Deepening cavitands

European Journal of Organic Chemistry

Volumn , Issue 9, 1999, Pages 1991-2005

  Rudkevich, Dmitry M ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Cavitands; Encapsulation; Hydrogen bonding; Molecular recognition; Self assembly

Indexed keywords

CALIXARENE; RESORCINOL;

DRUG SYNTHESIS; ENCAPSULATION; HYDROGEN BOND; MOLECULAR RECOGNITION; PROTEIN ASSEMBLY; PROTEIN FOLDING; PROTON NUCLEAR MAGNETIC RESONANCE; SHORT SURVEY; SOLVATION; STRUCTURE ANALYSIS;

EID: 0032865784     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199909)1999:9<1991::aid-ejoc1991>3.0.co;2-5     Document Type: Short Survey

References (102)

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67. [29c] R. Yanagihara, M. Tominaga, Y. Aoyama, J. Org. Chem. 1994, 59, 6865-6867. A cyclic array of cooperative intramolecular hydrogen bonds is somewhat responsible for the structure of valinomycin, a natural ionophore, and its complexes with cations, see: M. Dobler, in: Comprehensive Supramolecular Chemistry, vol. 1 (Ed.: G. W. Gokel), Pergamon, 1996, p. 267-313. Peptide-functionalized calixarenes:
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71. [30b] D. M. Rudkevich, G. Hilmersson, J. Rebek, Jr. J. Am. Chem. Soc. 1998, 120, 12216-12225.
72. [30c] S. Ma, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem., in press.
73. An example in resorcinarene host-guest chemistry was reported by Aoyama et al.: [31a] Y. Kikuchi, Y. Kato, Y. Tanaka, H. Toi, Y. Aoyama, J. Am. Chem. Soc. 1991, 113, 1349-1354.
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83. [37b] J. de Mendoza, Chem. Eur. J. 1998, 4, 1373-1377. Reversible molecular capsules, based on tetrahydroxycavitands and their complexes were fully characterized both in solution and in solid state, see: R. G. Chapman, G. Olovsson, J. Trotter, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 6252-6260.
84. [37b] J. de Mendoza, Chem. Eur. J. 1998, 4, 1373-1377. Reversible molecular capsules, based on tetrahydroxycavitands and their complexes were fully characterized both in solution and in solid state, see: R. G. Chapman, G. Olovsson, J. Trotter, J. C. Sherman, J. Am. Chem. Soc. 1998, 120, 6252-6260.
85. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027; benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, J. Chem. Soc., Chem. Comm. 1998, 59-60. For a Diels-Alder reaction in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
86. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027; benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, J. Chem. Soc., Chem. Comm. 1998, 59-60. For a Diels-Alder reaction in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
87. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027; benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, J. Chem. Soc., Chem. Comm. 1998, 59-60. For a Diels-Alder reaction in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
88. Cyclobutadiene in covalently assembled carcerands: D. J. Cram, M. E. Tanner, R. Thomas, Angew. Chem. Int. Ed. Engl. 1991, 30, 1024-1027; benzyne: R. Warmuth, Angew. Chem. Int. Ed. Engl. 1997, 36, 1347-1350; R. Warmuth, J. Chem. Soc., Chem. Comm. 1998, 59-60. For a Diels-Alder reaction in a self-assembled capsule: J. Kang, J. Rebek, Jr., Nature 1997, 385, 50-52.
89. P. Jacopozzi, E. Dalcanale, Angew. Chem. Int. Ed. Engl. 1997, 36, 613-615.
90. O. D. Fox, N. K. Dalley, R. G. Harrison, J. Am. Chem. Soc. 1998, 120, 7111-7112.
91. Recent calculations of occupancy factors, or packing coefficients, of molecule-within-molecule complexes in solution indicate that an optimal value is about 55% occupancy. See: S. Mecozzi, J. Rebek, Jr., Chem. Eur. J. 1998, 4, 1016-1022.
92. [42a] O. Mogck, V. Böhmer, W. Vogt, Tetrahedron 1996, 52, 8489-8496.
93. [42b] J. Scheerder, J. P. M. van Duynhoven, J. F. J. Engbersen, D. N. Reinhoudt, Angew. Chem. Int. Ed. Engl. 1996, 35, 1090-1093.
94. [42c] R. K. Castellano, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1996, 118, 10002-10003.
95. T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Nature 1998, 394, 764-766.
96. M. H. K. Ebbing, M. J. Villa, J. M. Valpuesta, P. Prados, J. de Mendoza, presented at: Supramolecular Chemistry, European Research Conference, Rolduc, The Netherlands, September 1998. Also: B. Lammerink, D. M. Rudkevich, J. Rebek, Jr., unpublished observations.
97. M. H. K. Ebbing, M. J. Villa, J. M. Valpuesta, P. Prados, J. de Mendoza, presented at: Supramolecular Chemistry, European Research Conference, Rolduc, The Netherlands, September 1998. Also: B. Lammerink, D. M. Rudkevich, J. Rebek, Jr., unpublished observations.
98. T. Heinz, D. M. Rudkevich, J. Rebek, Jr., Angew. Chem. Int. Ed. Engl. 1999, 38, 1136-1139.
99. F. C. Tucci, D. M. Rudkevich, J. Rebek, Jr., J. Am. Chem. Soc. 1999, 121, 4928-4929.
100. + recorded by: K. Murayama, K. Aoki, Chem. Commun. 1998, 607-608. For a self-assembled dimeric resorcinarene capsule in an apolar solvent see: Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, Y. Aovama. J. Am. Chem. Soc. 1992, 114, 10302-10306.
101. + recorded by: K. Murayama, K. Aoki, Chem. Commun. 1998, 607-608. For a self-assembled dimeric resorcinarene capsule in an apolar solvent see: Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, Y. Aovama. J. Am. Chem. Soc. 1992, 114, 10302-10306.
102. + recorded by: K. Murayama, K. Aoki, Chem. Commun. 1998, 607-608. For a self-assembled dimeric resorcinarene capsule in an apolar solvent see: Y. Kikuchi, Y. Tanaka, S. Sutarto, K. Kobayashi, H. Toi, Y. Aovama. J. Am. Chem. Soc. 1992, 114, 10302-10306.