PG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z))
IUPAC 名称
[(2S)-2,3-dihydroxypropoxy][(2R)-2-(docosa-4,7,10,13,16-pentaenoyloxy)-3-(octadec-9-enoyloxy)propoxy]phosphinic acid
描述
PG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PG(18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of docosapentaenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the docosapentaenoic acid moiety is derived from animal fats and brain. Phosphatidylglycerol is present at a level of 1-2% in most animal tissues, but it can be the second most abundant phospholipid in lung surfactant at up to 11% of the total. It is well established that the concentration of phosphatidylglycerol increases during fetal development. Phosphatidylglycerol may be present in animal tissues merely as a precursor for diphosphatidylglycerol (cardiolipin). Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases.
While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PGs have a net charge of -1 at physiological pH and are found in high concentration in mitochondrial membranes and as components of pulmonary surfactant. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate. [HMDB]
异构
[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCC=CCCCCCCCC)OC(=O)CCC=CCC=CCC=CCC=CCC=CCCCCC
InChI标识符
InChI=1S/C46H79O10P/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-46(50)56-44(42-55-57(51,52)54-40-43(48)39-47)41-53-45(49)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h11,13,17-19,21-23,26,28,32,34,43-44,47-48H,3-10,12,14-16,20,24-25,27,29-31,33,35-42H2,1-2H3,(H,51,52)/t43-,44+/m0/s1
键
JKAAWGKTGRIKRC-JCGOJSMZSA-N