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J C Ellington

Publications and source records attributed to J C Ellington.

2 recordsLinked to original sources

New structural model for mixed-chain phosphatidylcholine bilayers.

Multilamellar suspensions of a mixed-chain saturated phosphatidylcholine with 18 carbon atoms in the sn-1 chain and 10 carbon atoms in the sn-2 chain have been analyzed by X-ray diffraction techniques. The structural parameters for this lipid in the gel state are quite different than usual phosphatidylcholine bilayer phases. A symmetric and sharp wide-angle reflection at 4.11 A indicates that the hydrocarbon chains in hydrated C(18):C(10)PC bilayers are more tightly packed than in usual gel-state phosphatidylcholine bilayers and that there is no hydrocarbon chain tilt. The lipid thickness is about 12 A smaller than would be expected in a normal bilayer phase, and the area per molecule is 3 times the area per hydrocarbon chain. In addition, the bilayer thickness increases upon melting to the liquid-crystalline state, whereas normal bilayer phases decrease in thickness upon melting. On the basis of these data, we propose a new lipid packing model for gel-state C(18):C(10)PC bilayers in which the long C(18) chain spans the entire width of the hydrocarbon region of the bilayer and the short C(10) chain aligns or abuts with the C(10) chain from the apposing molecule. This model is novel in that there are three hydrocarbon chains per head group at the lipid-water interface. Calculations show that this phase is energetically favorable for mixed-chain lipids provided the long acyl chain is nearly twice the length of the shorter chain. In the liquid-crystalline state C(18):C(10)PC forms a normal fluid bilayer, with two chains per head group.(ABSTRACT TRUNCATED AT 250 WORDS)

Chemical Phenomena↗

Synthesis of mixed-acid phosphatidylcholines and high pressure liquid chromatographic analysis of isomeric lysophosphatidylcholines.

A new method for the synthesis of mixed-chain phosphatidylcholines is reported. Silver ion catalyzed acylation of lysophosphatidylcholines by 2-thiopyridyl esters occurs rapidly (10 min) at room temperature in organic solvents. Yields of isomerically pure mixed-chain phosphatidylcholines (greater than 98% isomeric purity) are generally greater than 80%. The reaction proceeds with only 1.5- to 2-fold excess of thiopyridyl ester, thus offering some advantages over existing procedures when precious acylating agents are used. The major disadvantage of the procedure is its sensitivity to water. Phosphatidylcholines having hydroxy fatty acyl groups are prepared by protection of the hydroxyl as the levulinate ester, conversion to the 2-thiopyridyl ester, acylation, and removal of the levulinate with hydrazine. For purification of lysophosphatidylcholines, a reverse-phase high pressure liquid chromatographic method for separation of 1-acylglycerophosphocholines from 2-acylglycerophosphocholines was developed.

Chromatography, High Pressure Liquid↗