CARBOHYDRATES

Introduction

Carbohydrates;

 are the most abundant organic compounds in the plant world.

 act as storehouses of chemical energy (glucose, starch, glycogen)
 are components of supportive structures in plants (cellulose), crustacean shells (chitin),
and connective tissues in animals (acidic polysaccharides)
 are essential components of nucleic acids (D-ribose and 2-deoxy-D-ribose).
 account for approximately three-fourths of the dry weight of plants.
 means “hydrate of carbon”
 Animals (including humans) get their carbohydrates by eating plants, but they do not
store much of what they consume. In fact, less than 1% of the body weight of
animals is made up of carbohydrates.

Molecular Formula

 Carbohydrates derive from the formula Cn(H2O)m

 Two examples of carbohydrates with this general molecular formula that can be written
alternatively:
 Glucose (blood sugar): C6H12O6, which can be written as C6(H2O)6
 Sucrose (table sugar): C12H22O11, which can be written as C12(H2O)11
 Not all carbohydrates, however, have this general formula. Some contain too few
oxygen atoms to fit it; some contain too many oxygen. Some also contain nitrogen.
 At the molecular level, most carbohydrates are polyhydroxyaldehydes,
polyhydroxyketones, or compounds that yield them after hydrolysis.

Saccharides- refer to simpler members of the carbohydrate family because of their sweet
taste (Latin: saccharum, “sugar”).

Classifications of Carbohydrates

A. Monosaccharides
 A carbohydrate that cannot be hydrolysed to a simpler compound
 have the general formula CnH2nOn, with one of the carbons being the carbonyl
group of either an aldehyde or a ketone.
 The most common monosaccharides have three to nine carbon atoms.
 The suffix -ose indicates that a molecule is a carbohydrate
 The prefixes tri-, tetr-, pent-, and so forth indicate the number of carbon atoms in
the chain
 Aldose - A monosaccharide containing an aldehyde group
 Ketose - A monosaccharide containing a ketone group
 There are only two trioses(carbohydrates with 3 carbon atoms)
 aldotriose glyceraldehyde
  ketotriose dihydroxyacetone
 D-Monosaccharide- A monosaccharide that, when written as a Fischer projection, has
the -OH group on its penultimate carbon to the right
 L-Monosaccharide- A monosaccharide that, when written as a Fischer projection, has
the -OH group on its penultimate carbon to the left
 Amino Sugars - A monosaccharide in which an -OH group is replaced by an -NH2 group
- Only three amino sugars are common in nature:
 D-glucosamine
 D-mannosamine
 D-galactosamine

Physical Properties of Monosaccharides

 Monosaccharides are colorless, crystalline solids

 all monosaccharides are very soluble in water because hydrogen bonding is possible
between their polar -OH groups and water
 They are only slightly soluble in ethanol and are insoluble in nonpolar solvents such as
diethyl ether, dichloromethane, and benzene
B. Disaccharides
 A carbohydrate containing two monosaccharide units joined by a glycosidic
bond
 two monosaccharide units are joined by a glycosidic bond between the
anomeric carbon of one unit and an -OH group of the other unit.
a. Sucrose(table sugar)
 most abundant disaccharide in the biological world.
 It is obtained principally from the juice of sugar cane and sugar beets.
 In sucrose, carbon 1 of a-D-glucopyranose bonds to carbon 2 of D-
fructofuranose by an a-1,2-glycosidic bond.
 Because the anomeric carbons of both the glucopyranose and
fructofuranose units are involved in formation of the glycosidic bond,
neither monosaccharide unit is in equilibrium with its open-chain form.
Thus sucrose is a nonreducing sugar.
b. Lactose
 Lactose is the principal sugar present in milk.
 It accounts for 5 to 8% of human milk and 4 to 6% of cow’s milk.
 consists of D-galactopyranose bonded by a b-1,4-glycosidic bond to
carbon 4 of D-glucopyranose.
 Lactose is a reducing sugar, because the cyclic hemiacetal of the D-
glucopyranose unit is in equilibrium with its open-chain form and can
be oxidized to a carboxyl group.

c. Maltose
  Maltose derives its name from its presence in malt, the juice from
sprouted barley and other cereal grains.
 It consists of two units of D-glucopyranose joined by a glycosidic
bond between carbon 1 (the anomeric carbon) of one unit and carbon
4 of the other unit.
 Because the oxygen atom on the anomeric carbon of the first
glucopyranose unit is alpha, the bond joining the two units is an a-1,4-
glycosidic bond.
 Maltose is a reducing sugar; the hemiacetal group on the right unit of
D glucopyranose is in equilibrium with the free aldehyde and can be
oxidized to a carboxylic acid

C. Polysaccharides
 Polysaccharides consist of large numbers of monosaccharide units bonded
together by glycosidic bonds
a. Starch: Amylose and Amylopectin
 Starch is used for energy storage in plants. It is found in all plant seeds
and tubers and is the form in which glucose is stored for later use.
 Although the starch from each plant is unique, most starches contain 20
to 25% amylose and 75 to 80% amylopectin
 Amylose - composed of continuous, unbranched chains of as many as
4000 D-glucose units joined by a-1,4-glycosidic bonds.
 Amylopectin - contains chains of as many as 10,000 D-glucose units
also joined by a-1,4-glycosidic bonds.
 Complete hydrolysis of both amylose and amylopectin yields only
D-glucose
b. Glycogen
 Glycogen acts as the energy-reserve carbohydrate for animals.
 it is a branched polysaccharide containing approximately 106 glucose
units joined by a-1,4- and a-1,6-glycosidic bonds.
 The total amount of glycogen in the body of a well-nourished adult human
is about 350g, divided almost equally between liver and muscle.

c. Cellulose
 Cellulose, the most widely distributed plant skeletal polysaccharide,
constitutes almost half of the cell-wall material of wood. Cotton is almost
pure cellulose.
 Cellulose is a linear polysaccharide of D-glucose units joined by b-1,4-
glycosidic bonds. It has an average molecular weight of 400,000 g/mol,
corresponding to approximately 2200 glucose units per molecule.
 Cellulose molecules act much like stiff rods, a characteristic that enables
them to align themselves side by side into well-organized, water-insoluble
fibers in which the OH groups form numerous intermolecular hydrogen
 bonds. This arrangement of parallel chains in bundles gives cellulose
fibers their high mechanical strength.
 insoluble in water
 Humans and other animals cannot use cellulose as food because our
digestive systems do not contain b-glucosidases( enzymes that catalyze
the hydrolysis of b-glucosidic bonds. Instead, we have only a-
glucosidases; hence, we use the polysaccharides starch and glycogen as
sources of glucose.
 many bacteria and microorganisms do contain b-glucosidases and so
can digest cellulose
Acidic Polysaccharides
 group of polysaccharides that contain carboxyl groups and/or sulfuric ester
groups
 play important roles in the structure and function of connective tissues
 glycosaminoglycans- more common name for acidic polysaccharides
a. Hyaluronic Acid
 the simplest acidic polysaccharide present in connective tissue.
 It has a molecular weight of between 105 and 107 g/mol and contains
from 300 to 100,000 repeating units, depending on the organ in which it
occurs.
 It is most abundant in embryonic tissues and in specialized connective
tissues such as synovial fluid, the lubricant of joints in the body, and the
vitreous of the eye, where it provides a clear, elastic gel that holds the
retina in its proper position.
 Hyaluronic acid is also a common ingredient in lotions, moisturizers, and
cosmetics.
 Hyaluronic acid is composed of D-glucuronic acid joined by a b-1,3-
glycosidic bond to N-acetyl-D-glucosamine, which is in turn linked to D-
glucuronic acid by a b-1,4-glycosidic bond
b. Heparin
 a heterogeneous mixture of variably sulfonated polysaccharide chains,
ranging in molecular weight from 6000 to 30,000 g/mol
 synthesized and stored in mast cells (cells that are part of the immune
system and that occur in several types of tissues) of various tissues—
particularly the liver, lungs, and gut.
 It binds strongly to antithrombin III, a plasma protein involved in
terminating the clotting process.
 The larger the molecule, the greater its anticoagulant activity.
 Because of this anticoagulant activity, it is widely used in medicine

Reference:

Bettelheim, F.A., Brown, W.H., Campbell, M.K., Farrel, S.O. (n.d). Introduction to Organic and
Biochemistry (7th ed.). Brooks/Cole Cengage Learning