Carboxylate Binding by 2-(Guanidiniocarbonyl)pyrrole Receptors in Aqueous Solvents: Improving the Binding Properties of Guanidinium Cations through Additional Hydrogen Bonds

Chemistry - A European Journal

Volumn 6, Issue 4, 2000, Pages 709-718

  Schmuck, Carsten ^a  

^a UNIVERSITY OF COLOGNE   (Germany)

Author keywords

Amino acids; Carboxylate receptors; Guanidinium cations; Molecular recognition; Supralecular chemistry

Indexed keywords

CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CELL SURFACE RECEPTOR; DRUG DERIVATIVE; GUANIDINE; GUANIDINE DERIVATIVE; PYRROLE DERIVATIVE; SOLVENT; WATER;

ARTICLE; BINDING SITE; CHEMISTRY; ENANTIOMER; ENZYME SPECIFICITY; HYDROGEN BOND; METABOLISM; MOLECULAR INTERACTION; MOLECULAR MIMICRY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THERMODYNAMICS;

BINDING SITES; CARBOXYLIC ACIDS; GUANIDINE; HYDROGEN BONDING; MOLECULAR MIMICRY; PYRROLES; RECEPTORS, CELL SURFACE; SOLVENTS; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THERMODYNAMICS; WATER;

EID: 0034681517     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000218)6:4<709::AID-CHEM709>3.0.CO;2-6     Document Type: Article

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10. For examples of peptide recognition in aqueous media see: a) A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11208-11209; b) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; c) M. Davies, M. Bonnat, F. Gullier, J. D. Kilburn, M. Bradley, J. Org. Chem. 1998, 63, 8696-8703; d) M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak, E. Giralt, J. Am. Chem. Soc. 1997, 119, 9327-9328; c) M. Maletic, H. Wennemers, D. Q. McDonald, R. Breslow, W. C. Still, Angew. Chem. 1996, 108, 1594-1596; Angew. Chem. Int. Ed. Engl. 1996, 35, 1490-1492; f) S. R. LaBrenz, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 1655-1656; g) J. S. Albert, M. S. Goodman, A. D. Hamilton, J. Am. Chem. Soc. 1995, 117, 1143-1144; h) H. Wennemers, W. C. Still, Tetrahedron Lett. 1994, 35, 6413-6416.
11. For examples of peptide recognition in aqueous media see: a) A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11208-11209; b) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; c) M. Davies, M. Bonnat, F. Gullier, J. D. Kilburn, M. Bradley, J. Org. Chem. 1998, 63, 8696-8703; d) M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak, E. Giralt, J. Am. Chem. Soc. 1997, 119, 9327-9328; c) M. Maletic, H. Wennemers, D. Q. McDonald, R. Breslow, W. C. Still, Angew. Chem. 1996, 108, 1594-1596; Angew. Chem. Int. Ed. Engl. 1996, 35, 1490-1492; f) S. R. LaBrenz, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 1655-1656; g) J. S. Albert, M. S. Goodman, A. D. Hamilton, J. Am. Chem. Soc. 1995, 117, 1143-1144; h) H. Wennemers, W. C. Still, Tetrahedron Lett. 1994, 35, 6413-6416.
12. For examples of peptide recognition in aqueous media see: a) A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11208-11209; b) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; c) M. Davies, M. Bonnat, F. Gullier, J. D. Kilburn, M. Bradley, J. Org. Chem. 1998, 63, 8696-8703; d) M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak, E. Giralt, J. Am. Chem. Soc. 1997, 119, 9327-9328; c) M. Maletic, H. Wennemers, D. Q. McDonald, R. Breslow, W. C. Still, Angew. Chem. 1996, 108, 1594-1596; Angew. Chem. Int. Ed. Engl. 1996, 35, 1490-1492; f) S. R. LaBrenz, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 1655-1656; g) J. S. Albert, M. S. Goodman, A. D. Hamilton, J. Am. Chem. Soc. 1995, 117, 1143-1144; h) H. Wennemers, W. C. Still, Tetrahedron Lett. 1994, 35, 6413-6416.
13. For examples of peptide recognition in aqueous media see: a) A. Hossain, H.-J. Schneider, J. Am. Chem. Soc. 1998, 120, 11208-11209; b) R. Breslow, Z. Yang, R. Ching, G. Trojandt, F. Odobel, J. Am. Chem. Soc. 1998, 120, 3536-3537; c) M. Davies, M. Bonnat, F. Gullier, J. D. Kilburn, M. Bradley, J. Org. Chem. 1998, 63, 8696-8703; d) M. W. Peczuh, A. D. Hamilton, J. Sanchez-Qesada, J. deMendoza, T. Haak, E. Giralt, J. Am. Chem. Soc. 1997, 119, 9327-9328; c) M. Maletic, H. Wennemers, D. Q. McDonald, R. Breslow, W. C. Still, Angew. Chem. 1996, 108, 1594-1596; Angew. Chem. Int. Ed. Engl. 1996, 35, 1490-1492; f) S. R. LaBrenz, J. W. Kelly, J. Am. Chem. Soc. 1995, 117, 1655-1656; g) J. S. Albert, M. S. Goodman, A. D. Hamilton, J. Am. Chem. Soc. 1995, 117, 1143-1144; h) H. Wennemers, W. C. Still, Tetrahedron Lett. 1994, 35, 6413-6416.
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