Carbohydrates: Life’s
•Carbohydrates are sugars and provide energy when
consumed.
•Our bodies break down carbohydrates to extract
energy. Carbon dioxide and water are released in the
process.
•Glucose is the primary carbohydrate our bodies use to
produce energy.
•Carbohydrates are classified as biomolecules.
•Simple carbohydrates are referred to as simple sugars
and are often sweet to the taste.
•Consumption of more sugar than is needed for energy
results in conversion of these sugars to fat.
•Complex carbohydrates include starches and the plant
and wood fibers known as cellulose.
•Carbohydrates are found on the surface of cells where
they act as “road signs” allowing molecules to
distinguish one cell from another.
•ABO blood markers found on red blood cells are
made up of carbohydrates. They allow us to
distinguish our body’s blood type from a foreign
blood type.
•Carbohydrates in our body prevent blood clots. They
are also found in our genetic material.
Classes of Carbohydrates
•Monosaccharides are the simplest carbohydrates.
They cannot be broken down to smaller
carbohydrates.
•Disaccharides consist of two monosaccharide units
joined together; they can be split into two
monosaccharides. Sucrose, table sugar, can be broken
down into glucose and fructose.
•Oligosaccharides contain anywhere from three to
nine monosaccharide units. ABO blood groups are
oligosaccharides.
•Polysaccharides are large molecules containing 10 or
more monosaccharide units. Carbohydrate units are
connected in one continuous chain or the chain can be
branched.
•Monosaccharides contain the elements carbon,
hydrogen, and oxygen, and have the general formula
Cn(H2O)n, where n is a whole number 3 or greater.
•Monosaccharides contain several functional groups.
They contain the hydroxyl group represented as –OH.
They also contain a carbonyl group, which is an
oxygen double bonded to a carbon atom. The carbonyl
group may be an aldehyde or a ketone.
The functional groups of glucose are shown in the
figure below.
Functional Groups in Monosaccharides— Alcohols,
Aldehydes, and Ketones Alcohols
•Alcohol is an organic compound containing the –OH
group.
•Ethanol is one of the simplest alcohols and is
prepared from the fermentation of simple sugars in
grains and fruits. Ethanol is present in beer and
liquors, and is used as an alternative fuel blend, such
as gasohol and E85 (85% ethanol and 15% gasoline).
Alcohols
•Alcohols are classified by the number of alkyl groups
attached to the carbon atom containing the hydroxyl
group. The number of alkyl groups impacts the
reactivity of the alcohol.
•Primary (1degree) alcohols have one alkyl group
attached to the alcoholic carbon.
•Secondary (2degree) alcohols have two alkyl groups
attached to the alcoholic carbon.
•Tertiary (3degree) alcohols have three alkyl groups
attached to the alcoholic carbon.
Alcohols
• Monosaccharides contain both primary and
secondary alcohols.
Aldehydes
•An aldehyde is
an organic
compound
containing the carbonyl group.
•Benzaldehyde, a compound responsible for the aroma •For example, glucose, the most abundant
of almonds and cherries, is one example. monosaccharide found is nature, contains six carbons
• Members of this family always contain a carbonyl and an aldehyde group. It is classified as an
group with a hydrogen aldohexose.
atom bonded to one •Fructose, known as fruit sugar, contains six carbons
side and an alkyl or and a ketone group. It is classified as a ketohexose.
aromatic bonded to the Aldohexose and ketopentose differ in the number of
other. An exception is carbon atoms and in the type of carbonyl group they
formaldehyde (a contain.
preservative), which
has two hydrogens
bonded to the carbonyl
group.
Aldehydes
• Monosaccharides
can contain an
aldehyde group on
one end of the
molecule in addition
to multiple hydroxyl
groups.

Ketones
•A ketone also
contains the carbonyl
group, but has an
alkyl or aromatic group on both sides of the carbonyl
group.
•Acetone is the simplest ketone. It is the main
component of fingernail polish
remover.
•A wide variety of biologically
important compounds contain a ketone
group.
•Pyruvate is a ketone-containing compound formed
during the breakdown of glucose.
•Butanedione, the flavor of butter, contains two ketone
groups.
•Monosaccharides that contain an aldehyde group are
referred to as an aldose. Those that contain a ketone
group are referred to as a ketose.
•Monosaccharides are classified according to the
number of carbon atoms. Most common
monosaccharides have three to six carbon atoms.
–Triose contains three carbons.
–Tetrose contains four carbons.
–Pentose contains five carbons.
–Hexose contains six carbons.
•Carbohydrates are further classified on whether they
contain an aldehyde or ketone group.
Stereochemistry in Monosaccharides
Multiple chiral centers
•Recall that a chiral center is a carbon atom that has
four different atoms or groups of atoms attached to it.
•Glucose, a ketohexose, contains four different chiral
centers, each with a tetrahedral geometry.
Multiple chiral centers
• Carbons 2 through 5 of glucose are tetrahedral and
have four different atoms or groups of atoms
attached. Carbons 1 and 6 are not chiral centers.
Why?
Multiple chiral centers
•Groups bonded to each chiral center have two
different arrangements or mirror images, which result
in stereoisomers.
•The number of stereoisomers for a molecule
increases with the number of chiral centers in the
molecule.
•The general formula for determining the number of
stereoisomers is 2n, where n is the number of chiral
centers present in the molecule.
•Glucose has 4 chiral centers, so there are 16
stereoisomers, 24 = 16.
Representing stereoisomers—the Fischer projection
•Fischer projection is a simple way of indicating chiral
molecules by showing their threedimensional structure
in two dimensions, without showing all the wedges
and dashes on all the chiral centers.
•In the Fischer projection, horizontal lines on a chiral
center represent wedges, and vertical lines on a chiral
center represent dashes.
•Representing stereoisomers—the Fischer projection
–In the Fischer projection, a chiral carbon is not
shown, but is implied at the intersection of lines.
–Consider the Fischer projection of glyceraldehyde,
the simplest aldose, shown on the next slide.
Representing stereoisomers—the Fischer projection
Representing stereoisomers—the Fischer projection
•D and L designations of sugars are based on the
Fischer projection positioning in glyceraldehyde.
•All D-sugars have the –OH on the chiral carbon
farthest from the carbonyl group on the right side of
the molecule.
•All L-sugars have the –OH on the chiral carbon
farthest from the carbonyl group on the left side of the
molecule.
•Most sugars in nature have the D designation.
Representing stereoisomers—the Fischer projection
•Enantiomers are written as if there is a mirror placed
between the two molecules.
•Enantiomers of D- and L-glucose are:
Stereoisomers that are not enantiomers
•How are all stereoisomers of D-glucose related since
only one mirror image exists for any stereoisomer?
•Stereoisomers that are not enantiomers are called
diastereomers.
•Diastereomers are stereoisomers that are not exact
mirror images.
Some Important Monosaccharides
•Glucose is the most abundant monosaccharide found
in nature.
•Glucose is also known as dextrose, blood sugar, and
grape sugar.
•Glucose is broken down in cells to produce energy.
•Diabetics have difficulty getting glucose in their
cells, which is why they must monitor their blood
glucose levels regularly.
•Glucose is one of the monosaccharides of sucrose
(table sugar) and lactose (milk sugar) as well as the
polysaccharides glycogen, starch, and cellulose.
•Galactose is found combined with glucose in the
disaccharide lactose, which is present in milk and
other dairy products.
•A single chiral center (carbon 4) in galactose is
arranged opposite that of glucose, which makes it a
diastereomer of glucose.
•Diastereomers that differ by one chiral center are
called epimers.
•Mannose, a monosaccharide, is found in some fruits
and vegetables.
•Cranberries contain high amounts of mannose, which
has been shown to be effective in urinary tract
infections.
•Mannose is an epimer of glucose.
•Fructose, a ketose, is commonly referred to as fruit
sugar or levulose.
•Fructose is combined with glucose to give sucrose, or
table sugar.
•Fructose is the sweetest monosaccharide and is found
in fruits, vegetables, and honey.
•Fructose is not an epimer of glucose, but it can be
broken down for energy in the body.
•Pentoses are five-carbon sugars and include ribose
and 2-deoxyribose, which are parts of nucleic acids
that make up genetic material.
•Ribonucleic acid (RNA) contains ribose, and
deoxyribonucleic acid (DNA) contains 2-
deoxyribose.
•The difference between these two pentoses is the
absence of an oxygen atom on carbon 2 of
deoxyribose.
•Ribose is also found in the vitamin riboflavin and
other biologically important molecules.

Oxidation and Reduction
•Oxidation and reduction reactions are commonly
called redox reactions.
•Oxidation is a loss of electrons.
•Reduction is a gain of electrons.
•The mnemonic “OIL RIG” helps remember redox
reactions. Oxidation Is Loss, Reduction Is Gain.
•When copper metal (shiny orange metal) is exposed
to oxygen, an ionic compound, copper(II) oxide, is
produced. This compound is greenish in color. This
reaction is shown as:
•Aldose sugars are oxidized by Cu2+ ion, while the
Cu2+ ion is reduced to Cu+ ion.
The product of this reaction, copper(I) oxide (Cu2O),
is not soluble and forms a brick red precipitate in
solution.
•Aldoses are easily oxidized. They serve as reducing
agents and are referred to as reducing sugars.
•Fructose and other ketoses are also reducing sugars,
even though they do not contain an aldehyde group.
•The oxidizing agents can cause a rearrangement of
the ketose to an aldose.
This rearrangement can be shown as:

•The copper atoms in the reactant lose electrons to

form the Cu2+ ions in the product. The copper has
undergone oxidation.
•The electrons lost by copper atoms are transferred to
the oxygen atom, which then becomes O2-. Oxygen
has undergone reduction.
•While the copper was being oxidized, oxygen was
being reduced.
•Copper then becomes the reducing agent (causing
oxygen to be reduced) and oxygen is the oxidizing
agent (causing copper to be oxidized).
•Organic molecules are oxidized if they gain oxygen
or lose hydrogen, and they are reduced if they lose
oxygen or gain hydrogen.
•Some biological reactions undergo oxidation and
reduction. A summary of these characteristics are as

•Benedict’s test can be used in urine dipsticks to

follows:
Monosaccharides and Redox
•An aldehyde functional group can undergo oxidation
by gaining oxygen or it can undergo reduction by
gaining hydrogen.
•During oxidation, aldehydes form carboxylic acids,
and during reduction, they form alcohols.
•In monosaccharides, oxidation produces a sugar acid,
and reduction produces a sugar alcohol.
determine the level of glucose in urine. Excess glucose
in urine suggests high levels of glucose in blood,
which is an indicator of diabetes.
•Aldoses or ketoses can be reduced by hydrogen under
the correct conditions, producing sugar alcohols.
•Sugar alcohols are produced commercially as
artificial sweeteners and found in sugar-free foods.
Reduction of glucose produces the sugar alcohol,
sorbitol, which is an artificial sweetener.

•Benedict’s test is a useful test to determine the

presence of an oxidation reaction that occurs with
sugars.
 •In a five-membered and six-membered ring, the
anomers are distinguished similarly.
•In the alpha anomer, the –OH on the anomeric carbon
is trans to the carbon outside the ring.
•In the beta anomer, the –OH on the anomeric carbon
is cis to the carbon outside the ring.

•When glucose levels are high in the blood stream,
sorbitol can be produced by an enzyme called aldose
reductase.
•High levels of sorbitol can contribute to cataracts,
which is a clouding of the lens in the eye.
•Cataracts are commonly seen in diabetics.
Disaccharides
Condensation and Hydrolysis—Forming and Breaking
Glycosidic Bonds
•The –OH group that is most reactive in a
monosaccharide is the one on the anomeric carbon.
•When this hydroxyl group reacts with another
hydroxyl group on another monosaccharide a
glycosidic bond is formed.

Monosaccharide Structure
•Carbonyl groups can also react with a hydroxyl
functional group (–OH).
Formation of glycosides is an example of another type
•When this happens, a hemiacetal functional group is
of organic reaction. During this reaction, a molecule
formed as shown:
of water is eliminated as two molecules join.
•Condensation reaction is a type of reaction that
occurs when two molecules are joined and a water
molecule is produced. This type of reaction is referred
to as a dehydration reaction.
•Hydrolysis reaction is the reverse of a condensation
reaction. A larger molecule forms two smaller
A hemiacetal can form within a monosaccharide since molecules and water is consumed as a reactant.
it contains both a carbonyl and several hydroxyl
functional groups.
•The carbonyl carbon that reacts to form the
hemiacetal is referred to as the anomeric carbon.
•Two ring arrangements can be produced. These are
termed anomers, and are referred to as the alpha ()
and beta (β) anomer. Condensation reactions occur between different types
of functional groups that contain an –H in a polar
•The position of the –OH group on the anomeric
carbon relative to the position of the carbon outside bond, like O–H or N–H, and an –OH group that can be
removed to form water.
the ring determines the type of anomer present.
•In the six-member ring (five carbons and an oxygen) Naming Glycosidic Bonds
•In the slide showing the formation of maltose, we
form of D-isomers, called a pyranose, carbon 6 is
always drawn on the top side of the ring.
•In the  anomer, the –OH on the anomeric carbon is
trans to the carbon outside the ring.
•In the β anomer, the –OH on the anomeric carbon is
cis to the carbon outside the ring.
•D-Fructose contains both a ketone group and several
hydroxyl groups.
•The ring structure of D-fructose contains four
carbons and an oxygen to form a five-membered ring
called a furanose. observed that the glycosidic bond was in the alpha
•In a furanose, carbons 1 and 6 remain outside the position. If that bond had been in the beta position, a
ring.
different molecule would have been formed with a
different three-dimensional structure.
•In naming glycosidic bonds, it is necessary to name
the configuration as well as the carbons involved in
the bond formation.
•In the case of maltose, the glycosidic bond is
specified as α(1→4) and is simply stated as alpha-one-
four.
•If the –OH group had been in the beta configuration
when the glycosidic bond was formed, the bond would
be in the β(1→4) configuration. The molecule formed
would be named cellobiose and would have a different
two-dimensional and three-dimensional shape than
maltose.
Three Important Disaccharides—Maltose, Lactose,
and Sucrose
The formation of these three common disaccharides is
outlined below.
Maltose
•Maltose is known as malt sugar.
•It is formed by the breakdown of starch.
•Malted barley, a key ingredient in beer, contains high
levels of maltose.
•During germination of barley seeds, the starch goes
through hydrolysis to form maltose. This process is
halted by drying and roasting barley seeds prior to
their germination.
•One of the anomeric carbons is free, so maltose is a
reducing sugar.
• The glycosidic bond is α(1→4).
Lactose
•Lactose is known as milk sugar.
•It is found in milk and milk products.
•An intolerance to lactose can occur in people who
inherit or lose the ability to produce the enzyme
lactase that hydrolyzes lactose into its monosaccharide
units.
•The glycosidic bond is (1→4).
•One of the anomeric carbons is free, so lactose is a
reducing sugar.
Sucrose
•Sucrose is known as
table sugar.
•It is the most
abundant disaccharide
found in nature.
•Sucrose is found in
sugar cane and sugar beets.
•The glycosidic bond is  (1→2).
•Both anomeric carbons of the monosaccharides in
sucrose are bonded, therefore, sucrose is not a
reducing sugar. It will not react with Benedict’s
reagent.
Polysaccharides
Polysaccharides are large molecules of
monosaccharides that are connected to each other
through their anomeric carbons. There are two types
of polysaccharides:
1.Storage polysaccharides contain only  -glucose
units. Three important ones are starch, glycogen, and
amylopectin.
2.Structural polysaccharides contain only -glucose
units. Two important ones are cellulose and chitin.
Chitin contains a modified -glucose unit.
Storage and structural polysaccharides are made up of
glucose units, but they are structurally and
functionally different because of their glycosidic
bonds and difference in branching.  
Storage Polysaccharides
Amylose and amylopectin—starch
•Starch is a mixture of amylose and amylopectin and
is found in plant foods.
•Amylose makes up 20% of plant starch and is made
up of 250–4000 D-glucose units bonded α(1→4) in a
continuous chain.
•Long chains of amylose tend to coil.
•Amylopectin makes up 80% of plant starch and is
made up of D-glucose units connected by α(1→4)
glycosidic bonds.
Amylose and amylopectin—starch
•About every 25 glucose units of amylopectin, a
branch of glucose units are connected to the glucose
by an α(1→6) glycosidic bond.
•During fruit ripening, starch undergoes hydrolysis of
the α(1→4) bonds to produce glucose and maltose,
which are sweet.
•When we consume starch, our digestive system
breaks it down into glucose units for use by our
bodies.
Glycogen
•Glycogen is a storage polysaccharide found in
animals.
•Glycogen is stored in the liver and muscles.
•Its structure is identical to amylopectin, except that
α(1→6) branching occurs about every 12glucose
units.
•When glucose is needed, glycogen is hydrolyzed in
the liver to glucose.
Structural Polysaccharides
Cellulose
•Cellulose contains glucose units bonded (1→4).
•This glycosidic bond configuration changes the three-
dimensional shape of cellulose compared with that of
amylose.
•The chain of glucose units is straight. This allows
chains to align next to each other to form a strong
rigid structure.

Cellulose
•Cellulose is an insoluble fiber in our diet because we
lack the enzyme cellulase to hydrolyze the (1→4)
glycosidic bond.
•Whole grains are a good source of cellulose.
•Cellulose is important in our diet because it assists
with digestive movement in the small and large
intestine.
•Some animals and insects can digest cellulose
because they contain bacteria that produce cellulase.
Chitin
•Chitin makes up the exoskeleton of insects and
crustaceans and cell walls of some fungi.
•It is made up of N-acetylglucosamine containing
(1→4) glycosidic bonds.
•It is structurally strong.
•Chitin is used as surgical thread that biodegrades as a
wound heals.
•It serves as a protection from water in insects.
•Chitin is also used to waterproof paper, and in
cosmetics and lotions to retain moisture.
Carbohydrates and Blood
ABO Blood Types
•ABO blood types refer to carbohydrates on red blood
cells.
•These chemical markers are oligosaccharides that
contain either three or four sugar units.
•Sugar units are D-galactose, L-fucose,
N-acetylglucosamine, and N-acetylgalactosamine.
The following shows the carbohydrates and their
attachments in type O, type A, and type B blood. Type
AB blood has both type A and type B sets on their
blood cells.  
•Type O blood is considered the universal donor while
type AB blood is considered the universal acceptor.
•The following table shows the compatibility of blood
groups.
Heparin
•Heparin is a medically important polysaccharide
because it prevents clotting in the bloodstream.
•It is a highly ionic polysaccharide of repeating
disaccharide units of an oxidized monosaccharide and
D-glucosamine. Heparin also contains sulfate groups
that are negatively charged.
•It belongs to a group of polysaccharides called
glycosaminoglycans.

Chapter Summary
Classes of Carbohydrates
Carbohydrates are classified as monosaccharides
(simple sugars), disaccharides (two monosaccharide
units), oligosaccharides (three to nine monosaccharide
units), and polysaccharides (many monosaccharide
units).
Monosaccharides
•A monosaccharide has a molecular formula of
Cn(H2O)n, where n = 3–6.
•Fischer projections that highlight chiral centers are
used to represent monosaccharides.
•Most monosaccharides in nature are D-isomers.
•Multiple chiral centers lead to enantiomers or
diastereomers.
•Important monosaccharides are glucose, galactose,
fructose, mannose, ribose, and deoxyribose.
Oxidation and Reduction Reactions
•Oxidation is a loss of electrons and reduction is a
gain of electrons.
•These are common types of reactions in organic
molecules.
•For organic molecules, oxidation is the addition of
oxygen and reduction is the addition of hydrogen.
•The anomeric carbon of carbohydrates is highly
reactive and can be oxidized to a carboxylic acid or
reduced to an alcohol.
•Monosaccharides are considered reducing sugars
because their anomeric carbon can react.
Ring Formation—The Truth about Monosaccharide
Structure
•A hydroxyl group and the carbonyl group can react to
enclose the hydroxyl’s oxygen in a ring.
•Because the carbonyl group is planar, two possible
ring arrangements about the anomeric carbon occur
when the ring forms. These are termed the α and
anomers.
Disaccharides
•Condensation and hydrolysis are common reactions
that occur in biomolecules.
•Condensation reactions produce a water molecule
while bonding two molecules together.
•Hydrolysis reactions consume a molecule of water
while a molecule is broken into two smaller
molecules.
•Carbohydrates form glycosides when an anomeric
carbon reacts with a hydroxyl group on a second
molecule. The bond formed is called a glycosidic
bond.
•Glycosidic bonds are named by designating the
anomer of the reacting monosaccharide and the
carbons that are bonded, for example, α(1→4).
Polysaccharides
•A polysaccharide consists of many monosaccharide
units bonded together through glycosidic bonds.
•Glucose is stored as glycogen in animals and starch
in plants.
•Starch consists of amylose, a linear chain of glucose,
and amylopectin, a branched chain of glucose.
•Glycogen contains many more branches in its
structure than amylopectin.
•Two important polysaccharides are cellulose in plants
and chitin in arthropods and fungi.
•Cellulose consists of (1→4) and is the structural
component of plants. It has a linear structure.
•Chitin is linear. It contains N-acetylglucosamine.
•Cellulose and chitin form strong, water-resistant
materials when the linear chains are aligned to each
other.
Carbohydrates and Blood
•The ABO blood groups are oligosaccharides on the
surface of red blood cells.
•The O blood group is considered the universal donor.
•Heparin, a polysaccharide, functions in the blood as
an anticoagulant and is found as a coating on medical
tubing and syringes during blood transfusions.