PE(P-16:0e/16:0)
IUPAC 名称
(2-aminoethoxy)[(2R)-3-(hexadec-1-en-1-yloxy)-2-(hexadecanoyloxy)propoxy]phosphinic acid
描述
2-Hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is an intermediate of ether lipid metabolism. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage.
In the ether lipid metabolism pathway, 2-hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine is involved in two enzymatic reactions: 1. It irreversibly produces 1-(1Z-hexadecenyl)-sn-glycero-3-phosphoethanolamine via the enzyme phospholipase A2 (EC:3.1.1.4) and 2. it irreversibly produces 2-hexadecanoyl-1-(1Z-hexadecenyl)-sn-glycero-3-phosphate via the enzyme phospholipase D (EC:3.1.4.4).
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. PEs are neutral zwitterions at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PE synthesis can occur via two pathways. The first requires that ethanolamine be activated by phosphorylation and then coupled to CDP. The ethanolamine is then transferred from CDP-ethanolamine to phosphatidic acid to yield PE. The second involves the decarboxylation of PS.
Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. [HMDB]
异构
[H][C@@](COC=CCCCCCCCCCCCCCC)(COP(O)(=O)OCCN)OC(=O)CCCCCCCCCCCCCCC
InChI标识符
InChI=1S/C37H74NO7P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-32-42-34-36(35-44-46(40,41)43-33-31-38)45-37(39)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h29,32,36H,3-28,30-31,33-35,38H2,1-2H3,(H,40,41)/t36-/m1/s1
键
FDULCEKAOVWBTQ-PSXMRANNSA-N