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Encyclopedia > Phospholipid
Phospholipid
Phospholipid
Two schematic representations of a phospholipid.The P represents the polar hydrophilic head group of the molecule, highlighted in red.The U indicates the uncharged hydrophobic portion of the molecule, highlighted in blue.
Two schematic representations of a phospholipid.
The P represents the polar hydrophilic head group of the molecule, highlighted in red.
The U indicates the uncharged hydrophobic portion of the molecule, highlighted in blue.

Phospholipids are a class of lipids, and a major component of all biological membranes, along with glycolipids and cholesterol. Image File history File links No higher resolution available. ... Image File history File links No higher resolution available. ... moving over from nupedia File links The following pages link to this file: Phospholipid Categories: GFDL images ... moving over from nupedia File links The following pages link to this file: Phospholipid Categories: GFDL images ... Figure 1: Basic lipid structure. ... A biological membrane or biomembrane is an enclosing or separating tissue which acts as a barrier within or around a cell. ... Glycolipids are carbohydrate-attached lipids. ... Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. ...

Contents

Components

They are built upon one of two kinds of backbones:

The following components are attached to the carbons on the backbone: Glycerol, also well known as glycerin and glycerine, and less commonly as propane-1,2,3-triol, 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. ... Sphingosine is a compound that forms a primary part of the sphingolipids, a class of cell membrane lipids which includes sphingomyelin, an important phospholipid. ... Sphingomyelin is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. ...

In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Above is a ball-and-stick model of the inorganic hydrogenphosphate anion (HPO42−). Colour coding: P (orange); O (red); H (white). ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Atomic mass 14. ... Functional group of an alcohol molecule. ... Ethanolamine, or 2-Amino ethanol, is a toxic flammable corrosive colorless viscous liquid with an odor similar to ammonia. ...

Types

Phosphoglycerides

Phosphatidyl choline. Phosphatidyl choline is the major component of lecithin. It is also a source for choline in the synthesis of acetylcholine in cholinergic neurons.
Phosphatidyl choline. Phosphatidyl choline is the major component of lecithin. It is also a source for choline in the synthesis of acetylcholine in cholinergic neurons.
Phosphatidyl ethanolamine. Phosphatidyl ethanolamine is the major component of cephalin.
Phosphatidyl ethanolamine. Phosphatidyl ethanolamine is the major component of cephalin.
Diphosphatidyl glycerol (Cardiolipin)

In phosphoglycerides, the carboxyl group of each fatty acid is esterified to the hydroxyl groups on carbon-1 and carbon-2 of the glycerol molecule. The phosphate group is attached to carbon-3 by an ester link. This molecule, known as a phosphatidate, is present in small quantities in membranes, but is also a precursor for the other phosphoglycerides. Image File history File links Structural formula of phosphatidyl choline (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: Choline) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of phosphatidyl choline (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: Choline) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Two schematic representations of a phospholipid. ... Phosphatidylcholine, a phospholipid in lecithin. ... // Choline is a nutrient, essential for cardiovascular and brain function, and for cellular membrane composition and repair. ... Image File history File links Structural formula of phosphatidyl ethanolamine (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: ethanolamine) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of phosphatidyl ethanolamine (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: ethanolamine) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Two schematic representations of a phospholipid. ... Cephalin is a phospholipid, which is a lipid derivative. ... Image File history File links Structural formula of phosphatidyl inositol (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: inositol) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of phosphatidyl inositol (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: inositol) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Phosphatidylinositol (PI), a phospholipid that is located in the plasma membrane. ... Image File history File links Structural formula of phosphatidyl serine (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: serine) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of phosphatidyl serine (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: serine) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Phosphatidylserine is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes. ... Image File history File links Structural formula of Diphosphatidyl glycerol (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: Glycerol) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of Diphosphatidyl glycerol (Blue/Green: Fatty acid, Black: Glycerol backbone, Red: phosphate, Purple: Glycerol) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Cardiolipin Cardiolipin (alternate image) Cardiolipin (bisphosphatidyl glycerol) is an important component of the inner mitochondrial membrane, where it constitutes about 20% of the total lipid. ... A carboxyl or carboxylic group is a functional group consisting of a carbon atom and an oxygen atom doubly bonded to each other. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... Phosphatidate (red: phosphate group, blue & green: fatty acid) Phosphatidates are biochemical compounds that consist of a glycerol backbone, with a (usually) saturated fatty acid bonded to carbon-1, a (usually) unsaturated fatty acid bonded to carbon-2 and a phosphate group bonded to carbon-3. ...


In phosphoglyceride synthesis, phosphatidates must be activated first. Phospholipids can be formed from an activated diacylglycerol or an activated alcohol. Phosphatidate (red: phosphate group, blue & green: fatty acid) Phosphatidates are biochemical compounds that consist of a glycerol backbone, with a (usually) saturated fatty acid bonded to carbon-1, a (usually) unsaturated fatty acid bonded to carbon-2 and a phosphate group bonded to carbon-3. ... Diacylglycerol (DAG) is a second messenger molecule made by phospholipase C (a membrane-bound enzyme), together with inositol triphosphate. ...

  • In the synthesis of phospatidyl ethanolamine, the alcohol is phosphorylated by ATP first, and subsequently reacts with cytidine triphosphate (CTP) to form the activated alcohol (CDP-ethanolamine). The alcohol then reacts with a diacylglycerol to form the final product.

Phosphatidylserine is a phospholipid nutrient found in fish, green leafy vegetables, soybeans and rice, and is essential for the normal functioning of neuronal cell membranes. ... Phosphatidylinositol (PI), a phospholipid that is located in the plasma membrane. ... Diagram of phosphodiester bonds between nucleotides A phosphodiester bond is a group of strong covalent bonds between the phosphorus atom in a phosphate group and two other molecules over two ester bonds. ... Serine is one of the 20 natural amino acids. ... Inositol, or cis-1,2,3,5-trans-4,6-cyclohexanehexol, is a cyclic polyalcohol that plays an important role as a second messenger in a cell, in the form of inositol phosphates. ... Phosphatidylethanolamine is a lipid found in biological membranes. ... Adenosine 5-triphosphate (ATP) is a multifunctional nucleotide that is most important as a molecular currency of intracellular energy transfer. ... Two schematic representations of a phospholipid. ... Phosphatidyl ethanolamine methyltransferase is an enzyme involved in the synthesis of phosphatidylcholine. ... The liver is an organ in some animals, including vertebrates (and therefore humans). ...

Sphingomyelin

The backbone of sphingomyelin is sphingosine, an amino alcohol formed from palmitate and serine. The amino terminal is acylated with a by a long-chain acyl CoA to yield ceramide. Subsequent substitution of the terminal hydroxyl group by phosphatidyl choline forms sphingomyelin. Image File history File links Structural formula of sphingomyelin (Red: Phosphatidyl choline, Blue: Acyl CoA, Black: Sphingosine backbone) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Image File history File links Structural formula of sphingomyelin (Red: Phosphatidyl choline, Blue: Acyl CoA, Black: Sphingosine backbone) File history Legend: (cur) = this is the current file, (del) = delete this old version, (rev) = revert to this old version. ... Sphingomyelin is a type of sphingolipid found in animal cell membranes, especially in the membranous myelin sheath which surrounds some nerve cell axons. ... Two schematic representations of a phospholipid. ... Acyl CoA is a coenzyme involved in the metabolism of fatty acids. ... Sphingosine is a compound that forms a primary part of the sphingolipids, a class of cell membrane lipids which includes sphingomyelin, an important phospholipid. ... Definition: Compounds possessing both a hydroxyl (-OH) and an amino group (-NH2). ... It has been suggested that this article or section be merged into Palmitic acid. ... Serine is one of the 20 natural amino acids. ... In chemistry, acylation is the process of adding an acyl group to a compound. ... Ceramides are a family of lipid molecules. ...


Sphingomyelin is also present in all eukaryotic cell membranes, especially the plasma membrane, and is particularly concentrated in the nervous system because sphingomyelin is a major component of myelin, the fatty insulation wrapped around nerve cells by Schwann cells or oligodendrocytes. Multiple sclerosis is a disease characterised by deterioration of the myelin sheath, leading to impairment of nervous conduction. Kingdoms Animalia - Animals Fungi Plantae - Plants Protista Animals, plants, fungi, and protists are eukaryotes (IPA: ), organisms with a complex cell or cells, in which the genetic material is organized into a membrane-bound nucleus or nuclei. ... Drawing of the structure of cork as it appeared under the microscope to Robert Hooke from Micrographia which is the origin of the word cell. Cells in culture, stained for keratin (red) and DNA (green). ... Illustration of a cell membrane The cell membrane, also called the plasma membrane or plasmalemma, is a semipermeable lipid layer surrounding the cytoplasm of all living cells. ... In neuroscience, myelin is an electrically insulating phospholipid layer that surrounds the axons of many neurons. ... Schwann cells are a variety of neuroglia that wrap around axons in the peripheral nervous system, forming the myelin sheath. ... These are a variety of neuroglias that wrap around neurons in Central Nervous System to for the mtolin sheath, increasing impulse speed. ...


Amphipathic character

Due to its polar nature, the head of a phospholipid is hydrophilic (attracted to water); the nonpolar tails are hydrophobic (not attracted to water). When placed in water, phospholipids form a bilayer, where the hydrophobic tails line up against each other, forming a membrane with hydrophilic heads on both sides extending out into the water. This allows it to form liposomes spontaneously, or small lipid vesicles, which can then be used to transport materials into living organisms and study diffusion rates into or out of a cell membrane. The adjective hydrophilic describes something that likes water (from Greek hydros = water; philos = friend). ... Impact of a drop of water. ... In chemistry, hydrophobic or lipophilic species, or hydrophobes, tend to be electrically neutral and nonpolar, and thus prefer other neutral and nonpolar solvents or molecular environments. ... A bilayer is a closely packed double layer of atoms or molecules. ... A liposome is a spherical vesicle with a membrane composed of a phospholipid bilayer used to deliver drugs or genetic material into a cell. ... In cell biology, a vesicle is a relatively small and enclosed compartment, separated from the cytosol by at least one lipid bilayer. ...


This membrane is partially permeable, very flexible, and has fluid properties, in which embedded proteins and phospholipid molecules are constantly moving laterally across the membrane because of the forces generated by their vibrations. Such movement can be described by the Fluid Mosaic Model, which describes the membrane as a "mosaic" of lipid molecules that act as a solvent for all the substances and proteins within it, so proteins and lipid molecules are then free to diffuse laterally through the lipid matrix and migrate over the membrane. Any membrane media that allows passage of small particles, as well as liquids and gasses from one side of the membrane to the other, is called permeable. ... A fluid is defined as a substance that continually deforms (flows) under an applied shear stress regardless of the magnitude of the applied stress. ... Drawing of a cell membrane A component of every biological cell, the cell membrane (or plasma membrane) is a thin and structured bilayer of phospholipid and protein molecules that encapsulate the cell. ...


See also

Alkylphosphocholines are Phospholipid-like molecules that have been synthesised, which have remarkable biological and therapeutic activities. ... This article, image, template or category should belong in one or more categories. ... Biochemistry is the study of the chemical processes and transformations in living organisms. ... Lipids are a class of hydrocarbon-containing organic compounds. ... A diagonal molecular slab from the DPPC lipid bilayer simulation1; color scheme: PO4 - green, N(CH3)3 - violet, water - blue, terminal CH3 - yellow, O - red, glycol C - brown, chain C - grey. ... Illustration of a cell membrane The cell membrane, also called the plasma membrane or plasmalemma, is a semipermeable lipid layer surrounding the cytoplasm of all living cells. ...

References

  1. Berg, J.M., J.L. Tymoczko, and L. Stryer, Biochemistry. 5th ed. 2002, New York: W.H. Freeman. xxxviii, 974, [976] (various pagings)

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