Side chain selective binding of N-acetyl-α-amino acid carboxylates by a 2-(guanidiniocarbonyl)pyrrole receptor in aqueous solvents
(Note: The full text of this document is currently only available in the PDF Version )
Carsten Schmuck
Abstract
2-(Guanidiniocarbonyl)pyrrole 1 binds N-acetyl-α-amino acid carboxylates in 40% H2O–DMSO with binding constants ranging from K = 360 to 1700 mol–1 depending on the structure of the amino acid side chain.
References
(a) J.-M. Lehn,
Supramolecular Chemistry; Concepts and Perspectives,
VCH,
Weinheim,
1995 Search PubMed; H. Dugas,
Bioorganic Chemistry, A Chemical Approach to Enzyme Action,
Springer Verlag,
New York,
1996 Search PubMedsee also
(b) W. C. Still, Acc. Chem. Res., 1996, 29, 155 CrossRefCAS.
(a) T. H. Webb and C. S. Wilcox, Chem. Soc. Rev., 1993, 383 RSC;
(b) see also Chem. Rev.,
1997,
97, vol 5, special issue ‘Molecular Recognition’ Search PubMed.
For examples of peptide recognition in aqueous media see: A. Hossain and H.-J. Schneider, J. Am. Chem. Soc., 1998, 120, 11208 Search PubMed; R. Breslow, Z. Yang, R. Ching, G. Trojandt and F. Odobel, J. Am. Chem. Soc., 1998, 120, 3536 CrossRefCAS; M. Davies, M. Bonnant, F. Guillier, J. D. Kilburn and M. Bradley, J. Org. Chem., 1998, 63, 8696 CrossRefCAS; M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak and E. Giralt, J. Am. Chem. Soc., 1997, 119, 9327 CrossRefCAS.
Recent review articles: F. P. Schmidtchen and M. Berger, Chem. Rev., 1997, 97, 1609 Search PubMed; A. Bianchi,
K. Bowman-James and
E. García-España,
Supramolecular Chemistry of Anions,
Wiley-VCH,
New York,
1997 CrossRefCAS; A. Galán and J. deMendoza, Top. Curr. Chem., 1995, 175 CrossRefCAS.
For a leading reference on general amino acid recognition, see: J. L. Sessler and A. Andrievsky, Chem. Eur. J., 1998, 4, 159 Search PubMed and references cited therein.
Side chain selective amino acid recognition in CDCl3: J. Dowden, P. D. Edwards and J. D. Kilburn, Tetrahedron Lett., 1997, 38, 1095 Search PubMed; C. P. Waymark, J. D. Kilburn and I. Gillies, Tetrahedron Lett., 1995, 36, 3051 CrossRefCAS; S. S. Flack and J. D. Kilburn, Tetrahedron Lett., 1995, 36, 3409 CrossRefCAS.
K. A. Connors,
Binding Constants,
Wiley,
New York,
1987 Search PubMed.
C. S. Wilcox, in
Frontiers in Supramolecular Chemistry and Photochemistry, ed.
H. J. Schneider and H. Dürr),
VCH,
Weinheim,
1990 Search PubMed.
In accordance with this scheme, in the 1H NMR spectrum one observes
downfield shifts of all those receptor NHs, which participate in the
proposed binding (up to 4 ppm in [2H6]DMSO). According to molecular
dynamics calculations, the receptor conformation necessary for this type
of binding is only 1 kJ mol–1 less stable than the energy minimum
conformation in water (compared to 14 kJ mol–1 in CHCl3).
T. H. Schrader, Tetrahedron Lett., 1998, 39, 517 CrossRefCAS; D. A. Dougherty, Science, 1996, 271, 163 CrossRefCAS and references cited therein.
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 CrossRefCAS.
Click here to see how this site uses Cookies. View our privacy policy here.