Controlling the secondary structure of nonbiological oligomers with solvophobic and coordination interactions

Angewandte Chemie - International Edition

Volumn 38, Issue 1-2, 1999, Pages 233-236

  Prince, Ryan B ^a   Okada, Takashi ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Conformation analysis; Coordination chemistry; Helical structures; Oligomers; Supramolecular chemistry

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; STRUCTURE ANALYSIS;

EID: 0033555217     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990115)38:1/2<233::AID-ANIE233>3.0.CO;2-Y     Document Type: Article

References (27)

1. S. H. Gellman, Acc. Chem. Res. 1998, 31, 173-180.
2. J. L. Matthews, D. Seebach, Chem. Commun. 1997, 2015-2022.
3. Y. Hamuro, S. J. Geib, A. D. Hamilton, J. Am. Chem. Soc. 1997, 119, 10587-10593.
4. R. S. Lokey, B. L. Iverson, Nature 1995, 375, 303-305.
5. D. Bassani, J.-M. Lehn, G. Baum, D. Fenske, Angew. Chem. 1997, 109, 1931-1933; Angew. Chem. Int. Ed. Engl. 1997, 36, 1845-1847.
6. D. Bassani, J.-M. Lehn, G. Baum, D. Fenske, Angew. Chem. 1997, 109, 1931-1933; Angew. Chem. Int. Ed. Engl. 1997, 36, 1845-1847.
7. A. Rigault, J. Siegel, J. Harrowfield, B. Chevrier, D. Moras, J.-M. Lehn, Proc. Natl. Acad. Sci. USA 1987, 84, 2566-2569.
8. T. M. Garrett, U. Koert, J.-M. Lehn, A. Rigault, D. Meyer, J. Fischer, J. Chem. Soc. Chem. Commun. 1990, 557-558.
9. A. Williams, Chem. Eur. J. 1997, 3, 15-19.
10. C. Piquet, G. Bernardinelli, G. Hopfgartnet, Chem. Rev. 1997, 97, 2005-2062.
11. J. C. Nelson, J. G. Saven, J. S. Moore, P. G. Wolynes, Science 1997, 277, 1793-1796.
12. A. Ben-Naim, J. Phys. Chem. 1971, 54, 1387-1404.
13. 1H NMR and UV/Vis spectroscopy. Thus, the secondary structure of 3 can be controlled using a solvophobic driving force, and the cyano groups on the interior of the tubular cavity do not appear to inhibit the formation of helical structures.
14. 1H NMR spectroscopy, size-exclusion chromatography, high-performance liquid chromatography, and matrix-assisted laser desorption ionization mass spectrometry (MALDI-MS). Compounds 2 and 3 gave acceptable elemental analyses. Further details of the preparation and characterization of all compounds will be reported elsewhere.
15. For examples of preorganized, ion-binding systems substituted with cyano groups, see a) K. Paek, C. B. Knobler, E. F. Maverick, D. J. Cram, J. Am. Chem. Soc. 1989, 74, 8662-8671:
16. b) Y. Tobe, N. Utsumi, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. 1998, 37, 1285-1287.
17. b) Y. Tobe, N. Utsumi, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349; Angew. Chem. Int. Ed. 1998, 37, 1285-1287.
18. R. H. P. Francisco, Y. P. Mascarehnas, J. R. Lechat, Acta Crystallogr. Sect. B 1979, 35, 177-178.
19. L. Carlucci, G. Ciani, D. Prosperpio, A. Sironi, J. Am. Chem. Soc. 1995, 117, 4562-4569.
20. D. Venkataraman, Y. Du, S. Wilson, K. Hirsch, P. Zhang, J. Moore, J. Chem. Ed. 1997, 74, 915.
21. 2+ ions prefer a square-planar or octahedral bonding geometry.
22. 2+.
23. The NMR spectra of 3 are similiar to those of 5, but there are twice as many resonances.
24. K. Wuthrich, NMR of Proteins and Nucleic Acids, Wiley, New York, 1986.
25. 3 to a solution in THF results in broad, undefined signals in the aromatic region, characteristic of a system that is fluctional on the NMR time scale.
26. K. A. Connors, Binding Constants: The Measurement of Molecular Complex Stability. Wiley, New York, 1987.
27. The UV/Vis spectra showed a clear isobestic point at 375 nm. indicative of only one species being formed upon complexation.