Large extra-cavity contributions to hydrophobic binding of lipophilic substrates in synthetic receptor models

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 3, 1990, Pages 276-278

  Schneider, Hans Jörg ^a   Kramer, Rüdiger ^a   Theis, Isolde ^a   Zhou, Mao Quing ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049072953     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39900000276     Document Type: Article

References (20)

1. K. Odashima and K. Koga, Cyclophanes, 629, Academic Press, New York.
2. H.-J. Schneider, K. Philippi and J. Pöhlmann, Angew. Chem., 96, 907.
3. H.-J. Schneider, K. Philippi and J. Pöhlmann, Angew Chem., Int. Ed. Engl., 23, 908.
4. H.-J. Schneider, R. Kramer, S. Simova and U. Schneider, J. Am. Chem. Soc., 110, 6442.
5. H.-J. Schneider and J. Pöhlmann, Bioorg. Chem., 15, 183.
6. M.A. Petti, T.J. Sheppod, R.E. BarransJr. and D.A. Dougherty, J. Am. Chem. Soc., 110, 6825.
7. H.-J. Schneider, Th. Blatter, S. Simova and I. Theis, J. Chem. Soc., Chem. Commun., 586.
8. S.K. Burley and G.A. Petsko, FEBS Lett., 203, 139.
9. B. Brooks, R. Bruccoleri, B. Olafson, D. States, S. Swaminathan and M. Karplus, J. Comp. Chem., 4, 187.
10. S. Kumar and H.-J. Schneider, J. Chem. Soc., Perkin Trans. 2, 245.
11. R. Struthers, A.T. Hagler and J. Rivier, Conformationally Directed Drug Design, 239, (simulation with Discover-Biosym program), cf. ACS, Washington, DC.
12. A.T. Hagler, The Peptides, V. J. Hruby, J. Meienhofer, Academic Press, New York.
13. K.A. Connors, Binding Constants, Wiley, New York.
14. F. Diederich, Angew. Chem., 100, 372, Large increases of binding energies with substrate size have been observed earlier, they were, however, attributed to a better complementarily to the cavities of the hosts used in these studies.
15. F. Diederich, Angew. Chem., Int. Ed. Engl., 27, 362, The better binding of ANS (6) in azoniacyclophanes of type CP66 in comparison to naphthalene sulphonates has been noted earlier, however without NMR–CIS values or any explanations, see ref 1.
16. W.L. Jorgensen, Acc. Chem. Res., 22, 184.
17. P.D.J. Grootenhuis and P.A. Kollmann, J. Am. Chem. Soc., 111, 4046.
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