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Biomolecules

Organisms contain a wide variety of organic molecules with numerous functions which depend on the chemical structures and properties of these molecules. All organic molecules contain a carbon backbone and hydrogen atoms. The carbon atom is central in the formation of a vast variety of organic molecules ranging in size, shape and complexity; inorganic molecules on the other hand, generally have simpler structures. The outermost shell of a free carbon atom can accommodate eight electrons but is occupied by only four electrons, therefore it can form four covalent bonds and bond with up to four atoms. Alternatively, it can also bond with fewer atoms by forming double or triple bonds. This versatility of carbon atoms allows organic molecules to display intricate structures, such as chains, branches, and rings, among others.

Organic molecules that naturally occur in organisms are called biomolecules. Besides carbon and hydrogen, biomolecules also contain other elements such as oxygen, nitrogen, phosphorus, and sulfur. In general, smaller units of biomolecules come together, as repetitive sequences, to form larger biomolecules. These small modular units of biomolecules are called monomers. Two monomers typically join each other to form a dimer through a process known as dehydration synthesis, which is simply the removal of a hydrogen atom from one monomer and a hydroxyl (OH-) ion from the other monomer to create a water molecule to be expelled out while linking the two monomers with a covalent bond. The reverse of this process is called hydrolysis, in which the molecule splits back into its original monomers with a water molecule providing a hydrogen atom to one monomer and a hydroxyl ion to the other. Many monomers can be attached together by dehydration to form polymers. Sometimes different polymers can come together to form even larger and more complex molecules, which are known as biological macromolecules.

Biomolecules are classified based on the elements that compose them, and their structure and function inside living organisms. Almost all biomolecules can be classified into one of the four general categories: carbohydrates, lipids, proteins, and nucleic acids.

Carbohydrates

Carbohydrate simply means “carbon water” because these molecules are composed of carbon, hydrogen, and oxygen atoms roughly in the ratio of 1:2:1. Carbohydrate monomers are known as monosaccharides, which are also referred to as simple sugars. Glucose (C6H12O6) is the most common monosaccharide in living organisms and is a subunit of many polysaccharides. Numerous organisms also synthesize other six-carbon monosaccharides with the same chemical formula as glucose but slightly different structures, such as fructose and galactose. When two monosaccharides are linked together, they form disaccharides. For example, sucrose is composed of glucose and fructose, whereas lactose contains glucose and galactose. These monosaccharides and disaccharides are used for short-term energy storage in living organisms. Maltose is another disaccharide that is made up of two glucose molecules and is usually formed when polysaccharide chains such as starch and glycogen are broken down during digestion. Starch is a polysaccharide that serves as an energy storage molecule in plants and is made up of two types of glucose polymers: amylose and amylopectin. Amylose constitutes 10-20% of starch and is a helical polymer of glucose. Amylopectin makes up the bulk of the starch and is a branched polymer of glucose. Glycogen is virtually the same as starch, however it is synthesized, stored and used in animal liver and muscle tissues.

Besides serving as energy stores, carbohydrates also have other functions in organisms. The five-carbon monosaccharides, ribose and deoxyribose, are integrated into the nucleic acid structure and are present in every living cell. Moreover, the polysaccharide cellulose, which is a long polymer made up of glucose, serves as a rigid structural material in plants. Humans do not have digestive enzymes to break down cellulose in food, which is also called dietary fiber. However, dietary fiber consumption helps to maintain a healthy gut flora, which in turn contributes to the health of digestive and immune systems1. Similar to plants, some animals and fungi use another polysaccharide, chitin, as a structural molecule. Arthropods use chitin to build and maintain their exoskeletons, whereas fungi incorporate it into their cell walls to maintain rigidity.

Lipids

The second class of biological macromolecules are lipids, which include fats, oils, and waxes. Lipids are hydrophobic molecules that are almost entirely made up of carbon and hydrogen atoms. Often, lipids are grouped in three major categories; triglycerides, phospholipids, and steroids.

The most common type of lipid is triglycerides, which include fats from animals and oils from plants. Triglycerides generally serve as long-term energy storage molecules, except indigestible waxes, which are instead used as a waterproofing substance in both plants and animals. Triglycerides contain three fatty acid chains, which can be either saturated or unsaturated, connected to a glycerol molecule. Saturated fatty acid chains are linear molecules with a maximum number of hydrogen atoms, where every carbon in the chain is connected via a single bond. On the other hand, unsaturated fatty acid chains have kinks due to the presence of at least one double bond. Additionally, unsaturated fats can be “trans” fats if the hydrogens around the double bond oppose each other. While trans fats occur naturally, they are generated during industrial production of saturated vegetable oils with hydrogen. Similar to saturated fatty acids, trans fats stack very well due to their relative linearity. However, trans fats cause problems for human heart health, such as the damaging the lining of arteries and causing inflammation when digested2.

Phospholipids are similar to triglycerides, however, one of the fatty acid chains is replaced with a phosphate-containing polar group. Therefore, phospholipids have a hydrophilic head and two hydrophobic fatty acid tails. These properties of phospholipids are crucial to the cell membrane structure and function.

Steroids are lipids that are composed of fused carbon rings with varying functional groups. Cholesterol is a steroid that is also a cell membrane component. Moreover, cholesterol is used to synthesize other steroids, including sex hormones such as estrogen and testosterone. Although cholesterol is essential for cell membrane structure and hormone synthesis, high levels of plasma cholesterol are implicated in plaque accumulation inside blood vessels and causing coronary disease3.

Proteins

The third class of biological macromolecules are proteins, which are made up of chains of amino acids. There are 20 different amino acids, all with a similar base structure but each has a unique side chain called an ‘R-group’. A single amino acid has an N-terminal end which is an amino group (NH3+) and a C-terminal end which is a carboxyl group (-COOH). These groups link together, N-terminal to C-terminal, in a chain connected by peptide bonds. Proteins are important for maintaining body functions as enzymes, hormones, structural components and transport molecules, and play vital roles in muscle contractibility, immunity and blood clotting. However, issues can arise in protein structure and function, and these issues are often genetic. For instance, normal red blood cells are round, but in people affected by sickle cell anemia, cells have a curved shape with an exposed hydrophobic region, caused by a mutation in a protein called hemoglobin S. This shape reduces the capacity to carry oxygen and causes the cells to get stuck in blood vessels. This results in many detrimental symptoms to the person carrying the mutation, and people who inherit two copies of the sickle cell gene often suffer ill effects or even possibly die because of the reduced capacity of sickled cells to transport oxygen. In a twist, those carrying only one copy of the gene are resistant to infection from malaria, so the disease has been able to be passed on and persists in countries with elevated levels of malaria infections4.

Nucleic Acids

The fourth class of biological macromolecules are the nucleic acids, which are composed of monomers known as nucleotides. These monomers are composed of three parts: a phosphate group, a ribose sugar and a nitrogen base. Nucleotides differ from each other by their nitrogen bases and the type of ribose they contain. Single nucleotides generally act as energy carriers inside cells, as well as function as messenger molecules. However, the nucleotide polymers or nucleic acids such as deoxyribonucleic acid (DNA) or ribonucleic acid (RNA) are hereditary molecules that contain the genetic information to construct cellular products.

Macromolecule Detection

Biological macromolecules in food or other substances can be detected by using their specific chemical properties. For example, monosaccharides have free aldehyde (-CHO) or ketone (-C=O) groups that can reduce other compounds, meaning they are substances that cause other molecules to lose electrons, thus monosaccharides are also known as reducing sugars. This property is used to detect the presence of monosaccharides with an indicator called Benedict’s reagent. This indicator contains copper ions (Cu2+) which are reduced by monosaccharides as observed with a change of the solution color from blue to a reddish orange, though the intensity of the color varies based on the original concentration of the reducing sugar. As such, observation of a green color means that there is only a small amount of reducing sugars present in the solution. Amylose in starch exists in a coiled structure because of the bond angles in the polymer chain. The iodine indicator, iodine-potassium iodide (IKI), reacts with these coiled molecules and will turn the solution a dark bluish-black to indicate the presence of amylose. However, if starch amylose isn’t present, the reaction will not take place, and the solution will remain a yellowish-brown color. A Sudan IV test is performed to test for the presence of lipids. This dye is lipophilic and solubilizes when lipids are present, thus a red color is retained in the presence of lipids. Biuret’s reagent, an indicator for the presence of proteins, contains copper ions (Cu2+) which react with the peptide bonds and turn the solution from blue to dark violet color. This reagent needs to react with a sufficient number of these peptide bonds to produce the expected violet color, so a pinkish color will result if the amino acid chains are not long enough.

References

  1. Rasnik K. Singh, Hsin-Wen Chang, Di Yan, Kristina M. Lee, Derya Ucmak, Kirsten Wong, Michael Abrouk, Benjamin Farahnik, Mio Nakamura, Tian Hao Zhu, Tina Bhutani, Wilson Liao. Influence of diet on the gut microbiome and implications for human health. J Transl Med. 2017, Vol. 15, 73 doi: 10.1186/s12967-017-1175-y.
  2. Siri-Tarino PW, Sun Q, Hu FB, Krauss RM. Meta-analysis of prospective cohort studies evaluating the association of saturated fat with cardiovascular disease. Am J Clin Nutr. 2010, Vol. 91, 3 (535-46).
  3. Joseph L. Goldstein, Michael S. Brown. A Century of Cholesterol and Coronaries: From Plaques to Genes to Statins. Cell. 2015, Vol. 161, 1 (161-72).
  4. Michael Aidoo, Dianne J Terlouw, Margarette S Kolczak, Peter D McElroy, Feiko O ter Kuile, Simon Kariuki, Bernard L Nahlen, Altaf A Lal, Venkatachalam Udhayakumar. Protective effects of the sickle cell gene against malaria morbidity and mortality. Lancet. 2002, Vol. 359, 9314 (1311-1312).

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