Synthesis and physical properties of phosphatidylcholines containing ω-cyclohexyl fatty acyl chains

✍ Scribed by Tamao Endo; Keizo Inoue; Shoshichi Nojima; Shiro Terashima; Tairo Oshima

• Publisher: Elsevier Science
• Year: 1982
• Tongue: English
• Weight: 683 KB
• Volume: 31
• Category: Article
• ISSN: 0009-3084
• DOI: 10.1016/0009-3084(82)90019-6

✦ Synopsis

Phosphatidylcholines (PCs) with cyclohexyl fatty acids as acyl chains were synthesized from 11-cyclohexyl and 13-cyclohexyl fatty acids and their physical properties were examined. The thermotropic behavior and barrier function of liposomal membranes formed from these PCs were studied. These PCs showed about 10°C lower gel-to-liquid crystalline phase transition temperatures (T c) than the corresponding straight-chain PCs. The properties of mixtures of these cyclohexyl acyl PCs with straight-chain PCs were rather different from those observed with mixtures of straight-chain PCs. Cyclohexyl fatty acyl PCs showed barrier functions even above the T c unlike the corresponding straight-chain PCs. These results indicate significant differences between the overall packing of cyclohexyl fatty acyl PCs and of the corresponding straight-chain PCs both in the gel state and in the liquid crystalline state. The significance of these cyclohexyl acyl chains in polar lipids, which are abundant in the thermophilic acidophilic bacterium, Bacillus acidocaldarius, is discussed.