Resolution and chromatographic configuration analysis of 2-hydroxy fatty acids.
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Biomedical subjects
Publications and source records attributed to I Pascher.
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Ceramides with mono-, di-, and trihydroxy long-chain bases, and normal (saturated and unsaturated), branched-chain, and 2-hydroxy fatty acids have been analyzed by thin-layer chromatography. In most cases the compounds were also run as acetates. Borate, arsenite, and silver ions were used as complexing agents, and the effects of number, position, and stereochemistry of hydroxy groups, and of unsaturation, were studied. The results are discussed in view of analysis of natural ceramide species.
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The packing arrangement and molecular conformation of lysophosphatidate (disodium 3-lauroyl-DL-glycero-1-phosphate dihydrate (LPA] was determined by single crystal analysis. The lipid crystallizes in the triclinic space group P1 with unit cell dimensions of a = 7.74, b = 5.54, c = 32.87 A and alpha = 92.6, beta = 99.2, gamma = 128.3 degrees. The molecules are arranged tail to tail in a bilayer structure. Thereby the D- and L-enantiomers pack separately in the opposite halves of the bilayer and are conformationally related by mirror symmetry. The hydrocarbon chains adopt the triclinic (T parallel) chain packing mode and are tilted by 55 degrees with respect to the layer normal. The phosphate groups are linked by one of the sodium ions to tightly packed rows. Between these rows the second sodium ion and the two water molecules of hydration are accommodated forming an extensive network of hydrogen, ionic and coordination bonds. The two sodium ions are positioned 1 A below and above the plane defined by the centres of gravity of the phosphate charges. The phosphate group and its 4 ligands thus pack effectively with a small cross-sectional area in the layer plane of 33.6 A2.