Thermoregulated optical properties of peptidic pseudorotaxanes

Angewandte Chemie - International Edition

Volumn 39, Issue 1, 2000, Pages 143-145

  Meillon, Jean Christophe ^a   Voyer, Normand ^a   Biron, Éric ^a   Sanschagrin, François ^a   Stoddart, J Fraser ^b  

^a UNIVERSITÉ LAVAL   (Canada)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Circular dichroism; Peptides; Receptors; Rotaxanes; Supramolecular chemistry

Indexed keywords

CROWN ETHER; ROTAXANE; TAXANE DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CIRCULAR DICHROISM; MASS SPECTROMETRY; OPTICAL ROTATION; SYNTHESIS; TEMPERATURE;

EID: 0034598510     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000103)39:1<143::AID-ANIE143>3.0.CO;2-R     Document Type: Article

References (24)

1. D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196, and references therein.
2. D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196, and references therein.
3. a) P. R. Ashton, S. E. Boyd, C. G. Claessens, R. E. Gillard, S. Menzer, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 788-798;
4. b) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944;
5. b) R. Jäger, F. Vögtle, Angew. Chem. 1997, 109, 966-980; Angew. Chem. Int. Ed. Engl. 1997, 36, 930-944;
6. c) J.-P. Sauvage, C. O. Dietrich-Buchecker, J.-C. Chambron in Comprehensive Supramolecular Chemistry, Vol. 9 (Ed.: J.-M. Lehn), Pergamon, Oxford, 1996, p. 43;
7. d) D. G. Hamilton, J. E. Davies, L. Prodi, J. K. M. Sanders, Chem. Eur. J. 1998, 4, 608-620.
8. For reviews, see: a) N. Voyer, Top. Curr. Chem. 1996, 184, 1-37;
9. b) N. Voyer, J. Lamothe, Tetrahedron 1995, 34, 9241-9284.
10. Recently, Leigh reported the formation of an achiral rotaxane and molecular shuttle incorporating a Gly-Gly dipeptide: a) D. A. Leigh, A. Murphy, J. P. Smart, M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732;
11. Recently, Leigh reported the formation of an achiral rotaxane and molecular shuttle incorporating a Gly-Gly dipeptide: a) D. A. Leigh, A. Murphy, J. P. Smart, M. Z. Slawin, Angew. Chem. 1997, 109, 752-756; Angew. Chem. Int. Ed. Engl. 1997, 36, 728-732;
12. b) S. A. Lane, D. A. Leigh, A. Murphy, J. Am. Chem. Soc. 1997, 119, 11 092-11 093.
13. a) N. Voyer, J. Roby, D. Deschênes, J. Bernier, Supramol. Chem. 1995, 5, 61-69;
14. b) N. Voyer, B. Guérin, Tetrahedron 1994, 4, 989-1010;
15. c) N. Voyer, J. Am. Chem. Soc. 1991, 113, 1818-1821.
16. a) P. R. Ashton, M. C. T. Fyfe, P. T. Glink, S. Menzer, J. F. Stoddart, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 12 514-12 524;
17. b) P. R. Ashton, P. T. Glink, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 729-736.
18. P. R. Ashton, E. J. T. Chrystal, P. T. Glink, S. Menzer, C. Schiavo, N. Spencer, J. F. Stoddart, P. A. Tasker, A. J. P. White, D. J. Williams, Chem. Eur. J. 1996, 2, 709-728.
19. P. R. Ashton, R. Ballardini, V. Balzani, M. Gómez-López, S. E. Lawrence, M. V. Martínez-Díaz, M. Montalti, A. Piersanti, L. Prodi, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1997, 119, 10 641-10 651.
20. M. C. Manning, Biocatalyst Design for Stability and Specificity, American Chemical Society, Washington, DC, 1993, chap. 3.
21. R. W. Woody, Peptides, Polypeptides, and Proteins, Wiley, New York, NY, 1986, pp. 339-350.
22. Measured at 45 °C and assuming the formation of 1:1 complex only. M. P. Mack, R. R. Richardson, R. A. Palmer, R. G. Ghirardelli, J. Am. Chem. Soc. 1976, 98, 7830-7832.
23. Modeling was performed using MOE software from the Chemical Computing Group (www.chemcomp.com) using a CVFF-91 force field.
24. It is likely that the most stable structure of [A·1] shown in Figure 4 is accompanied by one or more other β-turn complexes in solution. This would explain the difficulties in crystallizing [A·1] and discrepancies in the NMR integrations.