Reinforcing effect of bi- and tri-cyclopolyprenols on 'primitive' membranes made of polyprenyl phosphates

Tetrahedron

Volumn 63, Issue 16, 2007, Pages 3395-3407

  Ribeiro, Nigel ^a   Streiff, Stéphane ^a   Heissler, Denis ^a   Elhabiri, Mourad ^b   Albrecht Gary, Anne Marie ^b   Atsumi, Michiko ^c   Gotoh, Mari ^a   Désaubry, Laurent ^a   Nakatani, Yoichi ^a   Ourisson, Guy ^a  

^a UNIVERSITÉ LOUIS PASTEUR   (France)

^b Institut de Chimie   (France)

^c OCHANOMIZU UNIVERSITY   (Japan)

Author keywords

Biomimetic synthesis; Lipids; Membranes; Terpenes

Indexed keywords

ALCOHOL DERIVATIVE; BICYCLOPOLYPRENOL; POLYPRENYL PHOSPHATE; TRICYCLOPOLYPRENOL; UNCLASSIFIED DRUG;

ARTICLE; BIOMIMETICS; CELL MEMBRANE; PRIORITY JOURNAL; SYNTHESIS;

EUKARYOTA;

EID: 33947136342     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.01.076     Document Type: Article

References (27)

1. Ourisson G., and Nakatani Y. Chem. Biol. 1 (1994) 11
2. Streiff, S.; Ribeiro, N.; Wu, Z.; Gumienna-Kontecka, E.; Elhabiri, M.; Albrecht-Gary, A. M.; Ourisson, G.; Nakatani, Y. Chem. Biol., in press.
3. Ourisson G., and Albrecht P. Acc. Chem. Res. 25 (1992) 398
4. Krajewski-Bertrand M.A., Hayer M., Wolff G., Milon A., Albrecht A.M., Heissler D., Nakatani Y., and Ourisson G. Tetrahedron 46 (1990) 3143
5. Corey E.J., and Burk R.M. Tetrahedron Lett. 28 (1987) 6413
6. Heissler D., and Ladenburger C. Tetrahedron Lett. 44 (1988) 2513
7. Jenn T., and Heissler D. Tetrahedron 54 (1998) 97
8. Jenn T., and Heissler D. Tetrahedron Lett. 33 (1992) 7227
9. Heissler D., Jenn T., and Nagano H. Tetrahedron Lett. 32 (1991) 7587
10. Raeppel F., and Heissler D. Synlett (2005) 2534
11. For a recent review, see:. Yoder R.A., and Johnston J.N. Chem. Rev. 105 (2005) 4730
12. Streiff S., Ribeiro N., and Désaubry L. J. Org. Chem. 69 (2004) 7592
13. Length of C-Si bond≈1.85 Å, C-C bond≈1.54 Å. Handbook of Chemistry and Physics. 60th ed (1979), CRC, Boca Raton, FL F-216
14. Kodama M., Matsuki Y., and Itoh S. Tetrahedron Lett. 16 (1975) 3065
15. Baldwin J.E., DeBernardis J., and Patrick J.E. Tetrahedron Lett. 5 (1970) 353
16. Edegger K., Mayer S.F., Steinreiber A., and Faber K. Tetrahedron 60 (2004) 583
17. Barton D.H.R., and McCombie S.W. J. Chem. Soc., Perkin Trans. 1 (1975) 1574
18. Altman L.J., Ash L., and Marson S. Synthesis (1974) 129
19. Israelachvili J.N., Mitchell J., and Ninham B.W. Biochim. Biophys. Acta 470 (1977) 185
20. Apel C.L., Deamer D.W., and Mautner M.N. Biochim. Biophys. Acta 1559 (2002) 1
21. Milon A., Lazrak T., Albrecht-Gary A.M., Wolff G., Weill G., Ourisson G., and Nakatani Y. Biochim. Biophys. Acta 859 (1986) 1
22. Slater J.L., and Huang C.H. In: Yeagle P.L. (Ed). Structure of Biological Membranes (2005), CRC, Boca Raton, FL 121-145
23. Demel R.A., and De Kruyff B. Biochim. Biophys. Acta 457 (1976) 109
24. Demel R.A., van Deenen L.L.M., and Pethica B.A. Biochim. Biophys. Acta 135 (1967) 11
25. Demel R.A., Bruckdorfer K.R., and van Deenen L.L.M. Biochim. Biophys. Acta 255 (1972) 321
26. Bisseret P., Wolff G., Albrecht A.M., Tanaka T., Nakatani Y., and Ourisson G. Biochem. Biophys. Res. Commun. 110 (1983) 320
27. Frisch M.J. Gaussian 03, Revision B.03 (2003), Gaussian, Pittsburgh, PA