Highly negative homotropic allosteric binding of viologens in a double-cavity porphyrin

Journal of the American Chemical Society

Volumn 125, Issue 5, 2003, Pages 1186-1187

  Thordarson, Pall ^a   Bijsterveld, Edward J A ^a   Elemans, Johannes A A W ^a   Kasák, Peter ^a   Nolte, Roeland J M ^a   Rowan, Alan E ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN; VIOLOGEN;

ALLOSTERISM; ARTICLE; MOLECULAR INTERACTION; OXYGEN AFFINITY; SPECTROSCOPY; SYNTHESIS; TITRIMETRY;

BIOMIMETIC MATERIALS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; PORPHYRINS; SPECTROMETRY, FLUORESCENCE; SPECTROPHOTOMETRY, ULTRAVIOLET; THERMODYNAMICS; VIOLOGENS;

EID: 0037419823     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja028463n     Document Type: Article

References (21)

1. (a) Shinkai, S.; Ikeda, M.; Suzasaki, A.; Takeuchi, M. Acc. Chem. Res. 2001, 34. 494.
2. (b) Takeuchi, M.; Ikeda, M.; Sugasaki. A.: Shinkai, S. Acc. Chem. Res. 2001, 34, 865.
3. (a) Perlmutter-Hayman, B. Acc. Chem. Res. 1986, 19, 90.
4. Connors, K. A. Binding Constants; John Wiley & Sons: New York. 1987.
5. (a) Monod, J.; Changeux, J.-P.; Jacob, F. J. Mol. Biol. 1963, 6, 306.
6. (b) Monod, J.; Wyman, J.; Changeux, J.-P. J. Mol. Biol. 1965, 12, 88.
7. (a) Ackers, G. K.; Doyle, M. L.; Myers, D.; Daugherty, M. A. Science 1992, 255, 54.
8. (b) Huang, Y.; Doyle, M. L.; Ackers, G. K. Biophys. J. 1996, 71, 2094.
9. (c) Johnson, M. L. Methods Enzymol. 2000, 323, 124.
10. (a) Tabushi, I. Pure Appl. Chem. 1988, 60, 581.
11. (b) Takeuchi, M.; Imada, T.; Shinkai, S. J. Am. Chem. Soc. 1996, 118, 10658.
12. Elemans, J. A. A. W.; Claase, M. B.; Aarts, P. P. M.; Rowan, A. E.; Schenning, A. P. H. J.; Nolte, R. J. M. J. Org. Chem. 1999. 64, 7009.
13. (a) Selected experimental data for the synthesis of 6a are given in the Supporting Information; details for all of the compounds described here will be reported in a forthcoming paper.
14. 2h-symmetry.
15. (c) Because of the low yield of 6b. no binding studies have been carried out to date.
16. 3) showed that the symmetry of the host 6a breaks down as expected, although it should be noted that this could also be due to symmetry breaking that normally occurs when the inner imine-proton (NH) tautomerism is frozen out on the NMR time scale.
17. Rowan, A. E.; Aarts, P. P. M.; Koutstaal, K. W. M. Chem. Commun. 1998, 611.
18. This emission band is a result of excitation of the charge-transfer complex formed between the catechol-like cavity walls and the viologen guest. See also: Bernardo, A. R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1992, 114, 10624.
19. Wyman, J. Adv. Protein Chem. 1964, 18, 223.
20. Hyperchem 6.01, Hypercube Inc., Gainesville, FL, 2000.
21. Koshland, D. E., Jr.; Némethy, G.; Filmer. D. Biochemistry 1966, 5, 365.