Carbohydrates - Chemical Structure
Carbohydrates consist of the elements carbon (C), hydrogen (H) and oxygen (O) with a
ratio of hydrogen twice that of carbon and oxygen. Carbohydrates include sugars,
starches, cellulose and many other compounds found in living organisms. In their basic
form, carbohydrates are simple sugars or monosaccharides. These simple sugars can
combine with each other to form more complex carbohydrates. The combination of two
simple sugars is a disaccharide. Carbohydrates consisting of two to ten simple sugars are
called oligosaccharides, and those with a larger number are called polysaccharides.
Sugars
Sugars are white crystalline carbohydrates that are soluble in water and generally have a
sweet taste.
Monosaccharides are simple sugars
Monosaccharide classifications based on the number of carbons
Number
Category
of Examples
Name
Carbons
4 Tetrose Erythrose, Threose
5 Pentose Arabinose, Ribose, Ribulose, Xylose, Xylulose, Lyxose
Allose, Altrose, Fructose, Galactose, Glucose, Gulose, Idose,
6 Hexose
Mannose, Sorbose, Talose, Tagatose
7 Heptose Sedoheptulose
Disaccharides consist of two simple sugars
Disaccharide descriptions and components
Disaccharide Description Component monosaccharides
sucrose common table sugar glucose 1α→2 fructose
maltose product of starch hydrolysis glucose 1α→4 glucose
trehalose found in fungi glucose 1α→1 glucose
lactose main sugar in milk galactose 1β→4 glucose
melibiose found in legumes galactose 1α→6 glucose
Sucrose, also called saccharose, is ordinary table sugar refined from sugar cane or sugar
beets. It is the main ingredient in turbinado sugar, evaporated or dried cane juice, brown
sugar, and confectioner's sugar. Lactose has a molecular structure consisting of galactose
and glucose. It is of interest because it is associated with lactose intolerance which is the
intestinal distress caused by a deficiency of lactase, an intestinal enzyme needed to
absorb and digest lactose in milk. Undigested lactose ferments in the colon and causes
abdominal pain, bloating, gas, and diarrhea. Yogurt does not cause these problems
because lactose is consumed by the bacteria that transform milk into yogurt.
Maltose consists of two α-D-glucose molecules with the alpha bond at carbon 1 of one
molecule attached to the oxygen at carbon 4 of the second molecule. This is called a
1α→4 glycosidic linkage. Trehalose has two α-D-glucose molecules connected through
carbon number one in a 1α→1 linkage. Cellobiose is a disaccharide consisting of two β-
D-glucose molecules that have a 1β→4 linkage as in cellulose. Cellobiose has no taste,
whereas maltose and trehalose are about one-third as sweet as sucrose.
Polysaccharides are polymers of simple sugars
Many polysaccharides, unlike sugars, are insoluble in water. Dietary fiber includes
polysaccharides and oligosaccharides that are resistant to digestion and absorption in the
human small intestine but which are completely or partially fermented by
microorganisms in the large intestine. The polysaccharides described below play
important roles in nutrition, biology, or food preparation.
Starch
Starch is the major form of stored carbohydrate in plants. Starch is composed of a
mixture of two substances: amylose, an essentially linear polysaccharide, and
amylopectin, a highly branched polysaccharide. Both forms of starch are polymers of α-
D-Glucose. Natural starches contain 10-20% amylose and 80-90% amylopectin. Amylose
forms a colloidal dispersion in hot water (which helps to thicken gravies) whereas
amylopectin is completely insoluble.
Glycogen
Glucose is stored as glycogen in animal tissues by the process of glycogenesis. When
glucose cannot be stored as glycogen or used immediately for energy, it is converted to
fat. Glycogen is a polymer of α-D-Glucose identical to amylopectin, but the branches in
glycogen tend to be shorter (about 13 glucose units) and more frequent. The glucose
chains are organized globularly like branches of a tree originating from a pair of
molecules of glycogenin, a protein with a molecular weight of 38,000 that acts as a
primer at the core of the structure. Glycogen is easily converted back to glucose to
provide energy.
Glycogen
Cellulose
Cellulose is a polymer of β-D-Glucose, which in contrast to starch, is oriented with
-CH2OH groups alternating above and below the plane of the cellulose molecule thus
producing long, unbranched chains. The absence of side chains allows cellulose
molecules to lie close together and form rigid structures. Cellulose is the major structural
material of plants. Wood is largely cellulose, and cotton is almost pure cellulose.
Cellulose can be hydrolyzed to its constituent glucose units by microorganisms that
inhabit the digestive tract of termites and ruminants. Cellulose may be modified in the
laboratory by treating it with nitric acid (HNO3) to replace all the hydroxyl groups with
nitrate groups (-ONO2) to produce cellulose nitrate (nitrocellulose or guncotton) which is
an explosive component of smokeless powder. Partially nitrated cellulose, known as
pyroxylin, is used in the manufacture of collodion, plastics, lacquers, and nail polish.
