Effect of acyl chain unsaturation on the conformation of model diacylglycerols: a computer modeling study.
In a previous modeling study we identified an angle iron-shaped conformation of docosahexaenoic acid and showed that an sn-1-stearoyl diacylglycerol (DG) that contained an sn-2-docosahexaenoyl group in this conformation could adopt a highly regular shape. In the present study we compared the properties of this DG with those of sn-1-stearoyl DGs that contained other unsaturated fatty acyl groups in the sn-2 position. The major findings were that: 1) sn-1-stearoyl DGs that contain polyenoic fatty acids in the sn-2 position can assume regular shapes, and 2) these shapes differ depending on the location of the double bonds. sn-2-Polyenoic fatty acyl groups with a double bond sequence that begins close to the carboxyl ester bond are associated with one type of regular shape, while sn-2-polyenoic fatty acyl groups with a double bond sequence that begins toward the middle of the chain are associated with another. Such shapes would not have been predicted by current ideas relating membrane fluidity to unsaturation. In contrast, another finding of the present study, that sn-1-stearoyl-2-oleoyl DG can adopt, at best, only a highly irregular shape is in good agreement with the results of previous investigators.
Applegate
K R
KR
Department of Biochemistry, University of Washington, Seattle 98195.
Glomset
J A
JA
D000215:Acylation; D003198:Computer Simulation; D004075:Diglycerides / Q000737:chemistry*; D005224:Fats, Unsaturated / Q000737:chemistry; D008968:Molecular Conformation; D013229:Stearic Acids / Q000737:chemistry
D004075:Diglycerides; D005224:Fats, Unsaturated; D013229:Stearic Acids; C031183:stearic acid