Anion recognition by alkyl cholates: Neutral anionophores closely related to a natural product

Tetrahedron Letters

Volumn 39, Issue 25, 1998, Pages 4569-4572

  Davis, Anthony P ^a   Perry, Justin J ^a   Wareham, Richard S ^a  

^a TRINITY COLLEGE DUBLIN   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; CHOLIC ACID DERIVATIVE; IONOPHORE; NATURAL PRODUCT;

ARTICLE; HYDROGEN BOND; MEASUREMENT; MOLECULAR RECOGNITION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLUBILIZATION;

EID: 0032543516     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00808-9     Document Type: Article

References (29)

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2. 1. Haslewood, G. A. D. The Biological Importance of Bile Salts; North-Holland: Amsterdam, 1978. Sterols and Bile Acids; Danielsson, H., Sjövall, J., Eds.; Elsevier: Amsterdam, 1985.
3. 2. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257. Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283. Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev. 1997, 97, 1567.
4. 2. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257. Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283. Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev. 1997, 97, 1567.
5. 2. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257. Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283. Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev. 1997, 97, 1567.
6. 2. Leading refs.: Davis, A. P. Chem. Soc. Rev. 1993, 22, 243. Davis, A. P.; Bonar-Law, R. P.; Sanders, J. K. M. Comprehensive Supramolecular Chemistry; Murakami, Y., Ed.; Pergamon: Oxford, 1996; Vol. 4, p 257. Li, Y. X.; Dias, J. R. Chem. Rev. 1997, 97, 283. Walliman, P.; Marti, T.; Furer, A.; Diederich, F. Chem. Rev. 1997, 97, 1567.
7. 3. (a) Davis, A. P.; Gilmer, J. F.; Perry, J. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 1312,
8. (b) Davis, A. P.; Perry, J. J.; Williams, R. P. J. Am. Chem. Soc. 1997, 119, 1793.
9. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
10. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
11. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
12. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
13. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
14. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
15. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
16. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
17. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
18. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
19. 4. For general discussions of anion recognition see: Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609; Dietrich, B. Pure and Appl. Chem. 1993, 65, 1457. For examples of neutral organic anionophores from other laboratories, see: Valiyaveettil, S.; Engbersen, J. F. J.; Verboom, W.; Reinhoudt, D. N. Angew. Chem., Int. Ed. Engl. 1993, 32, 900. Morzherin, Y.; Rudkevich, D. M.; Verboom, W.; Reinhoudt, D. N. J. Org. Chem. 1993, 58, 7602. Raposo, C.; Pérez, N.; Almaraz, M.; Mussons, M. L.; Caballero, M. C.; Morán, J. R. Tetrahedron Lett. 1995, 36, 3255. Ishida, H.; Suga, M.; Donowaki, K.; Ohkubo, K. J. Org. Chem. 1995, 60, 5374. Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621. Gale, P. A.; Sessler, J. L.; Král, V.; Lynch, V. J. Am. Chem. Soc. 1996, 118, 5140. Berger, M.; Schmidtchen, F. P. J. Am. Chem. Soc. 1996, 118, 8947. Kavallieratos, K.; deGala, S. R.; Austin, D. J.; Crabtree, R. H. J. Am. Chem. Soc. 1997,119, 2325. Buhlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647.
20. 3-symmetrical) structures for the anion.
21. 6. Guest concentrations in the range 0 - 24 mM.
22. 7. Connors, K. A. Binding Constants; Wiley: New York, 1987, pp. 24-28.
23. 8. Wilcox, C. S. Frontiers in Supramolecular Chemistry and Photochemistry; Schneider, H.-J. and Durr, H., Eds.; VCH: Weinheim, 1990, p 123. Version 5.0 was used for the present work.
24. 9. The error analysis in HOSTEST gave a standard deviation of 56 for the 1:1 binding constant. In view of the modest fit and the low value for the second binding constant, use of the 1:1 + 2:1 binding model must be seen as tentative. The intrusion of other stoichiometries can certainly not be excluded.
25. 10. Prepared from cholic acid and octanol under catalysis by cone. HCl aq.
26. 11. Synthesized by hydrolysis of the corresponding triformate: see Carlson, G. L.; Belobaba, D. T. E.; Hofmann, A. F.; Wedmid, Y. Steroids 1977, 30, 787.
27. 2 has appreciable solubility. In parallel experiments, 8 and 2 were both accompanied by 1.2 equivalents of phenylphosphonate after filtration.
28. 13. Bonar-Law, R. P.; Davis, A. P. Tetrahedron 1993, 49, 9845.
29. 14. Waterhous, D. V.; Barnes, S.; Muccio, D. D. Journal of Lipid Research 1985, 26, 1068.