Chapter 11- Outline.ppt
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1、11-1,Chapter 11: Outline,Lipid Classes Fatty Acids and Derivatives Triacylglycerols Wax Esters Phospholipids Sphingolipids Isoprenoids Lipoproteins Membranes Membrane Structure Membrane Function,11-2,Lipids,General Types Open chain: long nonpolar tail with a polar head saponifiable Fused ring based
2、on the steroid ring skeleton,11-3,Lipid Classes,Fatty acids and their derivatives Triacylglycerols Wax esters Phospholipids phosphoglycerides and sphingomyelin Sphingolipids (not sphingomyelin) Isoprenoids (based on isoprene structure),11-4,Fatty Acids,Lauric acid: a typical saturated fatty acid wit
3、h 12 carbons in the chain (in salt form) Fatty acid: 12-20 carbons, even # carbons, no branching, nonpolar carbon chain, polar COO- group (as anion).,Nonpolar hydrophobic tail,11-5,Fatty Acids-2,An unsaturated fatty acid has one or more carbon-carbon double bonds in the chain. The first double bond
4、is usually at the ninth carbon. The double bonds are not conjugated and are usually cis.,Palmitoleic acid, salt form,Cis double bond results in a bent chain and lower mp.,11-6,Fatty Acids-3,Stearic 18:0 CH3(CH2)16COOH Palmitoleic 16:1D9 CH3(CH2)5CH=CH (CH2)7COOH Linolenic 18:2D9,12 CH3(CH2)4CH=CHCH2
5、CH=CH(CH2)7CO Arachidonic 20:4D5,8,11,14 CH3(CH2)3(CH2CH=CH)4(CH2)3 COOH,11-7,Triacylglycerols,When all three alcohol groups of glycerol form esters with fatty acids a triacylglycerol (triglyceride) is formed.,11-8,Triacylglycerols-2,TAGs which are solids at room temperature are rich in saturated ac
6、ids and are called fats. TAGs which are liquids at room temperature are rich in unsaturated acids and are called oils. e.g. oil seeds include peanut, corn, safflower, palm, and soybean.,11-9,Triacylglycerols-3,Triacylglycerols store fatty acids as fats in animal bodies. Complete oxidation of a fat y
7、ields about 38.9 kJ/g while carbohydrates yield about 17.2 kJ/g. Before a fat can be oxidized, it must be hydrolyzed to the acid anion and glycerol. Biologically this is done by lipases. Chemically base hydrolysis is called saponification.,11-10,Triacylglycerols-4,Saponification (soap making) basic
8、hydrolysis of fats,11-11,Wax Esters,Waxes are typically esters of fatty acids and fatty alcohols. They protect the skin of plants and fur of animal etc. Examples of waxes include carnuba, from the leaves of the Brasilian wax palm, and beeswax.,11-12,Phospholipids,Have hydrophobic and hydrophilic dom
9、ains. Structural components of membranes Emulsifying agents Suspended in water they spontaneously rearrange into ordered structures Hydrophobic group to center Hydrophilic group to water (Next slide) (Basis of membrane structure),11-13,Phospholipids-2,11-14,Phosphoglycerides,When the third OH of gly
10、cerol is esterified to a phosphoric acid or a phosphoric acid ester instead of a carboxylic acid, a phosphoacylglycerol results.,Phosphatidic acid,Phosphatidic ester,11-15,Phosphatidyl esters, egs.,11-16,Sphingolipids,These lipids are based on sphingosine, are found in plants and animals, and are co
11、mmon in the nervous system.,11-17,Sphingolipids-2,A ceramide N-acylsphingosine,A sphingomyelin,11-18,Glycolipids,Glycolipids have a carbohydrate bound to the alcohol of a lipid via a glycosidic link. Frequently a glucose or galactose is bound to the primary alcohol of a ceramide. The compound is cal
12、led a cerebroside. These compounds are found in the cell membranes of nerve and brain cells. Glycolipids have no phosphate. See the next slide for an example,11-19,Glycolipids-2,A cerebroside,11-20,Glycolipids-3: Gangliosides,Sphingolipids with one or more sialic residues are called gangliosodes. Na
13、mes include M, D, T (# residues) and subscripts for number of sugars attached to the ceramide.,11-21,Gangleoside GM2,11-22,Sphingolipid Storage Diseases,11-23,Isoprenoids,Isoprenoids contain a repeating five-carbon unit know as isoprene. They are synthesized from isopentenyl pyrophosphate. Isoprenoi
14、ds consist of terpenes and steroids.,11-24,Terpenes,Monoterpenes: 2 isoprene units geraniol (in germaniums) Sesquiterpenes: 3 isoprene units farnesene (part of citronells oil) Diterpenes: 4 isoprene units phytol (a plant alcohol) Tetraterpenes: 8 isoprene units cartenoids (orange pigment in plants),
15、11-25,Terpenes-2,Some biomolelcule (mixed terpenoids) have isoprenoid (isoprenyl) components. Examples include vitamin E, ubiquinone, vitamin K, and some cytokinins (plant hormones). Some proteins are prenylated (attached to isopreniod groups).,11-26,Terpenes-3,11-27,Steroids,Steroid lipids are base
16、d on the ring system shown below. The next slide shows some examples of steroid sex hormones and of cholesterol, a lipid very important in human physiology.,11-28,Steroid Examples,11-29,Cardiac Glycosides,Cardiac glycosides increase the force of cardiac muscle contraction.,aglycone part,glycone part
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