Side chain selective binding of N-acetyl-α-amino acid carboxylates by a 2-(guanidiniocarbonyl)pyrrole receptor in aqueous solvents

Chemical Communications

Volumn , Issue 9, 1999, Pages 843-844

  Schmuck, Garsten ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; CARBOXYLIC ACID DERIVATIVE; PYRROLE DERIVATIVE; RECEPTOR; SOLVENT;

ARTICLE; BINDING AFFINITY;

EID: 0033532247     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a901126i     Document Type: Article

References (22)

1. (a) J.-M. Lehn, Supramolecular Chemistry; Concepts and Perspectives, VCH, Weinheim 1995;
2. H. Dugas, Bioorganic Chemistry, A Chemical Approach to Enzyme Action, Springer Verlag, New York, 1996;
3. see also (b) W. C. Still, Acc. Chem. Res., 1996, 29, 155.
4. (a) T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 383;
5. see also (b) Chem. Rev., 1997, 97, vol 5, special issue 'Molecular Recognition'.
6. For examples of peptide recognition in aqueous media see: A. Hossain, and H.-J. Schneider, J. Am. Chem. Soc., 1998, 120, 11 208;
7. R. Breslow, Z. Yang, R. Ching, G. Trojandt and F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536;
8. M. Davies, M. Bonnant, F. Guillier, J. D. Kilburn and M. Bradley, J. Org. Chem., 1998, 63, 8696;
9. M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak and E. Giralt, J. Am. Chem. Soc., 1997, 119, 9327.
10. Recent review articles: F. P. Schmidtchen, M. Berger, Chem. Rev., 1997, 97, 1609;
11. A. Bianchi, K. Bowman-James and E. García-España, Supramolecular Chemistry of Anions, Wiley-VCH, New York, 1997;
12. A. Galán and J. deMendoza, Top. Curr. Chem. 1995, 175.
13. For a leading reference on general amino acid recognition, see: J. L. Sessler and A. Andrievsky, Chem. Eur. J., 1998, 4, 159 and references cited therein.
14. 3: J. Dowden, P. D. Edwards and J. D. Kilburn, Tetrahedron Lett., 1997, 38, 1095;
15. C. P. Waymark, J. D. Kilburn and I. Gillies, Tetrahedron Lett., 1995, 36, 3051;
16. S. S. Flack and J. D. Kilburn, Tetrahedron Lett., 1995, 36, 3409.
17. K. A. Connors, Binding Constants, Wiley, New York, 1987.
18. C. S. Wilcox, in Frontiers in Supramolecular Chemistry and Photochemistry, ed. H. J. Schneider and H. Dürr), VCH, Weinheim, 1990.
19. 3).
20. T. H. Schrader, Tetrahedron Lett., 1998, 39, 517;
21. D. A. Dougherty, Science, 1996, 271, 163 and references cited therein.
22. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufiled, G. Chang, T. Hendrickson and W. C. Still, J. Comput. Chem., 1990, 11, 440.