Influence of cis double bonds in the sn-2 acyl chain of phosphatidylethanolamine on the gel-to-liquid crystalline phase transition

Biophysical Journal

Volumn 73, Issue 1, 1997, Pages 283-292

  Wang, Guoquan ^a   Li, Shusen ^a   Lin, Hai Nan ^a   Huang, C ^a,b  

^a UNIVERSITY OF VIRGINIA HEALTH SYSTEM   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE;

ACYLATION; ANALYTIC METHOD; ARTICLE; CHEMICAL STRUCTURE; DIFFERENTIAL SCANNING CALORIMETRY; FATTY ACID DESATURATION; LIPID BILAYER; MOLECULAR INTERACTION; NONHUMAN; PHASE TRANSITION; PHOSPHOLIPID BILAYER; PHOSPHOLIPID MEMBRANE;

EID: 0031008340     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(97)78069-X     Document Type: Article

References (24)

1. Allinger, N. L., Y. H. Yuh, and J.-H. Lii. 1989. Molecular mechanics. The MM3 force field for hydrocarbons. 1. J. Am. Chem. Soc. 111: 8551-8566.
2. Applegate, K. R., and J. A. Glomset. 1991. Effect of acyl chain unsaturation on the conformation of model diacylglycerols: a computer modeling study. J. Lipid Res. 32:1635-1643.
3. Barton, P. G., and F. D. Gunstone. 1975. Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithin. J. Biol. Chem. 250:4470-4476.
4. Comfurius, P., and R. F. A. Zwall. 1977. The enzymatic synthesis of phosphatidylserine and purification by CM-cellulose column chromatography. Biochim. Biophys. Acta. 488:36-42.
5. Ernst, J., W. S. Sheldrick, and J-H. Fuhrhop. 1979. Die strukturen der essentiellen ungesättigten fettsäuren, kristallstruktur der linolsäure sowie hinweise auf die kristallstrukturen der α-linolensäure und der arachidonsäure. Z. Naturforsch. 34B:706-711.
6. Hernandez-Borrell, J., and K. M. W. Keough. 1993. Heteroacid phosphatidylcholines with different amounts of unsaturation respond differently to cholesterol. Biochim. Biophys. Acta. 1153:277-282.
7. Hitchcock, P. B., R. Mason, K. M. Thomas, and G. G. Shipley. 1974. Structural chemistry of 1,2-dilauroyl-D,L-phosphatidylethanolamine: molecular conformation and intermolecular packing of phospholipids. Proc. Natl. Acad. Sci. USA. 71:3036-3040.
8. Huang, C., S. Li, H-n. Lin, and G. Wang. 1996. On the bilayer phase transition temperatures for monoenoic phosphatidylcholines and phosphatidylethanolamines and the interconversion between them. Arch. Biochem. Biophys. 334:135-142.
9. Huang, C, S. Li, Z-q. Wang, and H-n. Lin. 1993. Dependence of the bilayer phase transition temperature on the structural parameters of phosphatidylcholines. Lipids. 28:365-370.
10. Huang, C., Z-q. Wang, H-n. Lin, E. E. Brumbaugh, and S. Li. 1994. Interconversion of bilayer phase transition temperatures between phosphatidylethanolamines and phosphatidylcholines. Biochem. Biophys. Acta. 1189:7-12.
11. Klein, R. A. 1970. The detection of oxidation in liposomes preparation. Biochim. Biophys. Acta. 210:486-489.
12. Kunau, W-H. 1976. Chemistry and biochemistry of unsaturated fatty acids. Angew. Chem. Int. Ed. Engl. 15:61-74.
13. Li, S., and C. Huang. 1996. Molecular mechanics simulation studies of dienoic hydrocarbons: from alkenes to 1-palmitoyl-2-linoleoyl-phosphatidylcholines. J. Comp. Chem. 17:1013-1024.
14. Li, S., H-n. Lin, G. Wang, and C. Huang. 1996. Effects of alcohols on the phase transition temperatures of mixed-chain phosphatidylcholins. Biophys. J. 70:2784-2794.
15. Lin, H-n., Z-q. Wang, and C. Huang. 1990. Differential scanning calorimetry study of mixed-chain phosphatidylcholines with a common molecular weight identical with diheptadecanoyl phosphatidylcholine. Biochemistry. 29:7063-7072.
16. Litman, B. J., E. N. Lewis, and I. W. Levin. 1991. Packing characteristics of highly unsaturated bilayer lipids: Raman spectroscopic studies of multilamellar phosphatidylcholine dispersions. Biochemistry. 30: 313-319.
17. MacGee, J. 1959. Enzymatic determination of polyunsaturated fatty acids. Anal. Chem. 31:298-302.
18. Mason, J. T., and F. A. Stephenson. 1990. Thermotropic properties of saturated mixed acyl phosphatidylethanolamines. Biochemistry. 29: 590-598.
19. Niebylski, C. D., and N. Salem, Jr. 1994. Calorimetric investigation of a series of mixed-chain polyunsaturated phosphatidylcholines: effects of sn-2 chain length and degree of unsaturation. Biophys. J. 67:2387-2393.
20. Pauling, L. 1960. The Nature of Chemical Bonds, 3rd Ed. Cornell University Press, Ithaca, NY. 138-139.
21. Wang, G., H-n. Lin, S. Li, and C. Huang. 1995. Phosphatidylcholines with sn-1 saturated and sn-2 cis monounsaturated acyl chains: their melting behavior and structures. J. Biol. Chem. 270:22738-22746.
22. Wang, Z-q., H-n. Lin, S. Li, and C. Huang. 1995. Phase transition behavior and molecular structure of monounsaturated phosphatidylcholines: calorimetric studies and molecular mechanics simulations. J. Biol. Chem. 270:2014-2023.
23. Wang, Z-q., H-n. Lin, S. Li, and C. Huang. 1994. Calorimelric studies and molecular mechanics simulations of monounsaturated phosphatidylethanolamine bilayers. J. Biol. Chem. 269:23491-23499.
24. Xu, H., F. A. Stephenson, H. Lin, and C. Huang. 1988. Phase melastability and supercooled metastable state of diundecanoyl phosphatidylethanolamine bilayers. Biochim. Biophys. Acta. 943:63-75.