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Cell-membrane glycerolipids exhibit a common structural backbone of asymmetric 1,2-diacyl- sn -glycerol bearing polar head groups in the sn -3 position. In this study, the possible effects of sn -3 head groups on the helical conformational property around the 1,2-diacyl moiety in the solution state were examined. 1 H NMR Karplus relation studies were carried out using a series of 1,2-dipalmitoyl- sn -glycerols bearing different sn -3 substituents (namely palmitoyl, benzyl, hydrogen, and phosphates). The 1 H NMR analysis indicated that the helical property around the 1,2-diacyl moiety is considerably affected by these sn -3 substituents. The sn -3 hydroxy group induced a unique helical property, which was considerably dependent on the solvents used. In CDCl 3 solution, three staggered conformers, namely gt(+), gg(-) and tg, were randomized, while in more polar solvents, the gt(+) conformer with (+)-helicity was amplified at the expense of gg(-) and tg conformers. The sn -3 phosphocholine in phosphatidylcholine exhibited a greater effect on the gt(+) conformer, which was independent of the solvents used. From the 1 H NMR analysis, the helical conformational properties around the 1,2-diacyl moiety conformed to a simple empirical rule, which permitted the proposal of a conformational diagram for 1,2-dipalmitoyl- sn -glycerols in the solution states.

beilstein journal of organic chemistry

Remarkable functions of sn-3 hydroxy and phosphocholine groups in 1,2-diacyl-sn-glycerolipids to induce clockwise (+)-helicity around the 1,2-diacyl moiety: Evidence from conformation analysis by 1H NMR spectroscopy