A synthetic transmembrane polyether model active in lipid bilayers

Organic Letters

Volumn 2, Issue 20, 2000, Pages 3161-3164

  Espínola, Carmen G ^a   Pérez, Ricardo ^a   Martín, Julio D ^a  

^a INSTITUTO DE INVESTIGACIONES QUÍMICAS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ETHER DERIVATIVE; POLYMER; POTASSIUM CHANNEL; SODIUM;

ARTICLE; ARTIFICIAL MEMBRANE; CHEMICAL STRUCTURE; CHEMISTRY; LIPID BILAYER; PROTEIN CONFORMATION; SYNTHESIS;

ALKENES; ETHERS; LIPID BILAYERS; MEMBRANES, ARTIFICIAL; MODELS, MOLECULAR; POLYMERS; POTASSIUM CHANNELS; PROTEIN CONFORMATION; SODIUM RADIOISOTOPES;

EID: 0034609679     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0063555     Document Type: Article

References (47)

1. (a) Doyle, D. A.; Morais-Cabral, J.; Pfuetzner, R. A.; Kuo, A.; Gulbis, J. M.; Cohen, S. L.; Chait, B. T.; Mackinnon, R. Science 1998, 280, 69-77.
2. (b) Mackinnon, R.; Cohen, S. L.; Kuo, A.; Lee, A.; Chait, B. T. Science 1998, 280, 106-109.
3. (c) Kreusch, A.; Pfaffinger, P. J.; Stevens, C. F.; Choe, S. Nature 1998, 392, 945-948.
4. Reviews related with synthetic models for transmembrane channels: (a) Gokel, G. W.; Murillo, O. Acc. Chem. Res. 1996, 29, 425-432.
5. (b) Fyles, T. M.; Straaten-Nijenhuis, W. F. In Comprehensive Supramolecular Chemistry; Reinhoudt, D. N., Ed.; Elsevier Science Ltd.: Oxford, 1996; Vol. 10, pp 53-77.
6. (c) Voyer, N. Top. Curr. Chem. 1996, 184, 1-37.
7. (d) Akerfeldt, K. S.; Lear, J. D.; Wasserman, Z. R.; Chung, L. A.; DeGrado, W. F. Acc. Chem. Res. 1993, 26, 191-197.
8. Incorporation of macromolecular polyether derivatives into lipids has been shown to result in cation transport rates comparable to those ion channels formed by natural and synthetic oligopeptides or antifungal macrolides: (a) Fyles, T. M.; Loock, D.; Zhou, X. J. Am. Chem. Soc. 1998, 120, 2997-3003.
9. (b) Meillon, J.-C.; Voyer, N. Angew. Chem. 1997, 109, 1004-1006; Angew. Chem., Int. Ed. Engl. 1997, 36, 967-968.
10. (b) Meillon, J.-C.; Voyer, N. Angew. Chem. 1997, 109, 1004-1006; Angew. Chem., Int. Ed. Engl. 1997, 36, 967-968.
11. (c) Pechulis, A. D.; Thompson, R. J.; Fojtik, J. P.; Schwartz, H. M.; Lisek, C. A.; Frye, L. L. Bioorg. Med. Chem. 1997, 38, 6339-6342.
12. (d) Abel, E.; Meadows, E. S.; Suzuki, I.; Jin, T.; Gokel, G. W. J. Chem. Soc., Chem. Commun. 1997, 1145-1146.
13. (e) Murray, C. L.; Meadows, E. S.; Murillo, O.; Gokel, G. W. J. Am. Chem. Soc. 1997, 119, 7887-7888.
14. (f) Murillo, O.; Suzuki, I.; Abel, E.; Murray, C. L.; Meadows, E. S.; Jin, T.; Gokel, G. W. J. Am. Chem. Soc. 1997, 119, 5540-5549.
15. (g) Matile, S.; Nakanishi, K. Angew. Chem. 1996, 108, 812-814; Angew. Chem., Int. Ed. Engl. 1996, 35, 757-759.
16. (g) Matile, S.; Nakanishi, K. Angew. Chem. 1996, 108, 812-814; Angew. Chem., Int. Ed. Engl. 1996, 35, 757-759.
17. (h) Stadler, E.; Dedek, P.; Yamashita, K.; Regen, S. L. J. Am. Chem. Soc. 1994, 116, 6677-6682 and references therein.
18. Length refers to distance among pyran oxygens in fully extended polyoxyethylene chains and was calculated by molecular mechanics routine.
19. For general reviews on olefm metathesis in organic synthesis, see: (a) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: New York, 1997.
20. (b) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2145; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
21. (b) Schuster, M.; Blechert, S. Angew. Chem. 1997, 109, 2124-2145; Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
22. (c) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
23. For preparation of Ru-catalyst, see: (a) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
24. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179-2181; Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
25. (b) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. Angew. Chem. 1995, 107, 2179-2181; Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
26. (d) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Shem. Soc. 1996, 118, 100-110.
27. 2.
28. n OTs (n = 4) (1.5 equiv), 1 h.
29. + requires 733.86).
30. (a) Arakawa, K.; Eguchi, T.; Kakinuma, K. J. Org. Chem. 1998, 63, 4741-4745.
31. (b) Pitarch, M.; Mckee, V.; Nieuwenhuyzen, M.; Mckervey, M. A. J. Org. Chem. 1998, 63, 946-951.
32. (c) Zuercher, W. J.; Hashimoo, M.; Grubbs, R. J. J. Am. Chem. Soc. 1996, 118, 6634-6640.
33. + requires 1400.67).
34. 2, 20 mol % cat.
35. Heginbotham, L.; Lu, Z.; Abramson, T.; MacKinnon, R. Biophys. J. 1994, 66, 1061-1064.
36. (a) Petti, M. A.; Shepodd, T. J.; Barrans, R. E., Jr.; Dougherty, D. A. J. Am. Chem. Soc. 1988, 110, 6825-6840.
37. (b) Kearney, P. C.; Mizoue, L. S.; Kumpf, R. A.; Forman, J. E.; McCurdy, A.; Dougherty, D. A. J. Am. Chem. Soc. 1993, 115, 9907-9919.
38. (c) Maguire, G. E. M.; Meadows, E. S.; Murray, C. L.; Gokel, G. W. Tetrahedron Lett. 1997, 38, 6339-6342.
39. Ovchinnikov, Yu.; Abdulaev, N.; Feizina, M.; Kiselev, A.; Lobanov, N. FEBS Lett. 1979, 100, 219-224.
40. Abel, E.; Feeders, M. F.; Gokel, G. W. J. Am. Chem. Soc. 1995, 117, 1265-1270.
41. + requires 2157.70).
42. Riddell, F. G.; Hayer, M. K. Biochim. Biophys. Acta 1985, 817, 313-317.
43. Buster, D. C.; Hinton, J. F.; Millett, F. S.; Shungu, D. C. Biophys. J. 1988, 53, 145-152.
44. Mimms, L. T.; Zanpighi, G.; Nozaki, Y.; Tanford, C.; Reynolds, J. A. Biochemistry 1981, 20, 833-840.
45. For an excellent conformational study of polyethylene/polyoxyethylene oligomers in solid state, see: Chem, Y.; Baker, G. L.; Ding, Y.; Rabolt, J. F. J. Am. Chem. Soc. 1999, 121, 6962-6963.
46. For a previous study of cell-surface receptors based on rigid-rod molecules, see: Ghebremariam, B.; Matile, S. Tetrahedron Lett. 1998, 39, 5335-5338.
47. A further account of work in this area will appear in an issue of the Israel Journal of Chemistry honoring the Canadian chemist Professor Raymond U. Lemieux.