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lipids
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*The lipids are a heterogeneous group of compounds,
including fats, oils, steroids, waxes, and related compounds, which are related more by their physical than by their chemical properties *They have the common property of being (1) relatively insoluble in water . (2) soluble in nonpolar solvents such as ether and chloroform *Lipid is not polymers.
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Lipid Functions • Storage form of energy . • Thermal Insulation .
• Protection for delicate organs . • Key component of cell membranes . • Precursors of steroid hormones as sex hormones .
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Classification of lipids
1. Simple lipids: Esters of fatty acids with various alcohols. a. Fats: Esters of fatty acids with glycerol. Oils are fats in the liquid state. b. Waxes: Esters of fatty acids with higher molecular weight monohydric alcohols. 2. Complex lipids: Esters of fatty acids containing other groups in addition to an alcohol and a fatty acid. a. Phospholipids: Lipids containing, in addition to fatty acids and an alcohol, a phosphoric acid residue. They frequently have nitrogen containing bases and other substituent, eg, in glycerophospholipids the alcohol is glycerol and in sphingophospholipids the alcohol is sphingosine.
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b. Glycolipids (glycosphingolipids): Lipids containing a fatty acid, sphingosine, and carbohydrate.
c. Other complex lipids: Lipids such as sulfolipids and aminolipids. Lipoproteins . 3. Precursor and derived lipids: These include fatty acids, glycerol, steroids, other alcohols, lipid-soluble vitamins, and hormones. * Acylglycerols (glycerides),cholesterol, and cholesteryl esters (because they are uncharged ) are termed neutral lipids.
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* Even chain fatty acids are common, odd chain fatty acids are rare, but 3 ‘C’ & 5 ‘c’ are common.
* Fatty acids with 14 – 20 Carbon are commonly seen in natural lipids. * Saturated Fatty acids do not contain double bond ex. Palmitic acid Unsaturated Fatty acids contain one or more double bonds.The double bond is always in cis configuration One double bond – Mono Unsaturated ex. Oleic acid Two or more double bonds – Poly unsaturated fatty acids ex. Linoleic acid Linolenic acid Arachidonic acid
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ESSENTIAL FATTY ACIDS :
ESSENTIAL FATTY ACIDS : *The fatty acids which are not synthesized in the body and they should be supplied in the diet are known as Essential Fatty Acids *All are PolyUnsaturated Fatty Acids eg. Linoleic acid , Linolenic acid Arachidonic acid .
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Fatty acid composition of three food fats
Fatty acid composition of three food fats. Olive oil, butter, and beef fat consist of mixtures of triacylglycerols, differing in their fatty acid composition The melting points of these fats—and hence their physical state at room temperature (25 C)—are a direct function of their fatty acid composition Olive oil has a high proportion of long-chain (C16 and C18) unsaturated fatty acids, which account for its liquid state at 25 C The higher proportion of long-chain (C16 and C18) saturated fatty acids in butter increases its melting point, so butter is a soft solid at room temperature Beef fat, with an even higher proportion of long-chain saturated fatty acids, is a hard solid
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Triacylglyerol Fats : triglycerides which are solid at room temperature ( most saturated triglycerides, e.g. beef, fat, or lard) Oils : triglycerides which are liquid at room temperature ( most triglycerides with several unsaturation, e.g. corn oil, peanut oil, or fish oils)
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Triacylglycerols - Triacylglycerols are esters of glycerol with fatty acids Fats and oils that are widely distributed in both plants & animals are chemically triacylglycerols a) SIMPLE TRIACYLGLYEROLS - All the three fatty acids are same type b) MIXED TRIACYLGLYCEROLS Contains 2-3 different types of fatty acids , more common .
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Function: storage of energy
Triglycerides Function: storage of energy
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Structure of triglycerides
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WAXES * Biological waxes are esters of long-chain (C14 to C36) saturated or unsaturated fatty acids with long-chain (C16 to C30) alcohols * Their melting points (60 to 100 C) are generally higher than those of triacylglycerols. * Waxes serve a diversity of other functions related to their water-repellent properties and their firm consistency.
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Triacontanoylpalmitate, the major component of beeswax, is an ester of palmitic acid with the alcohol triacontanol. A honeycomb, constructed of beeswax, is firm at 25C and completely impervious to water
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* In plankton, the free-floating microorganisms at the bottom of the food chain for marine animals waxes are the chief storage form of metabolic fuel. * Certain skin glands of vertebrates secrete waxes to protect hair and skin and keep it pliable, lubricated and waterproof * Birds, particularly waterfowl, secrete waxes from their preen glands to keep their feathers water-repellent * The shiny leaves of many tropical plants are coated with a thick layer of waxes, which prevent excessive evaporation of water and protects against parasites. * Biological waxes find a variety of applications in the pharmaceutical, cosmetic, and other industries. They are widely used in the manufacture of lotions, ointments, and polishes.
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Phospholipids - Phospholipids are compound lipids containing Glycerol ,Fatty acid ,Phosphate and other groups .Two Classes : Glycerophospholipids In this group alcohol is glycerol Spingophospholipids In this group alcohol is sphingosine . Glycerophospholipids : - Glycerophospholipids Major lipids in Biological membrane Glycerol – 3-phosphate is esterified with 2 Fatty acids usually c1 is esterified with Saturated Fatty acid, and C2 is esterified with unsaturated fatty acid. 1. Phosphatidic acid : 1. Phosphatidic acid is simplest phospholipid .
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THE PRINCIPLE CLASSES OF STORAGE AND MEMBRANE LIPIDS
Point out difference in 3rd position, fatty acid versus phosphate, phosphate versus sugar. All these lipids have either glycerol or sphingosin as the backbone.
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-Sphingomyelin has, in addition to phosphoric
■ The sphingolipids contain sphingosine, a long chain aliphatic amino alcohol, but no glycerol. -Sphingomyelin has, in addition to phosphoric acid and choline, two long hydrocarbon chains, one contributed by a fatty acid and the other by sphingosine.
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■ The polar lipids, with polar heads and nonpolar
tails, are major components of membranes The most abundant are the glycerophospholipids which contain fatty acids esterified to two of the hydroxyl groups of glycerol, and a second alcohol, the head group, esterified to the third hydroxyl of glycerol via a phosphodiester bond. - Other polar lipids are the sterols. ■ Glycerophospholipids differ in the structure of their head group; common glycerophospholipids are phosphatidylethanolamine and phosphatidylcholine. The polar heads of the glycerophospholipids carry electric charges at pH near 7.
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* Glycolipids are composed of amino alcohol sphingosine + long chain fatty acid + monosaccharide unites . * Glycolipids are important constituents of nervous tissue such as brain and the outer leaflet of the cell membrane
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Cell membrane
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Steroids * Steroid nucleus consists of four fused rings . * Sterols have steroid nucleus and a hydroxyl group * Sterols are structural lipids present in the membranes of most eukaryotic cells. * Cholesterol, the major sterol in animal, is both a structural component of membranes and precursor to a wide variety of steroids.
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Cholesterol Steroid nucleus Cholesterol, an amphipathic lipid, is an important component of membranes It is the parent molecule from which all other steroids in the body, including major hormones such as the sex hormones, D vitamins, and bile acids, are synthesized.
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Combination of Biomolecules
Lipoproteins (blood transport molecules) Glycoproteins (membrane structure) Glycolipids (membrane receptors)
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Protein Hybrids Lipoproteins :in membranes and transportation of materials Glycoproteins : antibodies, cell surface proteins Nucleoproteins : ribosomes
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Nucleic Acids DNA & RNA
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• Two types : • - Deoxyribonucleic acid (DNA) • - Ribonucleic acid (RNA) • Made of polymer of nucleotides joined together by phosphodiester bond
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DNA & RNA function DNA carries and transmits the genetic information .
RNA carry the genetic information from nucleus to cytoplasm for protein synthesis . RNAs are involved in most steps of gene expression and protein biosynthesis.
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Base + sugar
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Nucleoside glycosidic bond phosphoester bond
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Nucleotides ■ A nucleotide consists of a nitrogenous base (purine or pyrimidine), a pentose sugar, and one or more phosphate groups. Nucleic acids are polymers of nucleotides, joined together by phosphodiester linkages between the 5’- hydroxyl group of one pentose and the 3’- hydroxyl group of the next. Nucleotides function as energy transfer molecules : ATP , Cyclic AMP , NAD & FAD
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A Nucleotide Adenosine Mono Phosphate (AMP)
OH HO Phosphate NH2 N Base - H+ OH O CH2 Sugar H 2’ 3’ 4’ 5’ 1’ Nucleotide Nucleoside OH
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Purines Pyrimidines Uracil CH3 N O NH Thymine N Adenine NH2 NH2 O N NH
(RNA) CH3 N O NH Thymine (DNA) N Adenine NH2 NH2 O N NH Guanine N O NH2 Cytosine
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Polynucleotide Formation
Dehydration reaction to form phosphodiester bond
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Phosphodiester linkages in the covalent backbone of DNA and RNA
Phosphodiester linkages in the covalent backbone of DNA and RNA The phosphodiester bonds link successive nucleotide units The backbone of alternating pentose and phosphate groups in both types of nucleic acid is highly polar.
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DNA STRUCTURE • The two strands are complementary & anti-parallel
two polynucleotide chains are twisting around each other in the form of a double helix • The two strands are complementary & anti-parallel • Wound around each other in a rightward direction • stabilized by H-bonding between bases in adjacent strands. • The bases are in the interior of the helix • Purine bases form hydrogen bonds with pyrimidine.
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Sugar phosphate backbone of
DNA
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D N A B A S E S SUGAR-PHOSPHATE BACKBONE 5’Phosphate group
3’Hydroxyl group SUGAR-PHOSPHATE BACKBONE H P O HO CH2 OH NH2 N NH B A S E S O H P HO CH2 H2N N HN H OH P O HO CH2 CH3 HN N H2O D N A H P HO O CH2 N H2N H2O 3’Hydroxyl group 5’Phosphate group
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5' C-G-A-T-T-G-C-A-A-C-G-A-T-G-C 3'
| | | | | | | | | | | | | | | 3' G-C-T-A-A-C-G-T-T-G-C-T-A-C-G 5'
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Base Pair Rule • Adenine always base pairs with Thymine (or Uracil if RNA)by two hydrogen bonds . • Cytosine always base pairs with Guanine by Three hydrogen bonds .
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Base Pairing Guanine And Cytosine
H O N Guanine - N O H Cytosine + + - - +
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Base Pairing Adenine And Thymine
- + Adenine CH3 N O H + - Thymine
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Base Pairing Adenine And Cytosine
H Cytosine - + N H - + Adenine
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Base Pairing Guanine And Thymine
CH3 N O H + - Thymine H O N Guanine + -
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RNA Single strand of polynucleotides .
Purine bases are A & G , prymidines are C & U. • In viruses it can carry out DNA role * What are the differences in structure and function between DNA & RNA ?
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