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Fatty Acids: Saturated and Unsaturated: Essential Fatty Acids

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Fatty Acids: Saturated and Unsaturated: Essential Fatty Acids 18UBC3A3 - ALLIED BIOCHEMISTRY I Dr. Narendhirakannan RT Assistant Professor Department of Biochemistry 18UBC3A3 - ALLIED BIOCHEMISTRY I UNIT II (15 Hrs) Lipids: Classification and properties of lipids. Types of fatty acids: saturated and unsaturated: essential fatty acids. Classification and significance of phospholipids: Phosphatidyl choline, phosphatidyl ethanolamine, phosphatidyl serine, phosphatidyl inositol and sphingomyelin. Classification and significance of glycolipids: Cerebrosides and gangliosides. Classification and functions of lipoproteins. Structure and biological functions of cholesterol. UNIT III (15 Hrs) Amino acids: Classification of amino acids (chemical nature). Essential and non-essential amino acids*. Reactions of aminoacids: actions of amino group with benzoic acid, ninhydrin, fluorodinitrobenzene (FDNB) and carbondioxide. Reactions of carboxyl group – decarboxylation and amide formation. Proteins: Definition, classification (chemical nature) and functions of proteins. Structure of proteins-Primary ,secondary, tertiary (myoglobin)and quarternary (hemoglobin). Denaturation and renaturation of proteins. Ampholytes and isoelectric pH. Lipids • The lipids are a large and diverse group of naturally occurring organic compounds that are related by their solubility in nonpolar organic solvents (e.g. ether, chloroform, acetone & benzene) and general insolubility in water. • Lipid, any of a diverse group of organic compounds including fats, oils, hormones, and certain components of membranes that are grouped together because they do not interact appreciably with water. • One type of lipid, the triglycerides, is sequestered as fat in adipose cells, which serve as the energy-storage depot for organisms and also provide thermal insulation. • Some lipids such as steroid hormones serve as chemical messengers between cells, tissues, and organs, and others communicate signals between biochemical systems within a single cell. • The membranes of cells and organelles (structures within cells) are microscopically thin structures formed from two layers of phospholipid molecules. • Membranes function to separate individual cells from their environments and to compartmentalize the cell interior into structures that carry out special functions. • So important is this compartmentalizing function that membranes, and the lipids that form them, must have been essential to the origin of life itself. • Lipids are organic compounds that contain hydrocarbons which are the foundation for the structure and function of living cells. Lipids are nonpolar so they are soluble in nonpolar environments thus not being water soluble because water is polar. Properties of Lipids • Lipids are a heterogeneous group of compounds, including fats, oils, steroids, waxes, and other compounds, which are related more by their physical than by their chemical properties. • Lipids are a class of compounds distinguished by their insolubility in water and solubility in nonpolar solvents. • Lipids are important in biological systems because they form the cell membrane, a mechanical barrier that divides a cell from the external environment. • Lipids also provide energy for life and several essential vitamins are lipids. Lipid Structure • Lipids are the polymers of fatty acids that contain a long, non-polar hydrocarbon chain with a small polar region containing oxygen. Classification of Lipids • Lipids can be classified into two major classes: • Nonsaponifiable lipids, and • Saponifiable lipids. Nonsaponifiable Lipids • A nonsaponifiable lipid cannot be broken up into smaller molecules by hydrolysis, which includes triglycerides, waxes, phospholipids, and sphingolipids. Saponifiable Lipids • A saponifiable lipid contains one or more ester groups allowing it to undergo hydrolysis in the presence of an acid, base, or enzymes. Nonsaponifiable lipids include steroids, prostaglandins, and terpenes. • Each of these categories can be further broken down into non-polar and polar lipids. • Nonpolar lipids, such as triglycerides, are used for energy storage and fuel. • Polar lipids, which can form a barrier with an external water environment, are used in membranes. Polar lipids include glycerophospholipids and sphingolipids. • Fatty acids are important components of all of these lipids. Classification of Lipids • Within these two major classes of lipids, there are several specific types of lipids important to live, including fatty acids, triglycerides, glycerophospholipids, sphingolipids, and steroids. • These are broadly classified as simple lipids and complex lipids. Simple Lipids • Esters of fatty acids with various alcohols. • Fats: Esters of fatty acids with glycerol. Oils are fats in the liquid state. • Waxes: Esters of fatty acids with higher molecular weight monohydric alcohols Complex Lipids • Esters of fatty acids containing groups in addition to alcohol and a fatty acid. • Phospholipids: Lipids containing, in addition to fatty acids and alcohol, a phosphoric acid residue. • They frequently have nitrogen-containing bases and other substituents, eg, in glycerophospholipids the alcohol is glycerol and in sphingophospholipids the alcohol is sphingosine. • Glycolipids (glycosphingolipids): Lipids containing a fatty acid, sphingosine, and carbohydrate. • Other complex lipids: Lipids such as sulfolipids and amino lipids. Lipoproteins may also be placed in this category Precursor and derived lipids • These include fatty acids, glycerol, steroids, other alcohols, fatty aldehydes, and ketone bodies, hydrocarbons, lipid soluble vitamins, and hormones. • Because they are uncharged, acylglycerols (glycerides), cholesterol, and cholesteryl esters are termed neutral lipids. Fatty Acids • Fatty acids are carboxylic acids (or organic acid), often with long aliphatic tails (long chains), either saturated or unsaturated. Saturated fatty acids • When a fatty acid is saturated it is an indication that there are no carbon- carbon double bonds. • The saturated fatty acids have higher melting points than unsaturated acids of the corresponding size due to their ability to pack their molecules together thus leading to a straight rod-like shape. Unsaturated fatty acids • If a fatty acid has more than one double bond then this is an indication that it is an unsaturated fatty acid. • “Most naturally occurring fatty acids contain an even number of carbon atoms and are unbranched.” • Unsaturated fatty acids, on the other hand, have a cis-double bond(s) that create a kink in their structure which doesn’t allow them to group their molecules in straight rod-like shape Essential Fatty Acids • Omega-6 and omega-3 fatty acids are Polyunsaturated fatty acids (PUFA), meaning they contain more than one cis double bond . • In all omega-6 fatty acids, the first double bond is located between the sixth and seventh carbon atom from the methyl end of the fatty acid (n-6). • Similarly, in all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). • One scientific abbreviation for α-linolenic acid (ALA) is 18:3n-3. • Linoleic acid (LA), an omega-6 fatty acid, and α-linolenic acid (ALA), an omega-3 fatty acid, are considered essential fatty acids (EFA) because they cannot be synthesized by humans. • The long-chain omega-3 fatty acids, eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), can be synthesized from ALA, but due to low conversion efficiency, it is recommended to obtain EPA and DHA from additional sources. • LA, arachidonic acid (AA), and DHA are the most common polyunsaturated fatty acids (PUFA) accumulating in tissues. • Both omega-6 and omega-3 fatty acids are important structural components of cell membranes, serve as precursors to bioactive lipid mediators, and provide a source of energy. • Long-chain omega-3 PUFA in particular exert anti-inflammatory effects and it is recommended to increase their presence in the diet. Phospholipids • Phospholipids are a class of lipids that are a major component of all cell membranes. • They can form lipid bilayers because of their amphiphilic characteristic. • The structure of the phospholipid molecule generally consists of two hydrophobic fatty acid "tails" and a hydrophilic "head" consisting of a phosphate group. • The two components are joined together by a glycerol molecule. • The phosphate groups can be modified with simple organic molecules such as choline, ethanolamine or serine. • The first phospholipid identified in 1847 as such in biological tissues was lecithin, or phosphatidylcholine, in the egg yolk of chickens by the French chemist and pharmacist, Theodore Nicolas Gobley. • Biological membranes in eukaryotes also contain another class of lipid, sterol, interspersed among the phospholipids and together they provide membrane fluidity and mechanical strength. • Purified phospholipids are produced commercially and have found applications in nanotechnology and materials science Phosphatidylcholine • Phosphatidylcholines (PC) are a class of phospholipids that incorporate choline as a headgroup. • They are a major component of biological membranes and can be easily obtained from a variety of readily available sources, such as egg yolk or soybeans, from which they are mechanically or chemically extracted using hexane. • They are also a member of the lecithin group of yellow-brownish fatty substances occurring in animal and plant tissues. • Dipalmitoyl phosphatidylcholine (a.k.a. lecithin) is a major component of pulmonary surfactant and is often used in the L/S ratio to calculate fetal lung maturity. • While phosphatidylcholines are found in all plant and animal cells, they are absent in the membranes of most bacteria, including Escherichia coli. • Purified phosphatidylcholine is produced commercially. • This phospholipid is composed of a choline head group and glycerophosphoric acid, with a variety of fatty acids. .
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