STRUCTURE AND POLYMORPHISM OF SATURATED MONOACID 1,2-DIACYL-SN-GLYCEROLS

被引:38
作者
KODALI, DR [1 ]
FAHEY, DA [1 ]
SMALL, DM [1 ]
机构
[1] BOSTON UNIV,SCH MED,HOUSMAN MED RES CTR,DEPT BIOPHYS,80 E CONCORD ST,BOSTON,MA 02118
关键词
D O I
10.1021/bi00500a008
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The 1,2-diacyl-sn-glycerols (1,2-DGs) are the predominant naturally occurring isomer found in cell membranes, lipid droplets, and lipoproteins. They are involved in the metabolism of monoacylglycerols, triacylglycerols, and phospholipids. The 1,2-DGs participate in the activation of protein kinase C, in phosphorylation of target proteins, and in transduction of extracellular signals into the cell. We have undertaken a study of the physical properties of a homologous series of synthetic optically active diacyl-glycerols. Stereospecific 1,2-diacyl-sn-glycerols were synthesized with saturated fatty acyl chains of 12, 16, 18, 22, and 24 carbons in length. Their polymorphic behavior was examined by differential scanning calorimetry and X-ray powder diffraction. The solvent-crystallized form for all the 1,2-DGs packs in the orthorhombic perpendicular subcell (β′) and melts with a single sharp endotherm to an isotropic liquid. On quenching, the C12, C16 and C18 compounds pack in a hexagonal subcell (α), whereas the C22 and C24 pack in a pseudohexagonal subcell (sub-α). The sub-α phase reversibly converts to the α phase. The long spacings of these compounds in both the α and β′ phases increase with chain length. In the α and β′ phases, the acyl chain tilts were found to be 90° and 62° from the basal methyl plane. The polymorphic behavior of 1,2-diacyl-sn-glycerol is quite different from that of the corresponding monoacid saturated 1,3-diacylglycerols which form two β phases with triclinic parallel subcells. © 1990, American Chemical Society. All rights reserved.
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页码:10771 / 10779
页数:9
相关论文
共 34 条
[1]  
[Anonymous], 1977, EUR J BIOCHEM, V79, P11
[2]   THE POLYMORPHISM OF SATURATED 1,3-DIGLYCERIDES [J].
BAUR, FJ ;
JACKSON, FL ;
KOLP, DG ;
LUTTON, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (10) :3363-3366
[3]   EFFICIENT SYNTHESIS OF SYMMETRICAL 1,3-DIGLYCERIDES [J].
BENTLEY, PH ;
MCCRAE, W .
JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (06) :2082-&
[4]   AN X-RAY AND THERMAL EXAMINATION OF THE GLYCERIDES .8. GLYCERIDES OF ERUCIC, BRASSIDIC, OLEIC, AND ELAIDIC ACIDS [J].
CARTER, MGR ;
MALKIN, T .
JOURNAL OF THE CHEMICAL SOCIETY, 1947, (APR) :554-&
[5]   POLYMORPHISM OF GLYCERIDES [J].
CHAPMAN, D .
CHEMICAL REVIEWS, 1962, 62 (05) :433-&
[6]   POLYMORPHISM OF 1,2 DIPALMITOYLGLYCERIDE [J].
CRAIEVICH, AF ;
LEVELUT, AM ;
LAMBERT, M ;
ALBON, N .
JOURNAL DE PHYSIQUE, 1978, 39 (04) :377-388
[7]   X-RAY INVESTIGATION OF GLYCERIDES .7. DIFFRACTION ANALYSES OF SYNTHETIC 1,3-DIELAIDIN [J].
DAUBERT, BF ;
SIDHU, SS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1948, 70 (05) :1848-1849
[8]   X-RAY DIFFRACTION ANALYSES OF SYNTHETIC UNSATURATED MONACID DIGLYCERIDES [J].
DAUBERT, BF ;
LUTTON, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1947, 69 (06) :1449-1451
[9]   ELECTRON-DIFFRACTION STUDY OF ALPHA-POLYMORPHIC FORM OF A DIGLYCERIDE [J].
DORSET, DL .
CHEMISTRY AND PHYSICS OF LIPIDS, 1974, 13 (02) :133-140
[10]   POLYMORPHIC FORMS OF 1,2-DIPALMITOYL-SN-GLYCEROL - A COMBINED X-RAY AND ELECTRON-DIFFRACTION STUDY [J].
DORSET, DL ;
PANGBORN, WA .
CHEMISTRY AND PHYSICS OF LIPIDS, 1988, 48 (1-2) :19-28