Chapter 3 Molecules of Life Albia Dugger • Miami Dade College 3.1 Fear of Frying • Trans fats in hydrogenated vegetable oil raise levels of cholesterol in our blood more than any other fat, and directly alter blood vessel function Trans Fats • Trans fats • Partially hydrogenated vegetable oils formed by a chemical hydrogenation process • Double bond straightens the molecule • Pack tightly; solid at room temperature • Bonds are cis or trans, depending on the way the hydrogens are arranged around them Cis and Trans Fatty Acids A Oleic acid, a cis fatty acid. B Elaidic acid, a trans fatty acid. 3.2 Organic Molecules • All molecules of life are built with carbon atoms • We can use different models to highlight different aspects of the same molecule Carbon – The Stuff of Life • Organic molecules are complex molecules of life, built on a framework of carbon atoms • Carbohydrates • Lipids • Proteins • Nucleic acids Carbon – The Stuff of Life • Carbon atoms can be assembled and remodeled into many organic compounds • Can bond with one, two, three, or four atoms • Can form polar or nonpolar bonds • Can form chains or rings Carbon Rings A Carbon’s versatile bonding behavior allows it to form a variety of structures, including rings. B Carbon rings form the framework of many sugars, starches, and fats, such as those found in doughnuts. Representing Structures of Organic Molecules • Structural model of an organic molecule • Each line is a covalent bond; two lines are double bonds; three lines are triple bonds glucose Representing Structures of Organic Molecules • Carbon ring structures are represented as polygons; carbon atoms are implied glucose glucose Representing Structures of Organic Molecules • Ball-and-stick models show positions of atoms in three dimensions; elements are coded by color glucose Representing Structures of Organic Molecules • Space-filling models show how atoms sharing electrons overlap glucose Hemoglobin Molecule: Space-Filling Model A A space-filling model of hemoglobin. Hemoglobin Molecule: Surface Model B A surface model of the same molecule reveals crevices and folds that are important for its function. Heme groups, in red, are cradled in pockets of the molecule. Hemoglobin Molecule: Ribbon Model C A ribbon model of hemoglobin shows all four heme groups, also in red, held in place by the molecule’s coils. Take-Home Message: How are all molecules of life alike? • The molecules of life (carbohydrates, lipids, proteins, and nucleic acids) are organic, which means they consist mainly of carbon and hydrogen atoms • The structure of an organic molecule starts with its carbon backbone, a chain of carbon atoms that may form a ring • We use different models to represent different characteristics of a molecule’s structure; considering a molecule’s structural features gives us insight into how it functions 3.3 From Structure to Function • The function of organic molecules in biological systems begins with their structure • The building blocks of carbohydrates, lipids, proteins, and nucleic acids bond together in different arrangements to form different kinds of complex molecules • Any process in which a molecule changes is called a reaction Assembling Complex Molecules • Monomers • Molecules used as subunits to build larger molecules (polymers) • Polymers • Larger molecules that are chains of monomers • May be split and used for energy What Cells Do to Organic Compounds • Metabolism • Activities by which cells acquire and use energy to construct, rearrange, and split organic molecules • Allows cells to live, grow, and reproduce • Requires enzymes (proteins that increase the speed of reactions) Metabolism ANIMATED FIGURE: Condensation and hydrolysis To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE What Cells Do to Organic Compounds • Condensation • Covalent bonding of two molecules to form a larger molecule • Water forms as a product • Hydrolysis • The reverse of condensation • Cleavage reactions split larger molecules into smaller ones • Water is split Condensation B Condensation. Cells build a large molecule from smaller ones by this reaction. An enzyme removes a hydroxyl group from one molecule and a hydrogen atom from another. A covalent bond forms between the two molecules, and water also forms. Hydrolysis C Hydrolysis. Cells split a large molecule into smaller ones by this water-requiring reaction. An enzyme attaches a hydroxyl group and a hydrogen atom (both from water) at the cleavage site. Functional Groups • Hydrocarbon • An organic molecule that consists only of hydrogen and carbon atoms • Most biological molecules have at least one functional group • A cluster of atoms that imparts specific chemical properties to a molecule (polarity, acidity) Table 3-1 p41 Table 3-1 p41 Table 3-1 p41 ANIMATION: Functional groups To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE Glucose: Conversion of Straight Chain to Ring Form Take-Home Message: How do organic molecules work in living systems? • All life is based on the same organic compounds: complex carbohydrates, lipids, proteins, and nucleic acids • By processes of metabolism, cells assemble these molecules of life form monomers. They also break apart polymers into component monomers. • Functional groups impart chemical characteristics to organic molecules; such groups contribute to the function of biological molecules • An organic molecule’s structure dictates its function in biological systems 3.4 Carbohydrates • Carbohydrates are the most plentiful biological molecules in the biosphere • Cells use some carbohydrates as structural materials; they use others for fuel, or to store or transport energy Carbohydrates • Carbohydrates • Organic molecules that consist of carbon, hydrogen, and oxygen in a 1:2:1 ratio • Three types of carbohydrates in living systems • Monosaccharides (simple sugars) • Oligosaccharides (short-chain carbohydrates) • Polysaccharides (complex carbohydrates) Simple Sugars • Monosaccharides (one sugar unit) are the simplest carbohydrates • Used as an energy source or structural material • Backbones of 5 or 6 carbons • Very soluble in water • Example: glucose Short-Chain Carbohydrates • Oligosaccharides • Short chains of monosaccharides • Example: sucrose, a disaccharide glucose + fructose sucrose + water Stepped Art Complex Carbohydrates • Polysaccharides • Straight or branched chains of many sugar monomers • The most common polysaccharides are cellulose, starch, and glycogen • All consist of glucose monomers • Each has a different pattern of covalent bonding, and different chemical properties Cellulose • Cellulose • Polysaccharide • Major structural material in plants • Consists of long, straight chains of glucose monomers • Does not dissolve in water; not easily broken down • Dietary fiber or “roughage” in our vegetable foods Cellulose Starch • Starch • Polysaccharide • Energy reservoir in plants • Covalent bonding pattern between monomers makes a chain that coils up into a spiral • Does not dissolve easily in water, but less stable than cellulose • An important component of human food Starch Glycogen • Glycogen • Polysaccharide • Covalent bonding pattern forms highly branched chains of glucose monomers • Energy reservoir in animal cells; stored in muscle and liver cells Glycogen Chitin • Chitin • A nitrogen-containing polysaccharide that strengthens hard parts of animals such as crabs, and cell walls of fungi Take-Home Message: What are carbohydrates? • Simple carbohydrates (sugars), bonded together in different ways, form various types of complex carbohydrates • Cells use carbohydrates for energy or as structural materials ANIMATION: Structure of starch and cellulose 3.5 Greasy, Oily – Must Be Lipids • Lipids function as the body’s major energy reservoir, and as the structural foundation of cell membranes • Lipids • Fatty, oily, or waxy organic compounds that are insoluble in water • Triglycerides, phospholipids, waxes, and steroids are lipids common in biological systems Fatty Acids • Many lipids incorporate fatty acids • Simple organic compounds with a carboxyl group joined to a backbone of 4 to 36 carbon atoms • Saturated fatty acids (animal fats) • Fatty acids with only single covalent bonds • Molecules are packed tightly; solid at room temperature • Unsaturated fatty acids (vegetable oils) • Fatty acids with one or more double bonds • Molecules are kinked; liquid at room temperature Saturated and Unsaturated Fatty Acids Fats • Fats • Lipids with one, two, or three fatty acids “tails” attached to glycerol • Triglycerides • Neutral fats with three fatty acids attached to glycerol • The most abundant energy source in vertebrates • Concentrated in adipose tissues (for insulation and cushioning) Triglycerides ANIMATED FIGURE: Triglyceride formation To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE Phospholipids • Phospholipids • Molecules with a polar head containing a phosphate and two nonpolar fatty acid tails • Heads are hydrophilic, tails are hydrophobic • The most abundant lipid in cell membranes • Form lipid bilayers with hydrophobic tails sandwiched between the hydrophilic heads Phospholipids Phospholipids in a Lipid Bilayer hydrophilic head two hydrophobic tails Phospholipids in a Lipid Bilayer one layer of lipids one layer of lipids Waxes • Waxes • Complex mixtures with long fatty-acid tails bonded to longchain alcohols or carbon rings • Protective, water-repellant covering Steroids • Steroids • Lipids with a rigid backbone of four carbon rings and no fatty-acid tails • Cholesterol • Component of eukaryotic cell membranes • Remodeled into bile salts, vitamin D, and steroid hormones such as the female sex hormone estrogen, and the male sex hormone testosterone Estrogen and Testosterone an estrogen testosterone Effects of Estrogen and Testosterone female wood duck male wood duck Take-Home Message: What are lipids? • Lipids are fatty, waxy, or oily organic compounds. Common types include fats, phospholipids, waxes, and steroids • Triglycerides are lipids that serve as energy reservoirs in vertebrate animals • Phospholipids are the main lipid component of cell membranes • Waxes are lipid components of water-repelling and lubricating secretions • Steroids are lipids that occur in cell membranes; some are remodeled into other molecules 3.6 Proteins – Diversity in Structure and Function • All cellular processes involve proteins, the most diverse biological molecule (structural, nutritious, enzyme, transport, communication, and defense proteins) • Cells build thousands of different proteins by stringing together amino acids in different orders From Structure to Function • Protein • An organic compound composed of one or more chains of amino acids • Amino acid • A small organic compound with an amine group (—NH3+), a carboxyl group (—COO-, the acid), and one or more variable groups (R group) Amino Acid Structure Stepped Art Polypeptides • Protein synthesis involves the formation of amino acid chains called polypeptides • Polypeptide • A chain of amino acids bonded together by peptide bonds in a condensation reaction between the amine group of one amino acid and the carboxyl group of another amino acid Polypeptide Formation methionineserine arginineglutamine serine methionine methionine serine Stepped Art ANIMATED FIGURE: Peptide bond formation To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE Levels of Protein Structure • Primary structure • The unique amino acid sequence of a protein • Secondary structure • The polypeptide chain folds and forms hydrogen bonds between amino acids • Tertiary structure • A secondary structure is compacted into structurally stable units called domains • Forms a functional protein Levels of Protein Structure • Quaternary structure • Some proteins consist of two or more folded polypeptide chains in close association • Example: hemoglobin • Some proteins aggregate by thousands into larger structures, with polypeptide chains organized into strands or sheets • Example: hair lysine glycine A protein’s primary structure consists of a linear sequence of amino acids (a polypeptide chain). Each type of protein has a unique primary structure. 1 arginine glycine 2 Secondary structure arises as a polypeptide chain twists into a coil (helix) or sheet held in place by hydrogen bonds between different parts of the molecule. The same patterns of secondary structure occur in many different proteins. 3 Tertiary structure occurs when a chain’s coils and sheets fold up into a functional domain such as a barrel or pocket. In this example, the coils of a globin chain form a pocket. 4 Some proteins have quaternary structure, in which two or more polypeptide chains associate as one molecule. Hemoglobin, shown here, consists of four globin chains (green and blue). Each globin pocket now holds a heme group (red). 5 Many proteins aggregate by the thousands into much larger structures, such as the keratin filaments that make up hair. Stepped Art Figure 3-16 p47 ANIMATED FIGURE: Secondary and tertiary structure To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE Some Functional Proteins • Some fibrous proteins contribute to the structure and organization of cells and tissues; others help cells, cell parts, and bodies move • Sugars bond to proteins to make glycoproteins that allow a tissue or a body to recognize its own cells • Lipids bond to proteins to make lipoproteins such as HDL and LDL, which transport cholesterol to and from the liver HDL: A Lipoprotein lipid protein an HDL particle Take-Home Message: What are proteins? • Proteins are chains of amino acids. The order of amino acids in a polypeptide chain dictates the type of protein. • Polypeptide chains twist and fold into coils, sheets, and loops, which fold and pack further into functional domains • A protein’s shape is the source of its function 3.7 Why Is Protein Structure So Important? • Proteins function only as long as they maintain their correct three-dimensional shape • Changes in a protein’s shape may have drastic health consequences Denaturation • Heat, changes in pH, salts, and detergents can disrupt the hydrogen bonds that maintain a protein’s shape • When a protein loses its shape and no longer functions, it is denatured • Once a protein’s shape unravels, so does its function Prions • Prion diseases are caused by misfolded proteins • Mad cow disease (bovine spongiform encephalitis) • Creutzfeldt–Jakob disease in humans • Scrapie in sheep • All are infectious diseases characterized by deterioration of mental and physical abilities that eventually causes death Variant Creutzfeldt–Jakob Disease (vCJD) Take-Home Message: Why is protein structure important? • A protein’s function depends on its structure. • Conditions that alter a protein’s structure may also alter its function • Protein shape unravels if hydrogen bonds are disrupted 3.8 Nucleic Acids • Nucleotides are subunits of nucleic acids such as DNA and RNA • Some nucleotides have roles in metabolism Nucleotides • Nucleotide • A small organic molecule consisting of a sugar with a fivecarbon ring, a nitrogen-containing base, and one or more phosphate groups • ATP • A nucleotide with three phosphate groups • Important in phosphate-group (energy) transfer base: adenine (A) 3 phosphate groups sugar: ribose A ATP, a nucleotide monomer of RNA, and also an essential participant in many metabolic reactions. Figure 3-18a p49 ANIMATED FIGURE: DNA close up To play movie you must be in Slide Show Mode PC Users: Please wait for content to load, then click to play Mac Users: CLICK HERE A Chain of Nucleotides B A chain of nucleotides is a nucleic acid. The sugar of one nucleotide is covalently bonded to the phosphate group of the next, forming a sugar– phosphate backbone. Nucleic Acids • Nucleic acids • Polymers of nucleotides in which the sugar of one nucleotide is attached to the phosphate group of the next • RNA and DNA are nucleic acids RNA • RNA (ribonucleic acid) • Contains four kinds of nucleotide monomers, including ATP • Important in protein synthesis DNA • DNA (deoxyribonucleic acid) • Two chains of nucleotides twisted together into a double helix and held by hydrogen bonds • Contains all inherited information necessary to build an organism, coded in the order of nucleotide bases The DNA Molecule • The cell uses the order of nucleotide bases in DNA (the DNA sequence) guide production of RNA and proteins Take-Home Message: What are nucleotides and nucleic acids? • Nucleotides are monomers of the nucleic acids DNA and RNA; some have additional roles • DNA’s nucleotide sequence encodes heritable information • RNA plays several important roles in the process by which a cell uses the instructions written in its DNA to build proteins