Lipids p Duanqing Pei, Ph. D 裴端卿 Tsinghua University Cell phone:136-8301-7108 peixx003(aum. edu fuxinmiao00@mails.tsinghua.edu.cn
Lipids Duanqing Pei, Ph.D. 裴 端 卿 Tsinghua University Cell phone: 136-8301-7108 peixx003@umn.edu fuxinmiao00@mails.tsinghua.edu.cn
Introduction a diverse group of water-insoluble (hydrophobic) compounds three types of lipids--storage or structural lipids, bioactive lipids
Introduction • A diverse group of water-insoluble (hydrophobic) compounds • three types of lipids—storage or structural lipids, “bioactive” lipids
Lipid basics: Fatty acids Fats and oils--made of fatty acids Fatty acids--long chain hydrocarbon derivatives. Low oxidative state. excellent source of energy
Lipid basics: Fatty acids • Fats and oils—made of fatty acids • Fatty acids—long chain hydrocarbon derivatives. Low oxidative state, excellent source of energy
Fatty acids Carboxylic acids with hydrocarbon chains of 4 to 36 carbons long( C4 to C36) Both saturated and unsaturated(double bonded) Unbranched, branched(methyl group), or three carbon rings
Fatty acids • Carboxylic acids with hydrocarbon chains of 4 to 36 carbons long (C4 to C36) • Both saturated and unsaturated (double bonded) • Unbranched, branched (methyl group), or three carbon rings
Naming Convention ·12:0 6:1(49) 20:4(△5,1.14
Naming Convention • 12:0 • 16:1(D9 ) • 20:4(D5, 8,11, 14)
Some Naturally Occurring Fatty Acids s on name Structure Systematic CH3(CH2)IoCOOH n-Dodecanoi 上 Benzene 2,600 14:0 CH3(CH2)12CO0H n-Tetradecanoic acid Myristic acid 5390.024874 (Latin Myristica meg ge 16:0 CH:(CH2)14CO0H n-Hexadecanoic acid ic acid 63.10.0083348 CH2(H2)1600H n-Octadecanoic acid 6960.0034124 00 CHa(CH2)1BCOOH n-Eicosanoic acid Arachidic acid 76.5 (Latin Arachis legume genus 24:0 CH3(CH2)22CO n- Tetracosanoic acid Lignoceric acid 860 (Latin I wood”+cera,"wax") 16:1(△°) CH3(CH2)s CH-CH(CH2)7C00H cis-9-Hexadecenoic acid Palmitoleic acid 18:1(△°) CH3 (CH2)CH=CH(CH2)7C00H cis-9-Octadecenoic acid ( Lat 13.4 n oleum 18: 2(4.2) CH3(CH2)4CH=CHCH2 CH=- cis, cis-9, 12-0ctadecadienoic Linoleic acid -5 CH(CH2)CO0H ( Greek /inon,“fax") 18:3(49.12.)CH3CH2CH-CHCH2CH- a-Linolenic acid -11 CHCH2CH-CH(CH2)7CO0H Octadecatrienoic acid 20: 4(45.8,1,4) CHa(CH,)4CH=CHCH,CH cis, cis, cis, cis-5, 8, 11, 14- Arachidonic acid 49.5 CHCH.C Icosatetraenoic acid CH(CH2)3( All acids are shown ir nonionized form. At pH 7, all free fatty acids have an ionized carboxylate. Note that numbering of carbon atoms begins at the i carbon TThe prefix n- indicate normalunbranched structure For instance, "dodecanoic" simply indicates 12 carbon atoms, which could be arranged in a varie configuration of each bond is indicated; in biological fatty acids the configuration is almost always cis
Carboxyl oO group Carbon #1 Two representation of the fully saturated acid stearic acid-18: 0 The zigzag form and space-filling model H ydrocarbon chain Carbon #18 a
Two representation of the fully saturated acid, stearic acid—18:0 The zigzag form and space-filling model Carbon #1 Carbon #18
C Unsaturated bond (a cis double bond- rigid bend) Oleic acid(18: 149)(b)
Unsaturated bond (a cis double bondrigid bend) Oleic Acid (18:1D9)
hydro Fully saturated fatty acids in the extended form pack into nearly crystalline arrays, stabilized by many hydrophobic interactions obic Saturated fatty acids (c)
Fully saturated fatty acids in the extended form pack into nearly crystalline arrays, stabilized by many hydrophobic interactions hydrophobic
hydro ess stable obic aggregates Mixture of saturated and unsaturated fatty acids (d)
hydrophobic Less stable aggregates
