike motif

Journal of the American Chemical Society

Volumn 126, Issue 20, 2004, Pages 6204-6205

  Sansone, Francesco ^a   Baldini, Laura ^a   Casnati, Alessandro ^a   Chierici, Elisa ^a   Faimani, Giovanni ^a   Ugozzoli, Franco ^a   Ungaro, Rocco ^a  

^a UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CARBON; NITROGEN; PEPTIDOCALIX[4]ARENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BETA SHEET; CHIRALITY; DIMERIZATION; MOLECULAR MODEL; NANOTECHNOLOGY; PROTEIN ASSEMBLY; PROTEIN MOTIF; STRUCTURE ANALYSIS; SUPRAMOLECULAR CHEMISTRY;

BRIDGED COMPOUNDS; CHLOROFORM; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHENOLS; SOLUTIONS;

EID: 2442690344     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja031511z     Document Type: Article

References (20)

1. Prins, L. J.; De Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. Shivanyuk, A.; Rebek, J. Chem. Commun. 2000, 8, 637-643. Böhmer, V.; Vysotsky, M. O. Austr. J. Chem. 2001, 54, 671-677. Rudkevich, D. M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; pp 155-180.
2. Prins, L. J.; De Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. Shivanyuk, A.; Rebek, J. Chem. Commun. 2000, 8, 637-643. Böhmer, V.; Vysotsky, M. O. Austr. J. Chem. 2001, 54, 671-677. Rudkevich, D. M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; pp 155-180.
3. Prins, L. J.; De Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. Shivanyuk, A.; Rebek, J. Chem. Commun. 2000, 8, 637-643. Böhmer, V.; Vysotsky, M. O. Austr. J. Chem. 2001, 54, 671-677. Rudkevich, D. M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; pp 155-180.
4. Prins, L. J.; De Jong, F.; Timmerman, P.; Reinhoudt, D. N. Nature 2000, 408, 181-184. Shivanyuk, A.; Rebek, J. Chem. Commun. 2000, 8, 637-643. Böhmer, V.; Vysotsky, M. O. Austr. J. Chem. 2001, 54, 671-677. Rudkevich, D. M. In Calixarenes 2001; Asfari, Z., Böhmer, V., Harrowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers: Dordrecht, 2001; pp 155-180.
5. Shimizu, K. D.; Rebek, J. Proc. Natl Acad Sci. U.S.A. 1995, 92, 12403-12407. Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. 2000, 39, 1264-1267.
6. Shimizu, K. D.; Rebek, J. Proc. Natl Acad Sci. U.S.A. 1995, 92, 12403-12407. Vysotsky, M. O.; Thondorf, I.; Böhmer, V. Angew. Chem., Int. Ed. 2000, 39, 1264-1267.
7. Corbellini, F.; Di Costanzo, L.; Crego-Calama, M.; Geremia, S.; Reinhoudt, D. N. J. Am. Chem. Soc. 2003, 125, 9946-9947.
8. Fochi, F.; Jacopozzi, P.; Wegelius, E.; Rissanen, K.; Cozzini, P.; Marastoni, E.; Fisicaro, E.; Manini, P.; Fokkens, R.; Dalcanale, E. J. Am. Chem. Soc. 2001, 123, 7539-7552.
9. Cram, D. J.; Choi, H.-J.; Bryant, J. A.; Knobler, C. B. J. Am. Chem. Soc. 1992, 114, 7748-7765.
10. Sánchez-Quesada, J.; Isler, M. P.; Ghadiri, M. R. J. Am. Chem. Soc. 2002, 124, 10004-10005.
11. Brewster and Shuker have reported (J. Am. Chem. Soc. 2002, 124, 7902-7903) on the self-association in polar media of a calix[4]arene tetraalanine derivative, originally synthesized by us.14 However, in this case the dimerization process seems to be promoted by the charged ammonium group of the amino acid.
12. Rincòn, A. M.; Prados, P.; de Mendoza, J. J. Am. Chem. Soc. 2001, 123, 3493-3498.
13. Castellano, R. K.; Nuckolls, C.; Rebek, J. J. Am. Chem. Soc. 1999, 121, 11156-11163.
14. Casnati, A.; Sansone, F.; Ungaro, R. Acc. Chem. Res. 2003, 36, 246-254.
15. Compound 3 and its dimethoxy analogue were synthesized, using a different strategy by Arimura, T.; Ide, S.; Nishioka, T.; Sugihara, H.; Murata, S.; Yamato, T. J. Chem. Res. S 2000, 5, 234-236 and G osztola, D.; Yamada, H.; Wasielewski, M. R. J. Am. Chem. Soc. 1995, 117, 2041-2048.
16. Compound 3 and its dimethoxy analogue were synthesized, using a different strategy by Arimura, T.; Ide, S.; Nishioka, T.; Sugihara, H.; Murata, S.; Yamato, T. J. Chem. Res. S 2000, 5, 234-236 and Gosztola, D.; Yamada, H.; Wasielewski, M. R. J. Am. Chem. Soc. 1995, 117, 2041-2048.
17. dimer are the calculated parameters.
18. Gellman, S. H. Curr. Opin. Chem. Biol. 1998, 2, 717-725. Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654-7661.
19. Gellman, S. H. Curr. Opin. Chem. Biol. 1998, 2, 717-725. Nowick, J. S.; Chung, D. M.; Maitra, K.; Maitra, S.; Stigers, K. D.; Sun, Y. J. Am. Chem. Soc. 2000, 122, 7654-7661.
20. Lazzarotto, M.; Sansone, F.; Baldini, L.; Casnati, A.; Cozzini, P.; Ungaro, Eur. J. Org. Chem. 2001, 595-602.