Diversity and selection in self-assembled tetrameric capsules [20]

Journal of the American Chemical Society

Volumn 122, Issue 17, 2000, Pages 4251-4252

  Hof, Fraser ^a   Nuckolls, Colin ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL STRUCTURE; LETTER; MASS SPECTROMETRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034600293     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0005136     Document Type: Letter

References (36)

1. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
2. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
3. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
4. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
5. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
6. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
7. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
8. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
9. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
10. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
11. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
12. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
13. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
14. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
15. Diversity achieved through the assembly of more than one type of molecular subunit: (a) Calama, M. C.; Timmerman, P.; Reinhoudt, D. N. Angew. Chem., Int. Ed. 2000, 39, 755. (b) Klekota, B.; Miller, B. L. Tetrahedron 1999, 55, 11687. (c) Huc, I.; Krische, M. J.; Funeriu, D. P.; Lehn, J.-M. Eur. J. Inorg. Chem. 1999, 1415. (d) Hioki, H.; Still, W. C. J. Org. Chem. 1998, 63, 904. (e) Rivera, J. M.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 819. (f) Castellano, R. K.; Kim, B. H.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 12671. (g) Klekota, B.; Hammond, M. H.; Miller, B. L. Tetrahedron Lett. 1997, 38, 8639. (h) Huc, I.; Lehn, J.-M. Proc. Nat. Acad. Sci. U.S.A. 1997, 94, 2106. Diversity achieved by the association of a single molecule into different assembled states: (i) Hiraoka, S.; Fujita, M. J. Am. Chem. Soc. 1999, 121, 10239. (j) Lee, S. B.; Hwang, S.; Chung, D. S.; Yun, H.; Hong, J.-I. Tetrahedron Lett. 1998, 39, 873. (k) Hasenknopf, B.; Lehn, J.-M.; Boumediene, N.; Dupont-Gervain, A.; Dorsselaer, A. V.; Kneisel, B.; Fenske, D. J. Am. Chem. Soc. 1997, 119, 10956. (l) Brady, P. A.; Sanders, J. K. M. J. Chem. Soc., Perkin Trans. 1 1997, 3237. For reviews and discussions: (m) Lehn, J.-M. Chem. Eur. J. 1999, 5, 2455. (n) Klekota, B.; Miller, B. L. Trends Biotech. 1999, 17, 205. (o) Ganesan, A. Angew. Chem., Int. Ed. 1998, 37, 2828.
16. Guest templation of receptors: (a) Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997, 119, 1147. (b) Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38, 1588. (c) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (d) Ibukoro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120, 8561.
17. Guest templation of receptors: (a) Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997, 119, 1147. (b) Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38, 1588. (c) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (d) Ibukoro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120, 8561.
18. Guest templation of receptors: (a) Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997, 119, 1147. (b) Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38, 1588. (c) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (d) Ibukoro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120, 8561.
19. Guest templation of receptors: (a) Eliseev, A. V.; Nelen, M. I. J. Am. Chem. Soc. 1997, 119, 1147. (b) Scherer, M.; Caulder, D. L.; Johnson, D. W.; Raymond, K. N. Angew. Chem., Int. Ed. 1999, 38, 1588. (c) Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649. (d) Ibukoro, F.; Kusukawa, T.; Fujita, M. J. Am. Chem. Soc. 1998, 120, 8561.
20. (a) Conn, M. M.; Rebek, J., Jr. Chem. Rev. 1997, 97, 1647.
21. (b) Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278.
22. Martín, T.; Obst, U.; Rebek, J., Jr. Science, 1998, 281, 1842.
23. Nuckolls, C.; Hof, F.; Martín, T.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 10281.
24. 5
25. For the use of ESMS to study the parent tetrameric capsule, see (a) Schalley, C. A.; Martín, T.; Obst, U.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 2133. (b) For application to other self-assembled systems, see: Schalley, C. A. Int. J. Mass. Spec. 2000, 194, 11 and references therein.
26. For the use of ESMS to study the parent tetrameric capsule, see (a) Schalley, C. A.; Martín, T.; Obst, U.; Rebek, J., Jr. J. Am. Chem. Soc. 1999, 121, 2133. (b) For application to other self-assembled systems, see: Schalley, C. A. Int. J. Mass. Spec. 2000, 194, 11 and references therein.
27. All cationic guests were added as the tetrafluoroborate salts.
28. It is impossible to measure the distribution of capsules formed in the absence of a guest's thermodynamic bias, due to the inability of the capsules to form without a guest. Thus, comparison to the mixture predicted by statistics is the only means of examining the thermodynamic bias imparted by the guests.
29. Molecular modeling of assemblies was carried out using MacroModel 6.5 and the Amber* force field: Mohamadi, F.; Richards, N. G. J.; Guide, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. Cavity volumes of minimized structures were calculated with the GRASP program: Nicholls, A.; Sharp, K. A.; Honig, B. Proteins 1991, 11, 281.
30. Molecular modeling of assemblies was carried out using MacroModel 6.5 and the Amber* force field: Mohamadi, F.; Richards, N. G. J.; Guide, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440. Cavity volumes of minimized structures were calculated with the GRASP program: Nicholls, A.; Sharp, K. A.; Honig, B. Proteins 1991, 11, 281.
31. The high occupancy factor (70-80%) is explained by attractive interactions between the capsule and the charged guests. See ref 7a and Mecozzi, S.; Rebek, J., Jr. Chem. Eur. J. 1998, 4, 1016.
32. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
33. (b) Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2288.
34. (c) Carell, T.; Wintner, E. A.; Sutherland, A. J.; Rebek, J., Jr.; Dunayevskiy, Y. M.; Vouros, P. Chem. Biol. 1995, 2, 171 and references therein.
35. 7a and the agreement observed between ESMS and NMR measurements.
36. The response of the detector varies as the inverse of the square root of the mass. For this library, (∼2700-3700), the mass discrimination is expected to result in a decrease in signal intensity of ∼15% for the heaviest species relative to the lightest. Over the smaller mass range of the libraries in Figure 2a, b these effects can be ignored.