Molecular Tweezers and Clips as Synthetic Receptors. Molecular Recognition and Dynamics in Receptor-Substrate Complexes

Accounts of Chemical Research

Volumn 36, Issue 12, 2003, Pages 919-932

  Klärner, Frank Gerrit ^a   Kahlert, Björn ^a  

^a UNIVERSITY OF DUISBURG ESSEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE DERIVATIVE; NAPHTHALENE DERIVATIVE; NICOTINIC ACID METHYL ESTER; PYRIDINIUM DERIVATIVE;

AQUEOUS SOLUTION; BINDING KINETICS; CALCULATION; CHEMICAL BOND; CHEMICAL INTERACTION; COMPLEX FORMATION; DIELS ALDER REACTION; DISSOCIATION CONSTANT; ELECTRICITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHOBICITY; MOLECULAR DYNAMICS; MOLECULAR MECHANICS; MOLECULAR RECOGNITION; MOLECULAR STABILITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHASE TRANSITION; REACTION OPTIMIZATION; RECEPTOR BINDING; REVIEW; TEMPERATURE DEPENDENCE; THERMODYNAMICS;

BENZENE; BENZENE DERIVATIVES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; KINETICS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; NAPHTHALENES; SOLUTIONS; SOLVENTS; STEREOISOMERISM; TEMPERATURE; THERMODYNAMICS;

EID: 17944388214     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar0200448     Document Type: Review

References (51)

1. Lehn, J. M. Supramolecular Chemistry. Concepts and Perspectives; VCH: Weinheim, 1995.
2. Prins, L. J.; Reinhoudt, D. N.; Timmerman, P. Noncovalent synthesis using hydrogen bonding. Angew. Chem., Int. Ed. 2001, 40, 2383-2426.
3. Gallivan, J. P.; Dougherty, D. A. A computational study of cation-π interactions vs. salt bridges in aqueous media: Implications for protein engineering. J. Am. Chem. Soc. 2000, 122, 870-874.
4. Meyer, E. A.; Castellano, R. K.; Diederich, F. Interactions with Aromatic Rings in Chemical and Biological Recognition. Angew. Chem., Int. Ed. 2003, 42, 1210-1250.
5. Hunter, C. A.; Lawson, K. R.; Perkins, J.; Urch, C. J. Aromatic interactions. J. Chem. Soc., Perkin Trans. 2 2001, 651-669.
6. Sinnokrot, M. O.; Valeev, E. F.; Sherrill, C. D. Estimates of the ab initio limit for π-π interactions: The benzene dimer. J. Am. Chem. Soc. 2002, 124, 10887-10893.
7. Kim, E.; Paliwal, S.; Wilcox, C. S. Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition. J. Am. Chem. Soc. 1998, 120, 11192-11193. Nakamura, K.; Houk, K. N. Theoretical studies of the Wilcox molecular torsion balance. Is the edge-to-face aromatic interaction important? Org. Lett. 1999, 1, 2049-2051.
8. Kim, E.; Paliwal, S.; Wilcox, C. S. Measurements of molecular electrostatic field effects in edge-to-face aromatic interactions and CH-π interactions with implications for protein folding and molecular recognition. J. Am. Chem. Soc. 1998, 120, 11192-11193. Nakamura, K.; Houk, K. N. Theoretical studies of the Wilcox molecular torsion balance. Is the edge-to-face aromatic interaction important? Org. Lett. 1999, 1, 2049-2051.
9. Lehn, J. M. Mechanistic features, cooperativity, and robustness in the self-assembly of multicomponent silver(I) grid-type metalloarchitectures. Angew. Chem., Int. Ed. 2002, 41, 3738-3738. Seidel, S. R.; Stang, P. J. High-symmetry coordination cages via self-assembly. Acc. Chem. Res. 2002, 35, 972-983.
10. Lehn, J. M. Mechanistic features, cooperativity, and robustness in the self-assembly of multicomponent silver(I) grid-type metalloarchitectures. Angew. Chem., Int. Ed. 2002, 41, 3738-3738. Seidel, S. R.; Stang, P. J. High-symmetry coordination cages via self-assembly. Acc. Chem. Res. 2002, 35, 972-983.
11. Rekharsky, M. V.; Inoue, Y. Complexation thermodynamics of cyclodextrins. Chem. Rev. 1998, 98, 1875-1917.
12. Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
13. Ma, J. C.; Dougherty, D. A. The cation-π interaction. Chem. Rev. 1997, 97, 1303-1324.
14. Philp, D.; Stoddart, J. F. Self-assembly in natural and unnatural systems. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155-1196.
15. Cram, D. J. Container Molelcules and their Guests; Royal Society of Chemistry: Cambridge, 1994. Warmuth, R.; Yoon, J. Recent highlights in hemicarcerand chemistry. Acc. Chem. Res. 2001, 34, 95-105.
16. Cram, D. J. Container Molelcules and their Guests; Royal Society of Chemistry: Cambridge, 1994. Warmuth, R.; Yoon, J. Recent highlights in hemicarcerand chemistry. Acc. Chem. Res. 2001, 34, 95-105.
17. Collet, A.; Dutasta, J. P.; Lozach, B.; Canceill, J. Cyclotriveratrylenes and Cryptophanes - Their Synthesis and Applications to Host-Guest Chemistry and to the Design of New Materials. Top. Curr. Chem. 1993, 165, 103-129.
18. Lee, J. W.; Samal, S.; Selvapalam, N.; Kim, H.-J.; Kim, K. Cucurbituril Homologues and Derivatives: New Opportunities in Supramolekular Chemistry. Acc. Chem. Res. 2003, 36, 621-630.
19. Hof, F.; Craig, S. L.; Nuckolls, C.; Rebek, J. Molecular encapsulation. Angew. Chem., Int. Ed. 2002, 41, 1488-1508.
20. Chen, C.-W.; Whitlock, H. W. Molecular Tweezers: A Simple Model of Bifunctional Intercalation. J. Am. Chem. Soc. 1978, 100, 4921-4922. Zimmerman, S. C.; VanZyl, C. M. Rigid Molecular Tweezers: Synthesis, Characterization, and Complexation Chemistry of a Diacridine. J. Am. Chem. Soc. 1987, 109, 7894-7896. Zimmerman, S. C.; Saionz, K. W. Quantitative Host-Guest Complexation Studies Using Chemically Bonded Stationary Phases - a Comparison of Hplc and Solution Enthalpies. J. Am. Chem. Soc. 1995, 117, 1175-1176. Fleischhauer, J.; Harmata, M.; Kahraman, M.; Koslowski, A.; Welch, C. J. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett. 1997, 38, 8655-8658. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution. Tetrahedron 2001, 57, 8667-8674.
21. Chen, C.-W.; Whitlock, H. W. Molecular Tweezers: A Simple Model of Bifunctional Intercalation. J. Am. Chem. Soc. 1978, 100, 4921-4922. Zimmerman, S. C.; VanZyl, C. M. Rigid Molecular Tweezers: Synthesis, Characterization, and Complexation Chemistry of a Diacridine. J. Am. Chem. Soc. 1987, 109, 7894-7896. Zimmerman, S. C.; Saionz, K. W. Quantitative Host-Guest Complexation Studies Using Chemically Bonded Stationary Phases - a Comparison of Hplc and Solution Enthalpies. J. Am. Chem. Soc. 1995, 117, 1175-1176. Fleischhauer, J.; Harmata, M.; Kahraman, M.; Koslowski, A.; Welch, C. J. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett. 1997, 38, 8655-8658. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution. Tetrahedron 2001, 57, 8667-8674.
22. Chen, C.-W.; Whitlock, H. W. Molecular Tweezers: A Simple Model of Bifunctional Intercalation. J. Am. Chem. Soc. 1978, 100, 4921-4922. Zimmerman, S. C.; VanZyl, C. M. Rigid Molecular Tweezers: Synthesis, Characterization, and Complexation Chemistry of a Diacridine. J. Am. Chem. Soc. 1987, 109, 7894-7896. Zimmerman, S. C.; Saionz, K. W. Quantitative Host-Guest Complexation Studies Using Chemically Bonded Stationary Phases - a Comparison of Hplc and Solution Enthalpies. J. Am. Chem. Soc. 1995, 117, 1175-1176. Fleischhauer, J.; Harmata, M.; Kahraman, M.; Koslowski, A.; Welch, C. J. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett. 1997, 38, 8655-8658. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution. Tetrahedron 2001, 57, 8667-8674.
23. Chen, C.-W.; Whitlock, H. W. Molecular Tweezers: A Simple Model of Bifunctional Intercalation. J. Am. Chem. Soc. 1978, 100, 4921-4922. Zimmerman, S. C.; VanZyl, C. M. Rigid Molecular Tweezers: Synthesis, Characterization, and Complexation Chemistry of a Diacridine. J. Am. Chem. Soc. 1987, 109, 7894-7896. Zimmerman, S. C.; Saionz, K. W. Quantitative Host-Guest Complexation Studies Using Chemically Bonded Stationary Phases - a Comparison of Hplc and Solution Enthalpies. J. Am. Chem. Soc. 1995, 117, 1175-1176. Fleischhauer, J.; Harmata, M.; Kahraman, M.; Koslowski, A.; Welch, C. J. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett. 1997, 38, 8655-8658. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution. Tetrahedron 2001, 57, 8667-8674.
24. Chen, C.-W.; Whitlock, H. W. Molecular Tweezers: A Simple Model of Bifunctional Intercalation. J. Am. Chem. Soc. 1978, 100, 4921-4922. Zimmerman, S. C.; VanZyl, C. M. Rigid Molecular Tweezers: Synthesis, Characterization, and Complexation Chemistry of a Diacridine. J. Am. Chem. Soc. 1987, 109, 7894-7896. Zimmerman, S. C.; Saionz, K. W. Quantitative Host-Guest Complexation Studies Using Chemically Bonded Stationary Phases - a Comparison of Hplc and Solution Enthalpies. J. Am. Chem. Soc. 1995, 117, 1175-1176. Fleischhauer, J.; Harmata, M.; Kahraman, M.; Koslowski, A.; Welch, C. J. The determination of the absolute configuration of a chiral molecular tweezer using CD spectroscopy. Tetrahedron Lett. 1997, 38, 8655-8658. Kurebayashi, H.; Haino, T.; Usui, S.; Fukazawa, Y. Structure of supramolecular complex of flexible molecular tweezers and planar guest in solution. Tetrahedron 2001, 57, 8667-8674.
25. Rowan, A. E.; Elemans, J. A. A. W.; Nolte, R. J. M. Molecular and Supramolecular Objects from Glycoluril. Acc. Chem. Res. 1999, 32, 995-1006.
26. Burley, S. K.; Petsko, G. A. Aromatic-Aromatic Interaction: A Mechanism of Protein Structure Stabilization. Science 1985, 229, 23-28.
27. Cox, E. G.; Cruickshank, D. W. J.; Smith, J. A. S. The crystal structure of benzene at -3 °C. Proc. R. Soc. London A 1958, 247, 1-21.
28. Cozzi, F.; Cinquini, M.; Annuziata, R.; Siegel, J. S. Dominance of Polar/Pi over Charge-Transfer Effects in Stacked Phenyl Interactions. J. Am. Chem. Soc. 1993, 115, 5330-5331.
29. Zimmerman, S. C.; Corbin, F. S. Heteroaromatic modules for self-assembly using multiple hydrogen bonds. Struct. Bonding 2000, 96, 63-94.
30. Klärner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Molecular tweezers as synthetic receptors in host-guest chemistry: Inclusion of cyclohexane and self-assembly of aliphatic side chains. Angew. Chem., Int. Ed. Engl. 1996, 35, 1130-1133. Benkhoff, J.; Boese, R.; Klärner, F.-G. Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive DielsAlder reactions. Liebigs Ann. Recl. 1997, 501-516. Klärner, F.-G.; Lobert, M.; Naatz, U.; Bandmann, H.; Boese, R. Synthesis and Supramolecular Properties of Trimethylene-Bridged Clips. Chem. Eur. J. 2003, 9, 5036-5047.
31. Klärner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Molecular tweezers as synthetic receptors in host-guest chemistry: Inclusion of cyclohexane and self-assembly of aliphatic side chains. Angew. Chem., Int. Ed. Engl. 1996, 35, 1130-1133. Benkhoff, J.; Boese, R.; Klärner, F.-G. Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive DielsAlder reactions. Liebigs Ann. Recl. 1997, 501-516. Klärner, F.-G.; Lobert, M.; Naatz, U.; Bandmann, H.; Boese, R. Synthesis and Supramolecular Properties of Trimethylene-Bridged Clips. Chem. Eur. J. 2003, 9, 5036-5047.
32. Klärner, F.-G.; Benkhoff, J.; Boese, R.; Burkert, U.; Kamieth, M.; Naatz, U. Molecular tweezers as synthetic receptors in host-guest chemistry: Inclusion of cyclohexane and self-assembly of aliphatic side chains. Angew. Chem., Int. Ed. Engl. 1996, 35, 1130-1133. Benkhoff, J.; Boese, R.; Klärner, F.-G. Synthesis of sterically rigid macrocycles by the use of pressure-induced repetitive DielsAlder reactions. Liebigs Ann. Recl. 1997, 501-516. Klärner, F.-G.; Lobert, M.; Naatz, U.; Bandmann, H.; Boese, R. Synthesis and Supramolecular Properties of Trimethylene-Bridged Clips. Chem. Eur. J. 2003, 9, 5036-5047.
33. Klärner, F.-G.; Burkert, U.; Kamieth, M.; Boese, R.; Benet-Buchholz, J. Molecular tweezers as synthetic receptors: Molecular recognition of electron-deficient aromatic and aliphatic substrates. Chem. Eur. J. 1999, 5, 1700-1707.
34. Klärner, F.-G.; Panitzky, J.; Bläser, D.; Boese, R. Synthesis and supramolecular structures of molecular clips. Tetrahedron 2001, 57, 3673-3687.
35. Klärner, F.-G.; Burkert, U.; Kamieth, M.; Boese, R. Molecular tweezers as synthetic receptors: molecular recognition of neutral and cationic aromatic substrates. A comparison between the supramolecular structures in crystal and in solution. J. Phys. Org. Chem. 2000, 13, 604-611.
36. Ruloff, R.; Seelbach, U. P.; Merbach, A. E.; Klärner, F.-G. Molecular tweezers as synthetic receptors: the effect of pressure and temperature on the formation of host-guest complexes. J. Phys. Org. Chem. 2002, 15, 189-196. Ruloff, R.; Saudan, C.; Merbach, A. E.; Klärner, F.-G. Future Perspectives: Application of High Pressure in Supramolecular Chemistry. In High-Pressure Chemistry: Synthetic, Mechanistic, and Supercritical Applications; van Eldik, R., Klärner, F.-G., Eds.; Wiley-VCH: Weinheim, 2002; pp 348-368.
37. Ruloff, R.; Seelbach, U. P.; Merbach, A. E.; Klärner, F.-G. Molecular tweezers as synthetic receptors: the effect of pressure and temperature on the formation of host-guest complexes. J. Phys. Org. Chem. 2002, 15, 189-196. Ruloff, R.; Saudan, C.; Merbach, A. E.; Klärner, F.-G. Future Perspectives: Application of High Pressure in Supramolecular Chemistry. In High-Pressure Chemistry: Synthetic, Mechanistic, and Supercritical Applications; van Eldik, R., Klärner, F.-G., Eds.; Wiley-VCH: Weinheim, 2002; pp 348-368.
38. Klärner, F.-G.; Kahlert, B., unpublished results.
39. Halgren, T. A. Merck molecular force field. 1. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519. Spartan '02, v. 1.0.2; Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612.
40. Halgren, T. A. Merck molecular force field. 1. Basis, form, scope, parameterization, and performance of MMFF94. J. Comput. Chem. 1996, 17, 490-519. Spartan '02, v. 1.0.2; Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612.
41. Brown, S. P.; Schaller, T.; Seelbach, U. P.; Koziol, F.; Ochsenfeld, C.; Klärner, F.-G.; Spiess, H. W. Structure and dynamics of the host-guest complex of a molecular tweezer: Coupling synthesis, solid-state NMR, and quantum-chemical calculations. Angew. Chem., Int. Ed. 2001, 40, 717-720.
42. Ochsenfeld, C.; Koziol, F.; Brown, S. P.; Schaller, T.; Seelbach, U. P.; Klärner, F.-G. A study of a molecular tweezer Host-Guest system by a combination of quantum-chemical calculations and solid-state NMR experiments. Solid State Nucl. Magn. Reson. 2002, 22, 128-153.
43. Klärner, F.-G.; Bandmann, H.; Burkert, U.; Lobert, M.; Podsadlowski, V.; Seelbach, U. P., unpublished results.
44. Kamieth, M.; Burkert, U.; Corbin, P. S.; Dell, S. J.; Zimmerman, S. C.; Klärner, F.-G. Molecular tweezers as synthetic receptors: Molecular recognition of electron-deficient aromatic substrates by chemically bonded stationary phases. Eur. J. Org. Chem. 1999, 2741-2749.
45. Jasper, C.; Schrader, T.; Panitzky, J.; Klärner, F.-G. Selective complexation of N-alkylpyridinium salts: Recognition of NAD-(+) in water. Angew. Chem., Int. Ed. 2002, 41, 1355-1358.
46. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. Macro-Mode - An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467. Macromodel, v. 7.0; Schrödinger, Inc., 1500 SW First Ave., Ste. 1180, Portland, OR 97201.
47. Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. Macro-Mode - An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467. Macromodel, v. 7.0; Schrödinger, Inc., 1500 SW First Ave., Ste. 1180, Portland, OR 97201.
48. Kamieth, M.; Klärner, F.-G.; Diederich, F. Modeling the supramolecular properties of aliphatic-aromatic hydrocarbons with convex-concave topology. Angew. Chem., Int. Ed. 1998, 37, 3303-3306. Klärner, F.-G.; Panitzky, J.; Preda, D.; Scott, L. T. Modeling of supramolecular properties of molecular tweezers, clips, and bowls. J. Mol. Model. 2000, 6, 318-327.
49. Kamieth, M.; Klärner, F.-G.; Diederich, F. Modeling the supramolecular properties of aliphatic-aromatic hydrocarbons with convex-concave topology. Angew. Chem., Int. Ed. 1998, 37, 3303-3306. Klärner, F.-G.; Panitzky, J.; Preda, D.; Scott, L. T. Modeling of supramolecular properties of molecular tweezers, clips, and bowls. J. Mol. Model. 2000, 6, 318-327.
50. Denti, T. Z. M.; van Gunsteren, W. F.; Diederich, F. Computer simulations of the solvent dependence of apolar association strength: Gibbs free energy calculations on a cyclophane-pyrene complex in water and chloroform. J. Am. Chem. Soc. 1996, 118, 6044-6051.
51. Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. Molecular Recognition in Aqueous-Media-New Binding-Studies Provide Further Insights into the Cation-Pi Interaction and Related Phenomena. J. Am. Chem. Soc. 1993, 115, 9907-9919.