Garrett and Grisham, Biochemistry, Third Edition AMINO ACIDS The building blocks for proteins.
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Transcript of Garrett and Grisham, Biochemistry, Third Edition Chapter 8 Lipids Biochemistry by Reginald Garrett...
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Garrett and Grisham, Biochemistry, Third Edition
Chapter 8
Lipids
Biochemistry
by
Reginald Garrett and Charles Grisham
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Garrett and Grisham, Biochemistry, Third Edition
Essential Question
• What is the structure, chemistry, and biological function of lipids?
• Lipids – low solubility in water and high solubility in nonpolar solvents.
• The hydrophobic nature of lipids allows membranes to act as effective barriers to more polar molecules.
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Garrett and Grisham, Biochemistry, Third Edition
Outline• What Is the Structure and Chemistry of Fatty Acids?• What Is the Structure and Chemistry of
Triacylglycerols? • What is the Structure and Chemistry of
Glycerophospholipids?• What Are Sphingolipids, and How Are They Important
for Higher Animals? • What Are Waxes, and How Are They Used?• What Are Terpenes, and What Is Their Relevance to
Biological Systems?• What Are Steriods, and What Are Their Cellular
Functions?
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Garrett and Grisham, Biochemistry, Third Edition
Classes of Lipids
All biological lipids are amphipathic (containing both polar and nonpolar
groups).
• Fatty acids • Triacylglycerols • Glycerophospholipids • Sphingolipids • Waxes • Isoprene-based lipids (including steroids)
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Garrett and Grisham, Biochemistry, Third Edition
8.1 - Fatty acids
Know the common names and structures for fatty acids up to 20 carbons long
• Saturated – Lauric acid (12 C) – Myristic acid (14 C) – Palmitic acid (16 C) – Stearic acid (18 C) – Arachidic acid (20 C)
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Garrett and Grisham, Biochemistry, Third Edition
Fatty acids - II
• Unsaturated fatty acids
– Palmitoleic acid (16:1)
– Oleic acid (18:1)
– Linoleic acid (18:2) -Linolenic acid (18:3) -Linolenic acid (18:3)
– Arachidonic acid (20:4)
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Garrett and Grisham, Biochemistry, Third Edition
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Garrett and Grisham, Biochemistry, Third Edition
Fatty acids - III
Structural consequences of unsaturation
• Saturated chains pack tightly and form more rigid, organized aggregates (i.e., membranes)
• Unsaturated chains bend and pack in a less ordered way, with greater potential for motion
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Garrett and Grisham, Biochemistry, Third Edition
Source Lauric & Myristic Palmitic Stearic Oleic Linoleic
Beef 5 24-32 20-25 37-43 2-3Milk 25 12 33 3Coconut 74 10 2 7Corn 8-12 3-4 19-49 34-62Olive 9 2 84 4Palm 39 4 40 8Safflower 6 3 13 78Soybean 9 6 20 52Sunflower 6 1 21 66
Fatty acids in Food: saturated vs. unsaturated
Fatty acid compositions of some dietary lipids
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Garrett and Grisham, Biochemistry, Third Edition
8.2 - Triacylglycerols
Also called triglycerides
• A major energy source for many organisms
• Why?
– Most reduced form of carbon in nature
– No solvation needed
– Efficient packing
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Garrett and Grisham, Biochemistry, Third Edition
Triacylglycerols - II
Other advantages accrue to users of triacylglycerols :
• Insulation • Energy without nitrogen • Metabolic water
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Garrett and Grisham, Biochemistry, Third Edition
8.3 - Glycerophospholipids
Glycerophospholipids are phospholipids but not necessarily vice versa.
• Know the names and structures in Figure 8.6 • Understand the prochirality of glycerol • Remember that, if phospholipid contains
unsaturation, it is at the 2-position.
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Garrett and Grisham, Biochemistry, Third Edition
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Garrett and Grisham, Biochemistry, Third Edition
Ether Glycerophospholipids
An ether instead of an acyl group at C-1
•Figure 8.8
1-alkyl 2-acyl-phosphatidylethanolamine (an ether glycerophospholipid)
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Garrett and Grisham, Biochemistry, Third Edition
Ether Glycerophospholipids• Platelet activating factor (PAF) is an ether glycerophospholipid.
• PAF is a potent biochemical signal molecule • Note the short (acetate) fatty acyl chain at the C-2 position in PAF.• PAF is much more water soluble, functions as a soluble messenger in signal transduction.
Figure 8.9 1-alkyl 2-acyl-phosphatidylcholine (PAF)
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Garrett and Grisham, Biochemistry, Third Edition
8.4 – Sphingolipids 神經鞘脂質
Base structure is sphingosine.
•Sphingosine is an 18-carbon amino alcohol. •Ceramides are amide linkages of fatty acids to the nitrogen of sphingosine. •Glycosphingolipids are ceramides with one or more sugars in beta-glycosidic linkage at the 1-hydroxyl group.
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Garrett and Grisham, Biochemistry, Third Edition
SphingolipidsBase structure is sphingosine.
•Sphingosine is an 18-carbon amino alcohol. •Ceramides (神經醯胺 ) are amide linkages of fatty acids to the nitrogen of sphingosine. •Glycosphingolipids are ceramides with one or more sugars in beta-glycosidic linkage at the 1-hydroxyl group.
Figure 8.11 Formation of an amide linkage between a fatty acid and sphingosine produces a ceramide.
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Garrett and Grisham, Biochemistry, Third Edition
Sphingolipids
Backbone of sphingosine: 18-carbon amino alcohol with C-C trans double bond
Ceramide: sphingosine with fatty acid in amide linkage Sphingomyelins: alcohol esterified to phosphoceramide
Choline Ethanolamine
Glycosphingolipids: ceramide with sugars in -glycosidic linkage
Cerebroside: Sugar is glucose or galactose. Sulfatide: Sugar is galactose with sulfate esterified at carbon 3 of galactose. Gangliosides: ceramide with three or more sugars including sialic acid
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Garrett and Grisham, Biochemistry, Third Edition
8.5 - Waxes
Esters of long-chain alcohols with long-chain fatty acids
• Highly insoluble • Animal skin and fur are wax-coated • Leaves of many plants • Bird feathers
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Garrett and Grisham, Biochemistry, Third Edition
8.5 WaxesEsters of long-chain alcohols with long-chain
fatty acids
• highly insoluble • Animal skin and fur are wax-coated .• leaves of many plants • bird feathers
Figure 8.15 An example of a wax. Oleoyl alcohol is esterified to stearic acid in this case.
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Garrett and Grisham, Biochemistry, Third Edition
8.6 - Terpenes
Based on the isoprene structure
• Know nomenclature • Understand linkage modes (Figure 8.16) • See structures in Figure 8.17 • All sterols (including cholesterol) are terpene-
based molecules. • Steroid hormones are terpene-based.
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Garrett and Grisham, Biochemistry, Third Edition
8.6 Terpenes
Based on the isoprene structure
• Know nomenclature • All sterols (including cholesterol) are
terpene-based molecules. • Steroid hormones are terpene-based.
Figure 8.16
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Garrett and Grisham, Biochemistry, Third Edition
8.7 - Steroids
• Based on a core structure consisting of three 6-membered rings and one 5-membered ring, all fused together.
• Cholesterol is the most common steroid in animals and precursor for all other steroids in animals.
• Steroid hormones serve many functions in animals - including salt balance, metabolic function and sexual function.
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Garrett and Grisham, Biochemistry, Third Edition
An A-B cis steroid
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Figure 8.19 The structure of cholesterol, shown with steroid ring designations and carbon numbering.