Chemical Selection and Self-Assembly in a Cyclization Reaction

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 8, 1997, Pages 846-848

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

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Hydrogen bonds; Self assembly; Supramolecular chemistry; Template synthesis

Indexed keywords

EID: 0030916483     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199708461     Document Type: Article

References (34)

1. For timely reviews on self-assembly see: G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319; D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
2. For timely reviews on self-assembly see: G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319; D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
3. For timely reviews on self-assembly see: G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319; D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
4. For timely reviews on self-assembly see: G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319; D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260; D. Philp, J. F. Stoddart, Angew. Chem. 1996, 108, 1242-1286; Angew. Chem. Int. Ed. Engl. 1996, 35, 1154-1196.
5. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
6. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
7. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
8. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
9. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
10. N. Branda, R. Wyler, J. Rebek, Jr., Science 1994, 263, 1267-1268; R. S. Meissner, J. Rebek, Jr., J. de Mendoza, ibid. 1995, 270, 1485-11488; R. M. Grotzfeld, N. Branda, J. Rebek, Jr., ibid. 1996, 271, 487-489; B. C. Hamann, K. D. Shimizu, J. Rebek, Jr., Angew. Chem. 1996, 108, 1425-1427; Angew. Chem. Int. Ed. Engl. 1996, 35, 1326-1329; J. Kang, J. Rebek, Jr., Nature 1996, 382, 239-241.
11. For reviews on template effects see: S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475; R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384; D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
12. For reviews on template effects see: S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475; R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384; D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
13. For reviews on template effects see: S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475; R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384; D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
14. For reviews on template effects see: S. Anderson, H. L. Anderson, J. K. M. Sanders, Acc. Chem. Res. 1993, 26, 469-475; R. Hoss, F. Vögtle, Angew. Chem. 1994, 106, 389-398; Angew. Chem. Int. Ed. Engl. 1994, 33, 375-384; D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725-2828.
15. For recent reviews on unnatural selection in chemical systems and nonenzymatic self-replication see: L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118; E. A. Wintner, M. M. Conn, J. Rebek, Jr., ibid. 1994, 27, 198-203.
16. For recent reviews on unnatural selection in chemical systems and nonenzymatic self-replication see: L. E. Orgel, Acc. Chem. Res. 1995, 28, 109-118; E. A. Wintner, M. M. Conn, J. Rebek, Jr., ibid. 1994, 27, 198-203.
17. All new compounds synthesized were characterized by NMR spectroscopy and high-resolution mass spectrometry.
18. + + Cs] (calcd 749.2064).
19. F. Mohamadi, N. G. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, W. C. Still, J. Comput. Chem. 1990, 11, 440-467.
20. The host-guest chemistry of the dimeric structures 9a,b. and related chiral assemblies will be reported elsewhere.
21. amide-methylated eleven-membered glycolurils.
22. 6]DMSO. The singlets for glycoluril N-H protons and for methyl protons of the aromatic fragments as well as the doublet for the methylene protons of the acetamide group were employed for integration; the estimated error is 10%. The crude mixture was then separated by preparative TLC (silica gel, ethyl acetate as an eluent). The products were analyzed by NMR spectroscopy and FAB-and ESI-MS spectrometry. All the runs were repreated at least twice.
23. -3 M) when the reactants were mixed over 24 h. However, when intramolecular hydrogen bonding was employed, the yields increased up to 88%.
24. -3 M) when the reactants were mixed over 24 h. However, when intramolecular hydrogen bonding was employed, the yields increased up to 88%.
25. -3 M) when the reactants were mixed over 24 h. However, when intramolecular hydrogen bonding was employed, the yields increased up to 88%.
26. -3 M) when the reactants were mixed over 24 h. However, when intramolecular hydrogen bonding was employed, the yields increased up to 88%.
27. C.-W. Su, J. W. Watson, J. Am. Chem. Soc. 1974, 96, 1854-1857; G. D. Titskii, L. M. Litvinenko, J. Gen. Chem. USSR (Russ. Ed.) 1970, 40, 2680-2688.
28. C.-W. Su, J. W. Watson, J. Am. Chem. Soc. 1974, 96, 1854-1857; G. D. Titskii, L. M. Litvinenko, J. Gen. Chem. USSR (Russ. Ed.) 1970, 40, 2680-2688.
29. G. von Kiedrowski, Angew. Chem. 1986, 93, 932-935; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224.
30. G. von Kiedrowski, Angew. Chem. 1986, 93, 932-935; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224.
31. G. von Kiedrowski, Angew. Chem. 1986, 93, 932-935; Angew. Chem. Int. Ed. Engl. 1986, 25, 932-935; D. Sievers, G. von Kiedrowski, Nature 1994, 369, 221-224.
32. D. H. Lee, J. R. Granja, J. A. Martinez, K. Severin, M. R. Ghadiri, Nature, 1996, 382, 525-528.
33. For the kinetic analysis of self-replicating systems that are based on molecular recognition see: J. S. Nowick, Q. Feng, T. Tjivikua, P. Ballester, J. Rebek, Jr., J. Am. Chem. Soc. 1991, 113, 8831-8839; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, ibid. 1996, 118, 6880-6889.
34. For the kinetic analysis of self-replicating systems that are based on molecular recognition see: J. S. Nowick, Q. Feng, T. Tjivikua, P. Ballester, J. Rebek, Jr., J. Am. Chem. Soc. 1991, 113, 8831-8839; D. N. Reinhoudt, D. M. Rudkevich, F. de Jong, ibid. 1996, 118, 6880-6889.