Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Chapter 8 Lipids to accompany Biochemistry, 2/e by Reginald Garrett and.

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Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Chapter 8 Lipids to accompany Biochemistry, 2/e by Reginald Garrett and Charles Grisham All rights reserved. Requests for permission to make copies of any part of the work should be mailed to: Permissions Department, Harcourt Brace & Company, 6277 Sea Harbor Drive, Orlando, Florida

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Outline 8.1 Fatty Acids 8.2 Triacylglycerols 8.3 Glycerophospholipids 8.4 Sphingolipids 8.5 Waxes 8.6 Terpenes 8.7 Steroids

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Classes of Lipids All biological lipids are amphipathic Fatty acids Triacylglycerols Glycerophospholipids Sphingolipids Waxes Isoprene-based lipids (including steroids)

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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)

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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)

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Triacylglycerols - II Other advantages accrue to users of triacylglycerols Insulation Energy without nitrogen Metabolic water

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company Ether Glycerophospholipids An ether instead of an acyl group at C-1 See Figure 8.8 Plasmalogens are ether glycerophospholipids in which the alkyl chain is unsaturated

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 8.4 Sphingolipids 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 8.4 Sphingolipids Glycosphingolipids with one sugar are cerebrosides Gangliosides - ceramides with 3 or more sugars, one of which is a sialic acid

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company 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

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company

Biochemistry 2/e - Garrett & Grisham Copyright © 1999 by Harcourt Brace & Company