Design, Synthesis, and Self-Assembly of "Artificial Dinucleotide Duplexes"

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4079-4091

  Sessler, Jonathan L ^a   Wang, Ruizheng ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001576240     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980194p     Document Type: Article

References (53)

1. (a) Sessler, J. L.; Magda, D. J.; Hugdahl, J. J. Incl. Phenomen. 1989, 7, 19.
2. (b) Sessler, J. L.; Magda, D. In Inclusion Phenomena and Molecular Recognition; Atwood, J. L., Ed., Plenum Press: New York, 1989; p 17.
3. (c) Sessler, J. L.; Magda, D.; Furuta, H. J. Org. Chem. 1992, 57, 818.
4. For recent reviews on self-assembly, see: (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (b) Philp, D. S.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (d) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312. (e) Comprehensive Supramolecular Chemistry, Vol. 9; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Elsevier: Exeter, 1996)
5. For recent reviews on self-assembly, see: (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (b) Philp, D. S.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (d) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312. (e) Comprehensive Supramolecular Chemistry, Vol. 9; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Elsevier: Exeter, 1996)
6. For recent reviews on self-assembly, see: (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (b) Philp, D. S.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (d) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312. (e) Comprehensive Supramolecular Chemistry, Vol. 9; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Elsevier: Exeter, 1996)
7. For recent reviews on self-assembly, see: (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (b) Philp, D. S.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (d) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312. (e) Comprehensive Supramolecular Chemistry, Vol. 9; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Elsevier: Exeter, 1996)
8. For recent reviews on self-assembly, see: (a) Lawrence, D. S.; Jiang, T.; Levett, M. Chem. Rev. 1995, 95, 2229. (b) Philp, D. S.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1154. (c) Whitesides, G. M.; Simanek, E. E.; Mathias, J. P.; Seto, C. T.; Chin, D. N.; Mammen, M.; Gordon, D. M. Acc. Chem. Res. 1995, 28, 37. (d) Whitesides, G. M.; Mathias, J. P.; Seto, C. T. Science 1991, 254, 1312. (e) Comprehensive Supramolecular Chemistry, Vol. 9; Atwood, J. L., Davies, J. E. D., Macnicol, D. D., Vogtle, F., Eds.; Elsevier: Exeter, 1996)
9. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
10. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
11. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
12. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
13. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
14. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
15. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
16. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
17. For recent examples on self-assembly, see: (a) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095. (b) Kang, J.; Rebek, J., Jr. Nature 1996, 382, 239. (c) Grotzfeld, R. M.; Branda, N.; Rebek, J., Jr. Science 1996, 271, 487. (d) Sessler, J. L.; Andrievsky, A.; Gale, P. A.; Lynch, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 2782, (e) Hamann, B. C.; Shimizu, K. D.; Rebek, J., Jr. Angew. Chem., Int. Ed. Engl. 1996, 35, 1326. (f) Tirumala, S.; Davis, J. T. J. Am. Chem. Soc. 1997, 119, 2769. (g) Davis, J. T.; Tirumala, S. K.; Marlow, A. L. J. Am. Chem. Soc. 1997, 119, 5271. (h) Nakamura, K.; Sheu, C.; Keating, A. E.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 4321. (i) Meissner, R.; Garcias, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77.
18. (a) Schall, O. F.; Gokel, G. W. J. Am. Chem. Soc. 1994, 116, 6089,
19. (b) Schall, O. F.; Gokel, G. W. J. Chem. Soc., Chem. Commun. 1992, 748.
20. (c) Schall, O. F.; Robinson, K.; Atwood, J. L.; Gokel, G. W. J. Am. Chem. Soc. 1991, 113, 7434.
21. (d) Kim, M.; Gokel, G. W. J. Chem. Soc., Chem. Commun. 1987, 1686.
22. (e) Sessler, J. L.; Wang, B.; Harrimann, A. J. Am. Chem. Soc. 1995, 117, 704.
23. (f) Sessler, J. L.; Wang, B.; Harrimann, A. J. Am. Chem. Soc. 1993, 115, 10418.
24. (g) Harrimann, A.; Kubo, Y.; Sessler, J. L. J. Am. Chem. Soc. 1992, 114, 388.
25. (h) Kral, V.; Sessler, J. L. Tetrahedron 1995, 51, 539.
26. (a) Kyogoku, Y.; Lord, R. C.; Rich, A. Proc. Biochim. Biophys. Acta 1969, 179 10.
27. (b) Kyogoku, Y.; Lord, R. C.; Rich, A. Natl. Acad. Sci. U.S.A. 1967, 57, 250.
28. (a) Murry, T. J.; Zimmerman, S. C. J. Am. Chem. Soc. 1992, 114, 4010.
29. (b) Pranata, J.; Wierschke, S. O.; Jorgensen, W. L. J. Am. Chem. Soc. 1991, 113, 2810.
30. Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808.
31. Jorgensen, W. L.; Pranata, J. J. Am. Chem. Soc. 1990, 112, 2008.
32. Still, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 1228.
33. Schlosser, M., Ed. Organometallics in Synthesis; John Wiley & Sons: New York, 1994.
34. (a) Heck, R. F. Palladium Reagents in Organic Syntheses; Academic Press: London, 1985.
35. (b) Heck, R. F. Org. React. 1982, 27, 345.
36. (c) Sonogashira, K.; Hugihara, N. Tetrahedron Lett. 1975, 4467.
37. (a) House, H. O.; Koepsell, D.; Jaeger, W. J. Org. Chem. 1973, 38, 1167.
38. (b) House, H. O.; Hrabie, J. A.; vanDerree, D. J. Org. Chem. 1986, 51, 921.
39. Katz, H. E. J. Org. Chem. 1989, 54, 2179.
40. (a) For sugar protection, see: Matsuda, A. Synthesis 1986, 385.
41. (b) For iodonation of undines, see: Sy, W.-W. Synth. Commun. 1990, 20, 3391.
42. (c) For bromination of adenosine/guanosine, see: Holmes, R. E.; Robins, R. K. J. Am. Chem. Soc. 1964, 86, 1242.
43. Wang, B. Ph.D. Dissertation, The University of Texas at Austin, 1994.
44. Tsang, K. Y.; Diaz, H.; Graciani, N.; Kelly, J. W. J. Am. Chem. Soc. 1994, 116, 3988.
45. Logue, M. W.; Teng, K. J. Org. Chem. 1982, 47, 2549.
46. Sessler, J. L.; Brown, C. T.; Wang, R.; Hirose, T. Inorg. Chim. Acta 1996, 251, 135.
47. Davies, A. G.; Kleinschmidt, D. C.; Palan, P. R.; Vasishtha, S. C. J. Chem. Soc. (B) 1971, 3972.
48. Valdes, C.; Spitz, U. P.; Toledo, L.; Kubik, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1995, 117, 12733.
49. Iwahashi, H.; Kyogoku, Y. J. Am. Chem. Soc. 1977, 99, 7761.
50. 3.
51. (a) Connors, K. A. Binding Constants; John Wiley & Sons: New York, 1987.
52. (b) Feeney, J.; Batchelor, J. G.; Albrand, J. P.; Roberts, G. C. K. J. Magn. Reson. 1979, 33, 519.
53. -1 (see Supporting Information for details).