Chiroptical rhythmicity. Part 1: Description of a novel phenomenon

Enantiomer

Volumn 4, Issue 2, 1999, Pages 121-130

  Ghebremariam, Bereket ^a   Matile, Stefan ^a  

^a GEORGETOWN UNIVERSITY   (United States)

Author keywords

'H' aggregation; Atropisomers; Biphenyl; Circular dichroism; Lipid bilayer; Oligophenylenes; Receptor model

Indexed keywords

LIGAND; PHOSPHATIDYLCHOLINE; RECEPTOR;

ABSORPTION; ARTICLE; CHIROPTICAL RHYTHMICITY; CHROMATOPHORE; CIRCULAR DICHROISM; LIPID BILAYER; PRIORITY JOURNAL; STEREOCHEMISTRY;

CIRCULAR DICHROISM; LIGANDS; LIPID BILAYERS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PHOSPHATIDYLCHOLINES; RECEPTORS, DRUG; STEREOISOMERISM;

GOSSYPIUM HIRSUTUM;

EID: 0032843155     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (46)

1. Some recent examples on chiroptical and other molecular switching devices: (a) E. Yashima, Y. Maeda and Y. Okamoto, J. Am. Chem. Soc. 1998, 120, 8895.
2. (b) D.S. Schlitzer and B.M. Novak, J. Am. Chem. Soc. 1998, 120, 2196.
3. (c) A.E. Rowan and R.J.M. Nolte, Angew. Chem., Int. Ed. Engl. 1998, 37, 63.
4. (d) S.Y. Yang, M.M. Green, G. Schultz, S.K. Jha and A.H.E. Müller, J. Am. Chem. Soc. 1997, 119, 12404.
5. (e) E. Yashima, T. Matsushima and Y. Okamoto, J. Am. Chem. Soc. 1997, 119, 6345.
6. (f) P. Terech and R.G. Weiss, Chem. Rev. 1997, 97, 3133.
7. (g) A.R.A. Palmans, J.A.J.M. Vekemans, E.E. Havinga and E.W. Meijer, Angew. Chem., Int. Ed. Engl. 1997, 36, 2648.
8. (h) B.L. Feringa, N.P.M. Huck and A.M. Schoevaars, Adv. Mater. 1996, 8, 681.
9. (i) N.P.M. Huck, W.F. Jager, B. de Lange and B.L. Feringa, Science 1996, 273, 1686.
10. (j) C.A. Khatri, K. Levon, S.K. Jha and M.M. Green Macromolecules 1995, 28, 4719.
11. (k) M. Fujiki J. Am. Chem. Soc. 1994, 116, 11976.
12. (l) K. Murata, M. Aoki, T. Suzuki, T. Harada, H. Kawabata, T. Komori, F. Ohseto, K. Ueda and S. Shinkai J. Am. Chem. Soc. 1994, 116, 6664.
13. (m) M.M. Green, C. Khatri and N.C. Peterson J. Am. Chem. Soc. 1993, 115, 4941.
14. (n) B.L. Feringa, W.F. Jager and B. de Lange Tetrahedron 1993, 49, 8267.
15. (a) X. Song, J. Perlstein and D.G. Whitten J. Am. Chem. Soc. 1997, 119, 9144.
16. (b) X. Song, C. Geiger, M. Farahat, J. Perlstein and D.G. Whitten J. Am. Chem. Soc. 1997, 119, 12481.
17. (c) H. Chen, M. Farahat, K.Y. Law, J. Perlstein and D.G. Whitten J. Am. Chem. Soc. 1996, 118, 2586.
18. (d) H. Chen, K.Y. Law and D.G. Whitten J. Am. Chem. Soc. 1995, 117, 7257.
19. (e) X. Song, C. Geiger, U. Leinhos, J. Perlstein and D.G. Whitten J. Am. Chem. Soc. 1994, 116, 10340.
20. (f) X. Song, C. Geiger, I. Furman and D.G. Whitten J. Am. Chem. Soc. 1994, 116, 4103.
21. (g) D.G. Whitten Acc. Chem. Res. 1993, 26, 502.
22. (a) M.M. Tedesco, B. Ghebremariam, N. Sakai and S. Matile Angew. Chem., Int. Ed. Engl. 1999, 38, 540;
23. (b) B. Ghebremariam and S. Matile Tetrahedron Lett. 1998, 39, 5335.
24. (a) G.D. Fox, N.K. Dalley and R.G. Harrison J. Am. Chem. Soc. 1998, 120, 7111.
25. (b) N. Bischler, F. Balavoine, H. Tschochner, C. Mioskowski, P. Schultz Biophys. J. 1998, 74, 1522.
26. (c) K.M. Maloney, D.R. Shnek, D.Y. Sasaki and F.H. Arnold Chem. Biol. 1996, 3, 185.
27. (d) K. Ng, D.W. Pack, D.Y. Sasaki and F.H. Arnold Langmuir 1995, 11, 4048.
28. (e) F. Ruan, Y. Chen and P.B. Hopkins J. Am. Chem. Soc. 1990, 112, 9403.
29. (f) P.C. Sinha, V.K. Saxena, N.B. Nigam and M.N. Srivastava Indian J. Chem. 1989, 28, 335.
30. U. De Rossi, S. Dähne, S.C.J. Meskers and H.P.J.M. Dekkers Angew. Chem., Int. Ed. Engl. 1996, 35, 760.
31. B. Boreka, T.S. Cameron, A. Linden, P. Rashidi-Ranjbar and J. Sandström J. Am. Chem. Soc. 1990, 112, 1185, and references therein.
32. J. Sagiv, A. Yogev, Y. Mazur J. Am. Chem. Soc. 1977, 99, 6861.
33. (a) L.A. Weiss, N. Sakai, B. Ghebremariam, C. Ni and S. Matile J. Am. Chem. Soc. 1997, 119, 12142.
34. (b) C. Ni and S. Matile Chem. Commun. 1998, 755.
35. D.K. Struck, D. Hoekstra and R.E. Pagano Biochemistry 1981, 20, 4093.
36. (a) J. Lee and B.R. Lentz Biochemistry 1997, 36, 421.
37. (b) A.-R. Viguera, M. Mencía and F.M. Goña Biochemistry 1993, 32, 3708.
38. (c) L.T. Boni, T.P. Stewart, J.L. Alderler and S.W. Hui J. Membr. Biol. 1981, 62, 65 and 71.
39. T. Pillot, L. Lins, M. Goethals, B. Vanloo, J. Baert, J. Vanderckhove, M. Rosseneu and R. Brasseur J. Mol. Biol. 1997, 274, 381.
40. E.L. Eliel and S.H. Wilen Stereochemistry of Organic Compounds, Wiley: New York, NY, 1993, pp. 1119.
41. K.C. Park, L.R. Dodd, K. Levon and T.K. Kwei Macromolecules 1996, 29, 7149.
42. K.N. Baker, A.V. Fratini, T. Resch, H.C. Knachel, W.W. Adams, E.P. Socci and B.L. Farmer Polymer, 1993, 34, 1571.
43. (a) K. Mislow, M.A.W. Glass, R.E. O'Brien, P. Rutkin, D.H. Steinberg, J. Weiss and C. Djerassi J. Am. Chem. Soc. 1962, 84, 1455.
44. (b) K. Mislow, E. Brunnenberg, R. Records, K. Wellman and C. Djerassi J. Am. Chem. Soc. 1963, 85, 1342.
45. (c) H. Joshua, R. Gans and K. Mislow J. Am. Chem. Soc. 1968, 90, 4884.
46. B. Ghebremariam and S. Matile Enantiomer, following contribution.