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2.7: Fatty Acids

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    16246
  • Unlike monosaccharides, nucleotides, and amino acids, fatty acids are not monomers that are linked together to form much larger molecules. Although fatty acids can be linked together, for example, into triacylglycerols or phospholipids, they are not linked directly to one another, and generally no more than three in a given molecule. The fatty acids themselves are long chains of carbon atoms topped off with a carboxyl group. The length of the chain can vary, although most are between 14 and 20 carbons, and in higher order plants and animals, fatty acids with 16 and 18 carbons are the major species.

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    Figure 13. Fatty acids. (Top) Stearic acid is a fully saturated fatty acid with no carbon-carbon double bonds. (Bottom) Oleic acid is an unsaturated fatty acid.

    Due to the mechanism of synthesis, most fatty acids have an even number of carbons, although odd-numbered carbon chains can also be generated. More variety can be generated by double-bonds between the carbons. Fatty acid chains with no double bonds are saturated, because each carbon is saturated with as many bonded hydrogen atoms as possible. Fatty acid chains with double bonds are unsaturated (Figure 13). Those with more than one double bond are called polyunsaturated. The fatty acids in eukaryotic cells are nearly evenly divided between saturated and unsaturated types, and many of the latter may be polyunsaturated. In prokaryotes, polyunsaturation is rare, but other modifications such as branching and cyclization are more common than in eukaryotes. A table of common fatty acids is shown below.

    Myristic Acid 14:0 (14 carbons, no double bonds
    Palmitic Acid 16:0
    Stearic Acid 18:0
    Arachidic Acid 20:0
    Palmitoleic Acid 16:1
    Oleic Acid 18:1
    Linoleic Acid 18:2
    Arachidonic Acid 2:4

    There are significant physical differences between the saturated and unsaturated fatty acids due simply to the geometry of the double-bonded carbons. A saturated fatty acid is very flexible with free rotation around all of its C-C bonds. The usual linear diagrams and formulas depicting saturated fatty acids also serve to explain the ability of saturated fatty acids to pack tightly together, with very little intervening space. Unsaturated fatty acids, on the other hand are unable to pack as tightly because of the rotational constraint impoarted by the double bond. The carbons cannot rotate around the double bond, so there is now a “kink” in the chain. Generally, double-bonded carbons in fatty acids are in the cis- configuration, introducing a 30-degree bend in the structure.

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    Figure 14. Triglycerides. These lipids are formed by conjugation of a glycerol to three fatty acyl chains through ester bonds from each glycerol oxygen.

    Fatty acids inside cells are usually parts of larger molecules, rather than free acids. Some of the most common lipids derived from fatty acids are triacylglycerols, phosphoglycerides, and sphingolipids. Triacylglycerols, as the name implies, is three fatty acid (acyl) chains connected to a glycerol molecule by ester bonds (Figure 14). Triacylglycerols, also known as triglycerides, may have fatty acids of the same (simple triacylglycerols) or varying types (mixed triacylglycerols). Mixtures of these are the primary long-term energy storage molecules for most organisms. Although they may be referred to colloquially as fats or oils, the only real difference is the degree of saturation of their constituent fatty acids. Mixtures with higher percentages of saturated fatty acids have a higher melting point and if they are solid at room temperature, they are referred to as fats. Triacylglycerol mixtures remaining liquid at room temperature are oils.

    In human medicine, a common test for heart disease risk factors is measurement of triglyceride levels in the blood. Although various cell types can make and use triglycerides, most of the triglycerides in people are concentrated in the adipose tissue, which is made up of adipocytes, or fat cells, though liver is also a significant fat store. These cells have specialized to carry fat globules that take up most of the volume of the cell. When triglyceride levels in the blood are high, it means that fat is being produced or ingested faster than it can be taken up by the adipocytes.

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    Figure 15. A phospholipid: the glycerol backbone (red) connects to two fatty acids and to a phosphate and polar head group.

    Phospholipids (also called phosphoglycerides or glycerophospholipids), are also based on attachment of fatty acids to glycerol. However, instead of three fatty acyl tails, there are only two, and in the third position is a phosphate group (Figure 15). The phosphate group also attaches to a “head group” . The identity of the head group names the molecule, along with the fatty acyl tails. In the example figure, 1-stearoyl refers to the stearic acid on the 1-carbon of the glycerol backbone; 2-palmitoyl refers to the palmitic acid on the 2-carbon of the glycerol, and phosphatidylethanolamine refers to the phosphate group and its attached ethanolamine, that are linked to the glycerol 3-carbon. Because of the negatively-charge phosphate group, and a head group that is often polar or charged, phospholipids are amphipathic - carrying a strong hydrophobic character in the two fatty acyl tails, and a strong hydrophilic character in the head group. This amphipathicity is crucial in the role of phospholipids as the primary component of cellular membranes.

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    Figure 16. Sphingolipids are based on the amino alcohol, sphingosine (A). Ceramides have a fatty acid tail attached, and a ceramide with a phosphocholine head group is a sphingomyelin (B). If the head group is a sugar, then the molecule is a cerebroside. (C)

    Sphingolipids (Figure 16) are also important constituents of membranes, and are based not upon a glycerol backbone, but on the amino alcohol, sphingosine (or dihydrosphingosine). There are four major types of sphingolipids: ceramides, sphingomyelins, cerebrosides, and gangliosides. Ceramides are sphingosine molecules with a fatty acid tail attached to the amino group. Sphingomyelins are ceramides in which a phosphocholine or phosphoethanolamine are attached to the 1-carbon. Cerebrosides and gangliosides are glycolipids - they have a sugar or sugars, respectively, attached to the 1-carbon of a ceramide. The oligosaccharides attached to gangliosides all contain at least one sialic acid residue. In additional to being a structural component of the cell membrane, gangliosides are particular important in cell to cell recognition.

    Lipids are vaguely defined as biological compounds that are insoluble in water but are soluble in organic solvents such as methanol or chloroform. This includes the fatty acid derivatives listed above, and it includes the final topic for this chapter, cholesterol. Cholesterol (Figure 17) is the major biological derivative of cyclopentanoperhydrophenanthrene, a saturated hydrocarbon consisting of four fused ring formations. It is an important component of plasma membranes in animal cells, and is also the metabolic precursor to steroid hormones, such as cortisol or b-estradiol. Plant cells have little if any cholesterol, but other sterols like stigmasterol are present. Similarly, fungi have their particular sterols. However, prokaryotes do not, for the most part, contain any sterol molecules.

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    Figure 17. Cholesterol is an important lipid both as a membrane component and as a steroid precursor.