2.7

Carbohydrates

Sugars are familiar as compounds that taste sweet. Although not all sugars are sweet-tasting, these small organic molecules are an important source of energy for nearly all organisms. Sugars and their polymers are carbohydrates. This name comes from the ratio of C, H, and O in the compounds, in which for each carbon atom (carbo) there are two hydrogens and one oxygen (corresponding to a molecule of water, a hydrate). We can define a carbohydrate as a molecule that contains carbon, hydrogen, and oxygen in a ratio of 1:2:1.

The simplest sugar molecules are called monosaccharides (mah-noh-sak-uh-ride; mono, “one”; sacchar, “sugar”). Monosaccharides are often referred to by the number of carbon atoms they contain. For example, a sugar with the general molecular formula (CH2O)5 is known as a five-carbon sugar. The more common way to express the molecular formula for this sugar is C5H10O5.

When monosaccharides with five or more carbon atoms are dissolved in water, the sugar molecules may exist in either chain form or ring form. Here are the chain and ring forms of a five-carbon sugar called ribose:

Diagram comparing the chain form and ring form of ribose. : Image comparing the chain form and ring form of the 5-carbon monosaccharide ribose. The chain form is labeled “Ribose: chain form” and shows an open-chain model containing four carbon atoms and a hydroxymethyl compound (CH2OH) containing the fifth carbon atom bonded in a vertical row. Each of the five carbon atoms is labeled with a red number 1 through 5. The three center carbon atoms each have a hydroxyl group (OH) bonded on the right and a hydrogen atom on the left. The top carbon atom is bonded to a hydrogen atom and double-bonded to an oxygen atom. The ring form is labeled “Ribose: ring form” and shows a closed-chain model containing four carbon atoms and an oxygen atom bonded in a pentagonal formation. Three of the carbon atoms are each bonded to an atom of hydrogen and a hydroxyl group. Another carbon atom is bonded to an atom of hydrogen and a hydroxymethyl compound (CH2OH) containing the fifth carbon atom. Each of the five total carbon atoms is labeled with a red number 1 through 5.

The one monosaccharide that is found in almost all cells is glucose (C6H12O6). Glucose has a key role as an energy source within the cell, and nearly all the chemical reactions that produce energy for living organisms involve the manufacture or breakdown of this sugar. Fructose, fruit sugar, has the same molecular formula as glucose (C6H12O6), but the atoms are connected in a different pattern, resulting in very different physical and chemical properties. Fructose is nearly twice as sweet as glucose, and it is widely used as a sweetener in processed foods because corn is a cheap source of the sugar.

Scientists often use a shorthand notation to represent the ring form of carbon-containing molecules: the symbols for the carbon atoms, and most of the hydrogen and oxygen atoms, are left out. Here are the structural formula and shorthand notation for glucose:

Diagram comparing the structural formula and shorthand models of glucose. : Image comparing the structural formula and shorthand models of the monosaccharide glucose. The image on the left shows the ring form of glucose in a blue hexagonal formation. Each of six carbon atoms is labeled with a red number 1 through 6. Five carbons and one oxygen are at the vertices of the hexagon. Four carbons are single-bonded to both a hydrogen atom (H) and a hydroxyl group (OH). The last carbon is single-bonded to a hydroxymethyl compound (CH2OH). The ring is labeled “glucose.” The image on the right shows one oxygen atom at the upper right vertex of the hexagon, the same place it appeared in the previous image. This hexagon is otherwise unlabeled.

Monosaccharides can combine to form larger, more complex molecules. Two covalently joined monosaccharides form a disaccharide (di, “two”). Our familiar table sugar, sucrose, is a disaccharide built by linking a molecule of glucose and a molecule of fructose, with the removal of a water molecule (FIGURE 2.13).

Diagram titled “Simple Carbohydrates: Sugars.” : Diagram showing three stages in the formation of the disaccharide sucrose from the monosaccharides glucose and fructose. The image is divided into three rows. At the top of the image, the first stage shows the ring forms (hexagonal formations) of both monosaccharides, labeled “glucose” on the left and “fructose.” Glucose is a hexagon including four hydrogen atoms (H) connected to hydroxyl groups (OH), an oxygen atom (O), and a hydrogen atom (H) connected to a hydroxymethyl compound (CH2OH). Fructose is a hexagon including two hydrogen atoms (H) connected to hydroxyl groups (OH), an oxygen atom (O), a hydroxymethyl compound (CH2OH) connected to a hydrogen atom (H), and a hydroxymethyl compound (CH2OH) connected to a hydroxyl group (OH). All connections are single lines. To symbolize where the covalent bond will take place, a hydroxide compound on the glucose model and the hydrogen portion of a hydroxide compound on the fructose model are highlighted in red, and a plus sign is shown between the two rings. A text box reads, “Two monosaccharides are joined by a covalent bond to form a disaccharide.”  In the middle row of the image, the second stage shows an arrow pointing down to symbolize dehydration and an arrow pointing up to symbolize hydrolysis. Text boxes explain that dehydration reactions link monomers with the release of a water molecule while hydraulic reactions break covalent bonds with the addition of a water molecule. Water (H2O) is shown leaving the dehydration arrow and joining the hydrolysis arrow to symbolize the processes.  The final stage shows the two ring forms of the monosaccharides joined by an oxygen atom highlighted in red to create sucrose, which is also represented by an illustration of a bag of table sugar. The OH from the glucose and the H from the fructose, both highlighted in red in the top image, are not present in the sucrose.

FIGURE 2.13 Monosaccharides Can Bond Together to Form Disaccharides

Glucose and fructose are sugar monomers that, when linked by a covalent bond, form the disaccharide sucrose, or table sugar.

The chemical reaction in which a water molecule is removed as a covalent bond forms is known as a dehydration reaction. The reverse reaction, in which a water molecule is added to break a covalent bond, is called a hydrolytic reaction. Sucrose is broken down in our digestive system through hydrolytic reactions, and the released monomers are absorbed by the intestinal wall and eventually delivered to the bloodstream.

Polysaccharides are large polymers built by linking many monosaccharides. Polysaccharides perform a variety of functions in living organisms (FIGURE 2.14). Cellulose, for example, is a polysaccharide that is bundled into strong parallel fibers that help support the plant body (FIGURE 2.14a). Cotton fabric, made from special cells on the surface of cotton seeds, is mostly cellulose. Carbohydrates are polysaccharides that provide metabolic energy, as we have already seen in the case of glucose. Starch—abundant in a dish of mashed potatoes or steamed rice—is a polysaccharide that serves as an energy storage molecule inside plant cells (FIGURE 2.14b).

Infographic titled “Complex Carbohydrates: Polysaccharides.” : Image showing three common polysaccharides formed from glucose. At the top left, a photo shows a woman slicing vegetables in a kitchen. A callout extends from the woman’s arm to a description of glycogen. A text box explains that glycogen is the main storage polysaccharide in animals and fungi, and is similar to starch but more highly branched than most forms of starch. A microscopic photograph of glycogen, a small black dot, is enlarged. An illustrated diagram of glycogen shows two parallel chains of the polymer, consisting of several glucose molecules in shorthand form (blue hexagons with one oxygen atom labeled), each connected to the next by one oxygen atom highlighted in red.  In the middle of the image, a callout extends from the potatoes in the photo to a description of starch. A text box explains that starch is the main storage polysaccharide in plants and green algae, and that starch-rich foods like potatoes are also good sources of energy for humans. A microscopic photograph of starch grain, an oblong red disk, is enlarged. An illustrated diagram of starch shows one chain of the polymer, consisting of several glucose molecules in shorthand form, each connected to the next by one oxygen atom highlighted in red.  At the bottom left of the image, a callout extends from some herbs shown in the photo to a description of cellulose. A text box explains that cellulose cannot be broken down by the human digestive system, but it does add insoluble fiber to the diet, which is good for intestinal health. A microscopic photograph of cellulose fibers is enlarged. An illustrated diagram of cellulose shows three parallel chains of the polymer, consisting of several glucose molecules in shorthand form, each connected to the next by one oxygen atom highlighted in red. Each chain ends with a hydroxyl group (OH).

FIGURE 2.14 Monosaccharides Can Bond Together to Form Polysaccharides

Cellulose, starch, and glycogen are all polymers built from glucose subunits.

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images Helpful to Know

Humans have only ~200–500 grams of glycogen, stored mainly in the liver and muscles. That’s worth 800–2,000 Calories of stored energy. About 14 hours without food, or a couple of hours of intense exercise, will use up most of the glycogen stored in a typical adult. The fatigue that results is called “hitting the wall” in the world of long-distance runners and bikers. When glycogen runs low, the body switches to “burning” stored lipids, but energy from lipid reserves is released more slowly than from glycogen reserves.

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Cellulose and starch are both built from glucose, but they differ in how the monosaccharides are linked. Starch is water-soluble and easily broken down in our digestive system. Cellulose, on the other hand, is not water-soluble, which is fortunate for owners of 100 percent cotton clothes, who would literally lose their shirts in the wash otherwise. Unlike starch, cellulose cannot be broken down in the human digestive system, and only some bacteria and fungi can use it for energy.

Glycogen is the main storage polysaccharide in animal cells (FIGURE 2.14c), although, as we will see later, most of the surplus energy ingested by animals is stockpiled in the form of storage lipids (“fat”) rather than carbohydrate. The majority of the glycogen reserve in our bodies is stored inside liver cells and skeletal muscle cells.

Concept Check

1. Which atoms are found in all carbohydrates?

Answer Show

Hydrogen, oxygen, and carbon.

2. Which of the following is a polysaccharide and a key structural component of plant cell walls: glucose, sucrose, monosaccharide, cellulose, or glycogen?

Answer Show

Cellulose.