POPC

Last updated
POPC
1-palmitoyl-2-oleoylphosphatidylcholine.svg
Names
Systematic IUPAC name
(2R)-3-(Hexadecanoyloxy)-2-{[(9Z)-octadec-9-enoyl]oxy}propyl 2-(trimethylazaniumyl)ethyl phosphate
Other names
1-Palmitoyl-2-oleoylphosphatidylcholine, palmitoyloleoylphosphatidylcholine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.043.673 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1 Yes check.svgY
    Key: WTJKGGKOPKCXLL-VYOBOKEXSA-N Yes check.svgY
  • CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)([O-])OCC[N+](C)(C)C)OC(=O)CCCCCCC/C=C\CCCCCCCC
Properties
C42H82NO8P
Molar mass 760.091 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

POPC (1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine) is a phosphatidylcholine. It is a diacylglycerol phospholipid. It is an important phospholipid for biophysical experiments and has been used to study various subjects such as lipid rafts. POPC is also used in systems mimicking the cell membrane such as Nanodiscs. [1] It is available commercially [2] and is naturally present in eukaryotic cell membranes.

Related Research Articles

<span class="mw-page-title-main">Sphingomyelin</span> Class of chemical compounds

Sphingomyelin is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath that surrounds some nerve cell axons. It usually consists of phosphocholine and ceramide, or a phosphoethanolamine head group; therefore, sphingomyelins can also be classified as sphingophospholipids. In humans, SPH represents ~85% of all sphingolipids, and typically make up 10–20 mol % of plasma membrane lipids.

<span class="mw-page-title-main">Glycerophospholipid</span> Class of lipids

Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes. Two major classes are known: those for bacteria and eukaryotes and a separate family for archaea.

Platelet-activating factor, also known as PAF, PAF-acether or AGEPC (acetyl-glyceryl-ether-phosphorylcholine), is a potent phospholipid activator and mediator of many leukocyte functions, platelet aggregation and degranulation, inflammation, and anaphylaxis. It is also involved in changes to vascular permeability, the oxidative burst, chemotaxis of leukocytes, as well as augmentation of arachidonic acid metabolism in phagocytes.

<span class="mw-page-title-main">Ether lipid</span>

In an organic chemistry general sense, an ether lipid implies an ether bridge between an alkyl group and an unspecified alkyl or aryl group, not necessarily glycerol. If glycerol is involved, the compound is called a glyceryl ether, which may take the form of an alkylglycerol, an alkyl acyl glycerol, or in combination with a phosphatide group, a phospholipid.

In enzymology, a phosphatidylcholine desaturase (EC 1.14.19.22, previously EC 1.3.1.35) is an enzyme that catalyzes the chemical reaction

In enzymology, an alkenylglycerophosphocholine hydrolase (EC 3.3.2.2) is an enzyme that catalyzes the chemical reaction

The enzyme 1-alkyl-2-acetylglycerophosphocholine esterase (EC 3.1.1.47) catalyzes the reaction

In enzymology, a 1-alkylglycerophosphocholine O-acetyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a 1-alkylglycerophosphocholine O-acyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a 2-acylglycerophosphocholine O-acyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a glycerophospholipid acyltransferase (CoA-dependent) is an enzyme that catalyzes the chemical reaction

In the field of enzymology, a glycerophospholipid arachidonoyl-transferase (CoA-independent) is an enzyme that catalyzes the chemical reaction:

In enzymology, a platelet-activating factor acetyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Diacylglycerol cholinephosphotransferase</span>

In enzymology, a diacylglycerol cholinephosphotransferase is an enzyme that catalyzes the chemical reaction

Archaeol is composed of two phytanyl chains linked to the sn-2 and sn-3 positions of glycerol. As its phosphate ester, it is a common component of the membranes of archaea.

<span class="mw-page-title-main">Nanodisc</span> Synthetic model membrane system

A nanodisc is a synthetic model membrane system which assists in the study of membrane proteins. Nanodiscs are discoidal proteins in which a lipid bilayer is surrounded by molecules that are amphipathic molecules including proteins, peptides, and synthetic polymers. It is composed of a lipid bilayer of phospholipids with the hydrophobic edge screened by two amphipathic proteins. These proteins are called membrane scaffolding proteins (MSP) and align in double belt formation. Nanodiscs are structurally very similar to discoidal high-density lipoproteins (HDL) and the MSPs are modified versions of apolipoprotein A1 (apoA1), the main constituent in HDL. Nanodiscs are useful in the study of membrane proteins because they can solubilise and stabilise membrane proteins and represent a more native environment than liposomes, detergent micelles, bicelles and amphipols.

A model lipid bilayer is any bilayer assembled in vitro, as opposed to the bilayer of natural cell membranes or covering various sub-cellular structures like the nucleus. They are used to study the fundamental properties of biological membranes in a simplified and well-controlled environment, and increasingly in bottom-up synthetic biology for the construction of artificial cells. A model bilayer can be made with either synthetic or natural lipids. The simplest model systems contain only a single pure synthetic lipid. More physiologically relevant model bilayers can be made with mixtures of several synthetic or natural lipids.

<span class="mw-page-title-main">Ethanol-induced non-lamellar phases in phospholipids</span>

The presence of ethanol can lead to the formations of non-lamellar phases also known as non-bilayer phases. Ethanol has been recognized as being an excellent solvent in an aqueous solution for inducing non-lamellar phases in phospholipids. The formation of non-lamellar phases in phospholipids is not completely understood, but it is significant that this amphiphilic molecule is capable of doing so. The formation of non-lamellar phases is significant in biomedical studies which include drug delivery, the transport of polar and non-polar ions using solvents capable of penetrating the biomembrane, increasing the elasticity of the biomembrane when it is being disrupted by unwanted substances and functioning as a channel or transporter of biomaterial.

A lysophosphatidylethanolamine (LPE) is a chemical compound derived from a phosphatidylethanolamine, which is typical of cell membranes. LPE results from partial hydrolysis of phosphatidylethanolamine, which removes one of the fatty acid groups. The hydrolysis is generally the result of the enzymatic action of phospholipase A2. LPE can be used in agricultural use to regulate plant growth such as color increase, sugar content increase, plant health increase, and storability increase without side effect.

<span class="mw-page-title-main">1-Lysophosphatidylcholine</span>

2-acyl-sn-glycero-3-phosphocholines are a class of phospholipids that are intermediates in the metabolism of lipids. Because they result from the hydrolysis of an acyl group from the sn-1 position of phosphatidylcholine, they are also called 1-lysophosphatidylcholine. The synthesis of phosphatidylcholines with specific fatty acids occurs through the synthesis of 1-lysoPC. The formation of various other lipids generates 1-lysoPC as a by-product.

References

  1. Stephen G. Sligar. "Nanodisc Technology: Soluble Lipid Bilayer Systems for Structural and Functional Studies of Membrane Proteins".
  2. "1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine (CHEBI:73001)". www.ebi.ac.uk. Retrieved 2023-11-12.