Design and synthesis of asymmetric acyclic phospholipid bolaamphiphiles

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2606-2615

  Kai, Toshitsugu ^a   Sun, Xue Long ^a   Faucher, Keith M ^a   Apkarian, Robert P ^b   Chaikof, Elliot L ^a,c  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b EMORY UNIVERSITY   (United States)

^c Georgia Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MEMBRANES; NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; SELF ASSEMBLY; SYNTHESIS (CHEMICAL);

ALKYLDIOIC ACID; LIPID BOLAAMPHIPHILES; MEMBRANE-MIMETIC STRUCTURE;

PHOSPHOLIPIDS;

ACID; AMINE; AMPHOPHILE; PHOSPHATIDYLCHOLINE; SOLVENT; WATER;

ARTICLE; ENGINEERING; ESTERIFICATION; INFRARED SPECTROSCOPY; MEMBRANE STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SCANNING ELECTRON MICROSCOPY; SYNTHESIS;

MAGNETIC RESONANCE SPECTROSCOPY; MICROSCOPY, ELECTRON, SCANNING; MOLECULAR STRUCTURE; PHOSPHOLIPIDS; SOLVENTS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 17044371960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048167o     Document Type: Article

References (36)

1. Fuhrhop, J.-H.; Koning, J. Membranes and Molecular Assemblies: The Synkinetic Approach; The Royal Society of Chemistry: London, 1994.
2. Sackmann, E.; Tanaka, M. Trans Biotechnol. 2000, 18, 58-64.
3. Lamparski, H.; Liman, U.; Frankel, D. A.; Ramaswami, V.; Brown, M. F.; O'Brien, D. F. Biochemistry 1992, 31, 685-694.
4. Plant, A. L. Langmuir 1993, 9, 2764-2767.
5. Plant, A. L.; Brigham-Burke, M.; Petrella, E. C.; O'Shannessy, D. J. Anal. Biochem. 1995, 226, 342-348.
6. O'Brien, D. F.; Armitage, A. B.; Bennett, D. E.; Lamparski, H. G.; Lee Y.-S.; Srisiri, W.; Sisson, T. M. Acc. Chem. Res. 1998, 31, 861-868.
7. Kusumi, A.; Singh, M.; Tirrell, D. A.; Oehme, G.; Singh, A.; Samuel, N. K. P.; Hyde, J. S.; Regen, S. L. J. Am. Chem. Soc. 1983, 105, 2975-2980.
8. Ohkatsu, Y. M.; Yokatsu, M.; Kusano, T. Makromol. Chem. 1988, 189, 775-760.
9. O'Brien, D. F.; Klingbiel, R. T.; Whitesides, T. H. J. Polym. Sci. Polym. Lett. Ed. 1981, 19, 95-101.
10. Lamparski, H.; Lee, Y. S.; Sells, T. D.; O'Brien, D. F. J. Am. Chem. Soc. 193, 115, 8096-102.
11. Sells, T. D.; O'Brien, D. F. Macromolecules 1994, 27, 226-33.
12. Sisson, T. M.; Lamparski, H. G.; Koelchens, S.; Elayadi, A.; O'Brien, D. F. Macromolecules 1996, 29, 8321-8329.
13. Lamparski, H. G.; Oblinger, E.; O'Brien, D. F. Macromolecules 1999, 32, 5450-5452.
14. Marra, K. G.; Winger, T. M.; Hanson, S. R.; Chaikof, E. L. Macromolecules 1997, 30, 6483-6488.
15. Orban, J. M.; Faucher, K. M.; Dluhy, R. A.; Chaikof, E. L. Macromolecules 2000, 33, 4205-4212.
16. Sun, X.-L.; Liu, H.; Orban, J. M.; Sun. L.; Chaikof, E. L. Bioconjugate Chem. 2001, 12, 673-677.
17. Liu, H.; Faucher, K. M.; Sun, X.-L.; Feng, J.; Johnson, T. L.; Orban, J. M.; Apkarian, R. D.; Dluhy, R. A.; Chaikof, E. L. Langmuir 2002, 18, 1332-1339.
18. De Rosa, M.; Gambacorta, A.; Gliozzi, A. Microbiol. Rev. 1986, 50, 70-80.
19. Setter, K. O. FEMS Microbiol. Rev. 1996, 18, 149-158.
20. Cornell, B. A.; Braach-Maksvytis, V. L. B.; King, L. G.; Osman, P. D. J.; Ragase, B.; Wieczoreck, L.; Pace, R. J. Nature 1997, 387, 580-583.
21. Wang, G.; Hollingsworth, R. I. J. Org. Chem. 1999, 64, 4140-4147.
22. Moss, R. A.; Fujita, T.; Okumura, Y. Langmuir 1991, 7, 2415-2418.
23. Kim, J.-M.; Thompson, D. H. Langmuir 1992, 8, 637-644.
24. Menger, F. M.; Chen, X. Y.; Brocchini, S.; Hopkins, H. P.; Hamilton, D. J. Am. Chem. Soc. 1993, 115, 6600-6608.
25. Menger, F. M.; Littau, C. A. J. Am. Chem. Soc. 1993, 115, 10083-10090.
26. Heiser, U. F.; Dobner, B. J. Chem. Soc., Perkin Trans. 1 1997, 809-815.
27. Eguchi, T.; Arakawa, K.; Terachi, T.; Kakinuma, K. J. Org. Chem. 1997, 62, 1924-1933.
28. Svenson, S.; Thompson, D. H. J. Org. Chem. 1998, 63, 7180-7182.
29. Lecollinet, G.; Auzély-Velty, R.; Daniel, M.; Benvegnu, T.; Mackenzie, G.; Goodby, J. W.; Plusquellec, D. J. Org. Chem. 1999, 64, 3139-3150.
30. Miyawaki, K.; Takagi, T.; Shibakami, M. Synlett 2002, 1326-1328.
31. Collier, J. H.; Messersmith, P. B. Annu. Rev. Mater. Res. 2001, 31, 237-263.
32. Paulain, S.; Noiret, N.; Fauconnot, L.; Nugier-Chauvin, C.; Patin, H. Tetrahedron 1999, 55, 3595-3604.
33. Hebert, N.; Beck. A.; Lennox, R. B.; Just, Q. J. Org. Chem. 1992, 57, 1777-1783.
34. Winnik, F. M.; Miyazawa, K. Macromolecules 2002, 35, 2440-2444.
35. Blume, A.; Hübner, W.; Messner, G. Biochemistry 1988, 27, 8239-8249.
36. Domingo, J. C.; Madariaga, M. A. D. Collo. Surf. A: Physichem. Eng. Aspects 1996, 115, 97-105.