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Phospholipid

Twoad group of the molecule, highlighted in red.
The U indicates the uncharged hydrophobic portion of the molecule, highlighted in blue.

Phosphatidyl choline is the major component of lecithin. It is also a source for choline in the synthesis of acetylcholine in cholinergic neurons.

Phospholipids are a class of lipids, and a major component of all biological membranes, along with glycolipids, cholesterol and proteins. Understanding of the aggregation properties of these molecules is known as lipid polymorphism and forms part of current academic research.

They are built upon to a nitrogen-containing alcohol like ethanolamine or an organic compound such as choline. The "head" with hydrophilic built, adopts a lipophilic characteristic in the polar phospholipid area. The "tails" however are non-polar and they adopt a characteristic of hydrophobic- (being repelled by water). In its simplest form, a phospholipid is composed of one glycerol bonded to two fatty acids and one phosphate group.

In cell membranes, phosphoglycerides are the more common of the two phospholipids. 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.

In phosphoglyceride synthesis, phosphatidates must be activated first. Phospholipids can be formed from an activated diacylglycerol or an activated alcohol.

• Phosphatidyl serine and phosphatidyl inositol are formed from a phosphoester linkage between the hydroxyl of an alcohol (serine or inositol) and cytidine diphosphodiacylglycerol (CDP-diacylglycerol).

• In animals, plants and yeast 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. In bacteria, the serine moiety of phosphatidyl serine is decarboxylated to give phospatidyl ethanolamine.

• In mammals, phosphatidyl choline can be synthesized via two separate pathways; a series of reactions similar to phosphatidyl ethanolamine synthesis, and the methylation of phosphatidyl ethanolamine, which is catalyzed by phosphatidyl ethanolamine methyltransferase, an enzyme produced in the liver.

Phosphatidyl ethanolamine is the major component of cephalin.

Phosphatidyl inositol

Phosphatidyl serine

Diphosphatidyl glycerol (Cardiolipin)

Sphingomyelin (Red:Phosphatidyl choline, Blue:Acyl CoA)

The backbone of sphingomyelin is sphingosine, an amino alcohol formed from palmitate and serine. The amino terminal is acylated with a long-chain acyl CoA to yield ceramide. Subsequent substitution of the terminal hydroxyl group by phosphatidyl choline forms sphingomyelin.

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.

Due to its polar nature, the head of a phospholipid is hydrophilic (attracted to water); the lipophilic (or often known as hydrophobic) tails are not attracted to water. When placed in water, phospholipids form one of a number of lipid phases. In biological systems this is restricted to bilayers, in which the lipophilic tails line up against one another, forming a membrane with hydrophilic heads on both sides facing 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.

This membrane is partially permeable, capable of elastic movement, and has fluid properties, in which embedded proteins (integral or peripheral proteins) and phospholipid molecules are able to move laterally. Such movement can be described by the Fluid Mosaic Model, that 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. Cholesterol contributes to membrane fluidity by hindering the packing together of phospholipids. However, this model has now been superseded, as through the study of lipid polymorphism it is now known that the behaviour of lipids under physiological (and other) conditions is not simple.

• Alkylphosphocholines
• Antiphospholipid syndrome
• Biochemistry
• Lipid
• Lipid bilayer (e.g., Cell membrane)
• Polymorphism (biophysics)

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