Glycerophospholipid Metabolism

Glycerol is the backbone of the fundamental phospholipids used as the self-assembling units of lipid membranes. It is interesting that both enantiomeric glycerol configurations appear in nature. In eukaryotes and eubacteria, glycerophospholipids are based on the sn -3 configuration of the glycerol backbone, while archaebacteria lipids are based on the sn -1-configuration. The metabolic intermediate for all glycerophospholipids is phosphatidic acid (1,2-diacylglycerol-3-phosphate). Lysophosphatidic acid, which lacks the acyl chain in the 2-position, is an important cellular messenger.

Phosphatidylcholine (lecithin) is the most abundant phospholipid in animal and plant tissues. Phosphatidylethanolamine (cephalin) is an abundant phospholipid in microbial, plant, and animal cells. The corresponding lysophosphatidic acid derivatives, lysophosphatidylcholine and lysophosphatidylethanolamine, are more soluble in water and have surfactant properties, and these are not standard components of cell membranes. Phosphatidylglycerol has important functions in lung surfactants, chloroplasts, and bacterial membranes and is a metabolic intermediate in the biosynthesis of cardiolipin. Phosphatidylserine is involved in biological processes including apoptosis, blood coagulation, and activation of protein kinase C. It can be found in plasma membranes and other membranes of animals, plants, and microorganisms.

A class of phospholipids with a high rate of metabolism is the phosphatidylinositols which have varying degrees of phosphorylation in the polar head group myo-inositol. The metabolic conversion of phosphatidylinositols to diacylglycerols and inositol phosphates is important in the regulation of vital cellular functions such as differentiation, proliferation, and apoptosis, and in anchoring proteins via a glycosyl-bridge to the plasma membrane.

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D2907 1,2-Didodecanoyl-3-tetradecanoyl-rac-glycerol ≥99%  
77017 1,2-Dierucoyl-sn-glycero-3-phosphocholine ≥98.0% (TLC)  
74576 1,2-Dierucoyl-sn-glycero-3-phosphoethanolamine ≥98% (TLC)  
80114 1,2-Dimyristoyl-sn-glycero-3-phospho-L-serine sodium salt ≥70% (TLC)  
D9925 1,2-Dioleoyl-3-linoleoyl-rac-glycerol liquid, 97% (TLC)  
D1782 1,2-Dioleoyl-3-palmitoyl-rac-glycerol ≥99% (TLC)  
D2032 1,2-Dioleoyl-3-stearoyl-rac-glycerol ~99%  
D3532 1,2-Dipalmitoyl-3-myristoyl-rac-glycerol ~99%  
P4240 1,2-Dipalmitoylphosphatidylinositol 3,4,5-trisphosphate tetrasodium salt ≥98% Proposed as signal transduction modulator.
P7115 1,2-Dipalmitoylphosphatidylinositol 4,5-diphosphate triammonium salt ≥98%, solid Diphosphorylated phosphatidylinositol that may be hydrolyzed by PI-specific phospholipase C to generate IP3 and DAG.
43307 1,2-Distearoyl-sn-glycero-3-phospho-L-serine sodium salt ≥75% (TLC)  
P1527 1,2-Di-O-hexadecyl-sn-glycero-3-phosphocholine ≥99% (TLC)  
P9898 1,2-Diarachidoyl-sn-glycero-3-phosphocholine ≥99% (TLC)  
P3142 1,2-Dibutyryl-sn-glycero-3-phosphocholine 20 mg/mL in chloroform: methanol (3:1), solution, ≥99%  
P7081 1,2-Didecanoyl-sn-glycero-3-phosphocholine ≥99% (TLC)  
P2342 1,2-Didocosanoyl-sn-glycero-3-phosphocholine ≥99% (TLC)  
P1534 1,2-Didodecanoyl-rac-glycero-3-phosphocholine ≥99%  
P1263 1,2-Didodecanoyl-sn-glycero-3-phosphocholine ≥99%, synthetic  
P9202 1,2-Dielaidoyl-sn-glycero-3-phosphocholine ≥98% (GLC, TLC)  
00259 1,2-Dierucoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥98.0% (TLC)  
P8664 1,2-Diheptadecanoyl-sn-glycero-3-phosphoethanolamine ≥99% (GC)  
P5650 1,2-Dihexadecanoyl-rac-glycero-3-phospho-rac-(1-glycerol) ammonium salt ≥99% (GC)  
P3777 1,2-Dihexadecyl-rac-glycero-3-phosphocholine ≥99% (TLC)  
37161 1,2-Dihexadecyl-sn-glycero-3-phosphoethanolamine ≥99.0% (TLC)  
P0537 1,2-Dilinoleoyl-sn-glycero-3-phosphocholine ≥99% (TLC), lyophilized powder  
P7930 1,2-Dimyristoyl-rac-glycero-3-phosphocholine ≥99%  
P2663 1,2-Dimyristoyl-sn-glycero-3-phosphocholine ≥99%  
P7331 1,2-Dimyristoyl-sn-glycero-3-phosphocholine synthetic, ~99%  
P5693 1,2-Dimyristoyl-sn-glycero-3-phosphoethanolamine synthetic, ≥99%  
P3650 1,2-Dimyristoyl-sn-glycero-3-phosphate monosodium salt ≥99%  
43096 1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt ≥97.0% (TLC)  
90998 1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥98.0% (TLC)  
P6412 1,2-Dimyristoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥99%  
C5430 1,2-Dimyristoyl-sn-glycerol-3-(5′-diphosphocytidine) potassium salt ~90%  
P8648 1,2-Dinonanoyl-sn-glycero-3-phosphocholine 20 mg/mL in chloroform, ~99% (TLC)  
05717 1,2-Dioctadecanoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt ≥98.0% (TLC) DSPG is the most efficient phosphatidylglycerol in enhancing respiratory mucus clearance in cystic fibrosis.
P6354 1,2-Dioleoyl-sn-glycero-3-phosphocholine lyophilized powder  
76548 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine ≥97.0% (TLC) DOPE in mixed membranes have been found to decrease fluorescence lifetime and increase acyl-chain order. DOPE is an essential component of cationic liposomes designed to deliver DNA into gliosarcoma and kidney cell lines (gene therapy).
42490 1,2-Dioleoyl-sn-glycero-3-phosphoethanolamine ≥99.0% (10 mg phospholipid per ml CHCl3, TLC)  
P1060 1,2-Dioleoyl-sn-glycero-3-phospho-L-serine sodium salt ~95%  
74384 1,2-Dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥98.0% (TLC) Remodeling of diacylphosphatidylglycerols by transesterification was studied in a phosphatidylglycerol-deficient microbe grown with exogenous DOPG.
P9664 1,2-Dioleoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt solution, 10 mg/mL in chloroform, ≥99%  
42491   1,2-Dioleoyl-sn-glycero-3-phosphoric acid sodium salt ≥98.0% (TLC) 1,2-Dioleoyl-sn-glycero-3-phosphoric acid is a phosphatidic acid. Phospholipids, major membrane lipids, are derived from phosphatidic acid .
1,2-Dioleoyl-sn-glycero-3-phosphoric acid regulates phospholipid metabolic genes in yeast by binding to transcriptional factor, Opi1. This binding is regulated by a rapid decrease in pH in response to glucose starvation. 1,2-Dioleoyl-sn-glycero-3-phosphoric acid acts as intracellular pH biosensor, coupling membrane biogenesis to nutrient availability .
P3400 1,2-Dipalmitoyl-rac-glycero-3-phospho(dimethylaminoethanol) ~99%  
P5911 1,2-Dipalmitoyl-rac-glycero-3-phosphocholine ~99%  
P3275 1,2-Dipalmitoyl-rac-glycero-3-phosphoethanolamine synthetic, ≥98%  
P1902 1,2-Dipalmitoyl-rac-glycero-3-phospho-L-serine ~98%  
P7022 1,2-Dipalmitoyl-sn-glycero-3-phospho(N-palmitoyl)ethanolamine ammonium salt ~99% N-Acyl phosphatidylethanolamine has been reported to accumulate in heart muscle damaged by ischemia.
P0399 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethylethanolamine ~99%  
P4329 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine ≥99% (TLC)  
P0763 1,2-Dipalmitoyl-sn-glycero-3-phosphocholine semisynthetic, ≥99%  
P1348 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine ≥97% 1,2-Dipalmitoyl-sn-glycero-3-phosphoethanolamine is a phospholipid, a lipid component in cell membrane .
P1185 1,2-Dipalmitoyl-sn-glycero-3-phospho-L-serine sodium salt ≥99% (TLC)  
42627 1,2-Dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt ≥96.0% (TLC) One of several phospholipids that serves as surfactant on lung alveolar membranes. Incorporated in small unilamellar vesicles, DPPG specifically (not other phospholipids tested) provides protection against infection by vaccinia virus.
50984 1,2-Dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥96.0% (TLC)  
P9789 1,2-Dipalmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥99% (TLC)  
P7285 1,2-Dipentadecanoyl-sn-glycero-3-phosphocholine ~99%  
55845 1,2-Distearoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥97.0% (TLC) DSPG is the most efficient phosphatidylglycerol in enhancing respiratory mucus clearance in cystic fibrosis.
D1657 1,3-Dioleoyl-2-palmitoylglycerol ≥99%  
D2157 1,3-Dipalmitoyl-2-oleoylglycerol ≥99%  
O9262 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phosphorylcholine ≥99% (TLC), waxy solid Phosphoinositide-specific phospholipase C (PI-PLC) inhibitor.
P6284 1-O-Palmityl-2-palmitoyl-rac-glycero-3-phosphocholine ~99%  
P4142 1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphocholine ≥98% (GC), ≥99% (TLC)  
L5629 1-Dodecanoyl-sn-glycero-3-phosphocholine ~99%  
L1881 1-Oleoyl-sn-glycero-3-phosphocholine synthetic, ≥99%  
L2131 1-Stearoyl-sn-glycero-3-phosphocholine ≥99%, powder 1-Stearoyl-sn-glycero-3-phosphocholine (LPC, Lyso-PC) is used in the development of drug transdermal delivery devices such as liposomes and micelles.
42566 2,3-Dipalmitoyl-sn-glycero-1-phosphocholine ≥95.0% (TLC) 2,3-Dipalmitoyl-sn-glycerol-1-phosphocholine is a major constituent of lung surfactant, a monolayer reducing lung surface tension and keeping the lung from collapsing when exhaling .
P0319 2-Arachidonoyl-1-palmitoyl-sn-glycero-3-phosphocholine 10 mg/mL in chloroform  
P1287 2-Arachidonoyl-1-stearoyl-sn-glycero-3-phosphocholine solution 10 mg/mL in chloroform  
62225 2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine ≥98.0% (10 mg phospholipid per ml CHCl3, TLC)  
51581 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-L-serine sodium salt ≥75% (TLC)  
76559 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) ammonium salt ≥97.0% (TLC)  
63371 2-Oleoyl-1-palmitoyl-sn-glycero-3-phospho-rac-(1-glycerol) sodium salt ≥98.0% (TLC)  
P3017 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine ≥95.5% (GC), ≥98% (TLC)  
42773 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine ≥99.0% (TLC)  
P5203 2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphoethanolamine lyophilized powder  
P8180 DL-α-Phosphatidylcholine, distearoyl ≥98%  
G5291 L-α-Glycerophosphorylcholine from soybean, ≥98%, powder Increases inositol phosphate formation.
P9953 L-α-Phosphatidyl-D-myo-inositol 3,4,5-triphosphate, dioctanoyl Signaling lipid; activates PDK1 (3-phosphoinositide-dependent protein kinase), which is necessary, but not sufficient, for the activation of PKB/Akt. PDK1 also phosphorylates and activates p70S6k.
P4725 L-α-Phosphatidyl-D-myo-inositol 3,4-diphosphate, dioctanoyl Activates Ca2+-insensitive PKC isotypes δ, ε, and η, activates Akt (a serine-threonine kinase also known as PKBα) by direct interaction with the Akt pleckstrin homology domain.
P5578 L-α-Phosphatidyl-D-myo-inositol 3-monophosphate, dioctanoyl  
P3953 L-α-Phosphatidyl-D-myo-inositol 3-monophosphate, dipalmitoyl  
P3584 L-α-Phosphatidyl-D-myo-inositol 4,5-diphosphate, dioctanoyl  
P7686 L-α-Phosphatidyl-D-myo-inositol 4-monophosphate, dipalmitoyl ammonium salt  
P1368 L-α-Phosphatidylinositol dipalmitoyl ammonium salt ≥98% (TLC)  
C0563   Cardiolipin sodium salt from bovine heart ≥98% (TLC), lyophilized powder Cardiolipin is a mitochondrial phospholipid that is found in mammalian tissues in low concentrations. It is often a membrane component. Inhibits cell attachment of fibronectin, vitronectin and Type I collagen.
SRE0029   Cardiolipin solution from bovine heart 4.7-5.3 mg/mL in ethanol, ≥97% (TLC), Suitable for manufacturing of diagnostic kits and reagents Cardiolipin is a mitochondrial phospholipid that is found in mammalian tissues in low concentrations. It is often a membrane component. Inhibits cell attachment of fibronectin, vitronectin and Type I collagen.
C5646   Cardiolipin solution from bovine heart ~5 mg/mL in methanol, ≥97% (TLC) Cardiolipin is a mitochondrial phospholipid that is found in mammalian tissues in low concentrations. It is often a membrane component. Inhibits cell attachment of fibronectin, vitronectin and Type I collagen.
C0256 Cytidine 5′-diphosphocholine sodium salt dihydrate ~98%, from yeast, solid Neuroprotective in situations of hypoxia and ischemia; biosynthetic intermediate of membrane phospholipids; cerebral vasodilator; inhibits PLA2 activation.
31589 Diethanolamine BioUltra, ≥99.5% (GC)  
398136 Ethanolamine ACS reagent, ≥99.0%  
90278 Triethanolamine BioUltra, ≥99.5% (GC)