Carbohydrates

Introduction
Are carbohydrates good for you? People who wish to lose weight are often told that
carbohydrates are bad for them and should be avoided. Some diets completely forbid
carbohydrate consumption, claiming that a low-carbohydrate diet helps people to lose
weight faster. However, carbohydrates have been an important part of the human diet
for thousands of years; artifacts from ancient civilizations show the presence of wheat,
rice, and corn in our ancestors’ storage areas.

Carbohydrates should be supplemented with proteins, vitamins, and fats to be parts of

a well-balanced diet. Calorie-wise, a gram of carbohydrate provides 4.3 Kcal. For
comparison, fats provide 9 Kcal/g, a less desirable ratio. Carbohydrates contain
soluble and insoluble elements; the insoluble part is known as fiber, which is mostly
cellulose. Fiber has many uses; it promotes regular bowel movement by adding bulk,
and it regulates the rate of consumption of blood glucose. Fiber also helps to remove
excess cholesterol from the body. In addition, a meal containing whole grains and
vegetables gives a feeling of fullness. As an immediate source of energy, glucose is
broken down during the process of cellular respiration, which produces ATP, the energy
currency of the cell. Without the consumption of carbohydrates, the availability of
“instant energy” would be reduced.

Eliminating carbohydrates from the diet is not the best way to lose weight. A low-calorie
diet that is rich in whole grains, fruits, vegetables, and lean meat, together with plenty
of exercise and plenty of water, is the more sensible way to lose weight.
Structure and Function of Carbohydrates

Carbohydrates can be represented by the stoichiometric formula (CH2O)n, where n is

the number of carbons in the molecule. In other words, the ratio of carbon to hydrogen
to oxygen is 1:2:1 in carbohydrate molecules. This formula also explains the origin of
the term “carbohydrate”: the components are carbon (“carbo”) and the components of
water (hence, “hydrate”). Carbohydrates are classified into three subtypes:
monosaccharides, disaccharides, and polysaccharides.

Monosaccharides

Monosaccharides (mono– = “one”; sacchar– = “sweet”) are simple sugars, the most
common of which is glucose. In monosaccharides, the number of carbons usually
ranges from three to seven. Most monosaccharide names end with the suffix –ose. If
the sugar has an aldehyde group (the functional group with the structure R-CHO), it is
known as an aldose, and if it has a ketone group (the functional group with the structure
RC(=O)R′), it is known as a ketose. Depending on the number of carbons in the sugar,
they also may be known as trioses (three carbons), pentoses (five carbons), and or
hexoses (six carbons). See Figure 1 for an illustration of the monosaccharides.
Figure 1. Monosaccharides are classified based on the position of their carbonyl group and the number
of carbons in the backbone. Aldoses have a carbonyl group (indicated in green) at the end of the carbon
chain, and ketoses have a carbonyl group in the middle of the carbon chain. Trioses, pentoses, and
hexoses have three, five, and six carbon backbones, respectively.
The chemical formula for glucose is C6H12O6. In humans, glucose is an important
source of energy. During cellular respiration, energy is released from glucose, and that
energy is used to help make adenosine triphosphate (ATP). Plants synthesize glucose
using carbon dioxide and water, and glucose in turn is used for energy requirements
for the plant. Excess glucose is often stored as starch that is catabolized (the
breakdown of larger molecules by cells) by humans and other animals that feed on
plants.

Galactose and fructose are other common monosaccharides — galactose is found in

milk sugars and fructose is found in fruit sugars. Although glucose, galactose, and
fructose all have the same chemical formula (C6H12O6), they differ structurally and
chemically (and are known as isomers) because of the different arrangement of
functional groups around the asymmetric carbon; all of these monosaccharides have
more than one asymmetric carbon (Figure 2).
PRACTICE QUESTION

Figure 2. Glucose, galactose, and fructose are all hexoses. They are structural isomers, meaning they have the
same chemical formula (C6H12O6) but a different arrangement of atoms.

Monosaccharides can exist as a linear chain or as ring-shaped molecules; in aqueous

solutions they are usually found in ring forms (Figure 3). Glucose in a ring form can
have two different arrangements of the hydroxyl group (−OH) around the anomeric
carbon (carbon 1 that becomes asymmetric in the process of ring formation). If the
hydroxyl group is below carbon number 1 in the sugar, it is said to be in the alpha (α)
position, and if it is above the plane, it is said to be in the beta (β) position.
Figure 3. Five and six carbon monosaccharides exist in equilibrium between linear and ring forms. When the
ring forms, the side chain it closes on is locked into an α or β position. Fructose and ribose also form rings,
although they form five-membered rings as opposed to the six-membered ring of glucose.
Disaccharides
Disaccharides (di– = “two”) form when two monosaccharides undergo a dehydration reaction (also known
as a condensation reaction or dehydration synthesis). During this process, the hydroxyl group of one
monosaccharide combines with the hydrogen of another monosaccharide, releasing a molecule of water
and forming a covalent bond. A covalent bond formed between a carbohydrate molecule and another
molecule (in this case, between two monosaccharides) is known as a glycosidic bond (Figure 4).
Glycosidic bonds (also called glycosidic linkages) can be of the alpha or the beta type. An alpha bond is
formed when the OH group on the carbon-1 of the first glucose is below the ring plane, and a beta bond
is formed when the OH group on the carbon-1 is above the ring plane.

Figure 4. Sucrose is formed when a monomer of glucose and a monomer of fructose are joined in a dehydration reaction
to form a glycosidic bond. In the process, a water molecule is lost. By convention, the carbon atoms in a monosaccharide
are numbered from the terminal carbon closest to the carbonyl group. In sucrose, a glycosidic linkage is formed between
carbon 1 in glucose and carbon 2 in fructose.

Common disaccharides include lactose, maltose, and sucrose (Figure 5). Lactose is a disaccharide
consisting of the monomers glucose and galactose. It is found naturally in milk. Maltose, or malt sugar, is
a disaccharide formed by a dehydration reaction between two glucose molecules. The most common
disaccharide is sucrose, or table sugar, which is composed of the monomers glucose and fructose.

Figure 5. Common disaccharides include maltose (grain sugar), lactose (milk sugar), and sucrose (table sugar).
Polysaccharides
A long chain of monosaccharides linked by glycosidic bonds is known as a polysaccharide (poly–
= “many”). The chain may be branched or unbranched, and it may contain different types of
monosaccharides. The molecular weight may be 100,000 daltons or more depending on the
number of monomers joined. Starch, glycogen, cellulose, and chitin are primary examples of
polysaccharides.

Starch is the stored form of sugars in plants and is made up of a mixture of amylose and
amylopectin (both polymers of glucose). Plants are able to synthesize glucose, and the excess
glucose, beyond the plant’s immediate energy needs, is stored as starch in different plant parts,
including roots and seeds. The starch in the seeds provides food for the embryo as it germinates
and can also act as a source of food for humans and animals. The starch that is consumed by
humans is broken down by enzymes, such as salivary amylases, into smaller molecules, such as
maltose and glucose. The cells can then absorb the glucose.

Starch is made up of glucose monomers that are joined by α 1-4 or α 1-6 glycosidic bonds. The
numbers 1-4 and 1-6 refer to the carbon number of the two residues that have joined to form the
bond. As illustrated in Figure 6, amylose is starch formed by unbranched chains of glucose
monomers (only α 1-4 linkages), whereas amylopectin is a branched polysaccharide (α 1-6
linkages at the branch points).
Figure 6. Amylose and amylopectin are two different forms of starch. Amylose is composed of unbranched chains of glucose
monomers connected by α 1,4 glycosidic linkages. Amylopectin is composed of branched chains of glucose monomers
connected by α 1,4 and α 1,6 glycosidic linkages. Because of the way the subunits are joined, the glucose chains have a
helical structure. Glycogen (not shown) is similar in structure to amylopectin but more highly branched.
Glycogen is the storage form of glucose in humans and other vertebrates and is made up of
monomers of glucose. Glycogen is the animal equivalent of starch and is a highly branched
molecule usually stored in liver and muscle cells. Whenever blood glucose levels decrease,
glycogen is broken down to release glucose in a process known as glycogenolysis.

Cellulose is the most abundant natural biopolymer. The cell wall of plants is mostly made of
cellulose; this provides structural support to the cell. Wood and paper are mostly cellulosic in
nature. Cellulose is made up of glucose monomers that are linked by β 1-4 glycosidic bonds
(Figure 7).

Figure 7. In cellulose, glucose monomers are linked in unbranched chains by β 1-4 glycosidic linkages. Because of the way
the glucose subunits are joined, every glucose monomer is flipped relative to the next one resulting in a linear, fibrous
structure.

As shown in Figure 7, every other glucose monomer in cellulose is flipped over, and the
monomers are packed tightly as extended long chains. This gives cellulose its rigidity and high
tensile strength—which is so important to plant cells. While the β 1-4 linkage cannot be broken
down by human digestive enzymes, herbivores such as cows, koalas, buffalos, and horses are
able, with the help of the specialized flora in their stomach, to digest plant material that is rich in
cellulose and use it as a food source. In these animals, certain species of bacteria and protists
reside in the rumen (part of the digestive system of herbivores) and secrete the enzyme cellulase.
The appendix of grazing animals also contains bacteria that digest cellulose, giving it an important
role in the digestive systems of ruminants. Cellulases can break down cellulose into glucose
monomers that can be used as an energy source by the animal. Termites are also able to break
down cellulose because of the presence of other organisms in their bodies that secrete cellulases.

Figure 8. Insects have a hard outer exoskeleton made of chitin, a type of polysaccharide.

Carbohydrates serve various functions in different animals. Arthropods (insects, crustaceans, and
others) have an outer skeleton, called the exoskeleton, which protects their internal body parts
(as seen in the bee in Figure 8).

This exoskeleton is made of the biological macromolecule chitin, which is a polysaccharide-

containing nitrogen. It is made of repeating units of N-acetyl-β-d-glucosamine, a modified sugar.
Chitin is also a major component of fungal cell walls; fungi are neither animals nor plants and form
a kingdom of their own in the domain Eukarya.