A typical biomembrane is assembled from phosphoglyc-erides, sphingolipids, and steroids. All three classes of lipids are amphipathic molecules having a polar (hydrophilic) head group and hydrophobic tail. The hydrophobic effect and van der Waals interactions, discussed in Chapter 2, cause the tail groups to self-associate into a bilayer with the polar head groups oriented toward water (see Figure 5-2). Although the common membrane lipids have this amphipathic character in common, they differ in their chemical structures, abundance, and functions in the membrane.
Phosphoglycerides, the most abundant class of lipids in most membranes, are derivatives of glycerol 3-phosphate (Figure 5-5a). A typical phosphoglyceride molecule consists of a hydrophobic tail composed of two fatty acyl chains es-terified to the two hydroxyl groups in glycerol phosphate and a polar head group attached to the phosphate group. The two fatty acyl chains may differ in the number of carbons that they contain (commonly 16 or 18) and their degree of saturation (0, 1, or 2 double bonds). A phosphogyceride is classified according to the nature of its head group. In phos-phatidylcholines, the most abundant phospholipids in the plasma membrane, the head group consists of choline, a positively charged alcohol, esterified to the negatively charged phosphate. In other phosphoglycerides, an OH-containing molecule such as ethanolamine, serine, and the sugar derivative inositol is linked to the phosphate group. The negatively charged phosphate group and the positively charged groups or the hydroxyl groups on the head group interact strongly with water.
The plasmalogens are a group of phosphoglycerides that contain one fatty acyl chain, attached to glycerol by an ester linkage, and one long hydrocarbon chain, attached to glyc-erol by an ether linkage (C—O—C). These molecules constitute about 20 percent of the total phosphoglyceride content in humans. Their abundance varies among tissues and species but is especially high in human brain and heart tissue. The additional chemical stability of the ether linkage in plasmalogens or the subtle differences in their three-dimensional structure compared with that of other phos-phoglycerides may have as-yet unrecognized physiologic significance.
A second class of membrane lipid is the sphingolipids. All of these compounds are derived from sphingosine, an amino alcohol with a long hydrocarbon chain, and contain a long-chain fatty acid attached to the sphingosine amino group. In sphingomyelin, the most abundant sphingolipid, phosphocholine is attached to the terminal hydroxyl group of sphingosine (Figure 5-5b). Thus sphingomyelin is a phospholipid, and its overall structure is quite similar to that of phosphatidylcholine. Other sphingolipids are amphipathic glycolipids whose polar head groups are sugars. Glucosyl-cerebroside, the simplest glycosphingolipid, contains a single glucose unit attached to sphingosine. In the complex gly-cosphingolipids called gangliosides, one or two branched sugar chains containing sialic acid groups are attached to
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