CARBOHYDRATES Carbohydrate Structure

What is unique about the structure of sugars?

Carbohydrates are
 A major source of energy from our diet. Monosaccharide can be;
 Composed of the elements C, H, and O. A. Aldose – a polyhydroxy aldehyde a sugar that contains an
 Also called saccharides, which means “sugars.” aldehyde group as part of its structure

Carbohydrates B. Ketose – a polyhydroxy ketone a sugar that contains a

 Are produced by photosynthesis in plants. ketone group as part of its structure
 Such as glucose are synthesized in plants from CO2,
H2O, and energy from the sun. Aldoses
 Are oxidized in living cells (respiration) to produce CO2,  Aldoses are monosaccharides
H2O, and energy.  With an aldehyde group.
 With many hydroxyl (─OH) groups.
FUNCTONS triose (3 C atoms)
 1. It serves as a backbone of other molecules. tetrose (4 C atoms)
 2. It serve as a stored energy (such as starch, cellulose, pentose (5 C atoms)
and glycogen). hexose (6 C atoms)
 3. It is the most common source of energy in the body.
 It combines with proteins (glycoproteins and Ketoses
proteoglycans) to form structural components of living  Ketoses are monosaccharides
cells.  With a ketone group.
 With many hydroxyl (─OH) groups.
CLASSIFICATIONS triose (3 C atoms)
 1. Monosaccharides – simple sugar that consist of only tetrose (4 C atoms)
one sugar molecule. C6H12O6. pentose (5 C atoms)
 compounds that contain a single carbonyl and two or hexose (6 C atoms)
more hydroxyl groups
 2. Disaccharides – composed of two more sugar
molecules

 Oligosaccharides – sugars linked by glycosidic bonds

 Polysaccharides – a complex form of carbohydrates that

consist of three or more monosaccharide molecules

Types of Carbohydrates A. aldohexose

The types of carbohydrates are
 Monosaccharides, the simplest carbohydrates. B.
 Disaccharides, which consist of two monosaccharides. Ketopentose
 Polysaccharides, which contain many monosaccharides.
Classification of Carbohydrates.
I. Number of carbohydrate units
 monosaccharides: one carbohydrate unit (simple
carbohydrates)
 disaccharides: two carbohydrate units (complex
carbohydrates)
 trisaccharides: three carbohydrate units
 polysaccharides: many carbohydrate units

Monosaccharides
Monosaccharide consist of
 3 to 6 carbon atoms, typically. (C6H12O6)
 A carbonyl group (aldehyde or ketone).
 Several hydroxyl groups.
MONOSACCHARIDES β-GALACTOSE and β-FRUCTOSE-
β – CARBOHYDRATES, the OH group of C1 is pointing in
the same direction as the CH2OH

α- GLUCOSE

 Carbohydrates: Structures of Monosaccharides

Monosaccharides Chiral (asymmetric) – carbon atoms is the usual source
 α-GLUCOSE – α-carbohydrates, the OH group of C1 is of optical isomerism
pointing in the opposite direction to the CH2OH.
 Two forms of glyceraldehyde are designated by
 GLUCOSE or dextrose or blood sugar. Both found in D- glyceraldehyde and L- glyceraldehyde
vertebrates and invertebrates
 stereoisomers (optical isomers) – molecules that differ
from each other only in their configuration (3-D shape).
 enantiomers (mirror – image, nonsuperimposable
stereoisomers

Fischer Projections
A Fischer projection
 Is used to represent carbohydrates.
 Places the most oxidized group at the top.
 Shows chiral carbons as the intersection of vertical and
horizontal lines.
α-GLUCOSE

β-GALACTOSE and β-FRUCTOSE

D and L Notations
In a Fischer projection, the −OH group on the
 Chiral carbon farthest from the carbonyl group
determines an L or D isomer.
 Levo - Left is assigned the letter L for the L-isomer.
 Dextro - Right is assigned the letter D for the D-isomer
 Most naturally occurring carbohydrates are of the D-
configuration.
D-Glucose
D-glucose is
 Found in fruits, corn syrup, and honey.
 An aldohexose with the formula C6H12O6.
 Known as blood sugar in the body.
 The monosaccharide in polymers of starch, cellulose,
and glycogen.

Blood Glucose Level

In the body,
 Glucose has a normal blood level of 70-90 mg/dL.
 A glucose tolerance test measures blood glucose for
several hours after ingesting glucose.
D-Fructose Cyclic Forms of Carbohydrates: Furanose Forms
D-fructose  Cyclization of carbohydrates to the hemiacetal creates a
 Is a ketohexose C6H12O6. new chiral center. The hemiacetal or hemiketal carbon of
 Is the sweetest carbohydrate. the cyclic form of carbohydrates is the anomeric carbon.
 Is found in fruit juices and honey. Carbohydrate isomers that differ only in the
 Converts to glucose in the body.

D-Galactose
D-galactose is
An aldohexose C6H12O6.
Not found free in nature.
Obtained from lactose, a disaccharide.
A similar structure to glucose except
for the –OH on C4.

Draw the Fischer Projection of D-

Fructose

stereochemistry of the
anomeric carbon are called anomers.

Converting Fischer Projections to Haworth formulas

Cyclic Haworth Structures

Cyclic Structures of Monosaccharides
Stable cyclic hemiacetals form
 When the C=O group and the —OH
are part of the same molecule.
 For hexoses, the hydroxyl group on C-
5 reacts with the aldehyde group or
ketone group.
 The cyclic structure of a D-isomer has
the last CH2OH group located above
the ring.

Drawing the Cyclic Structure for Glucose

What happens if sugar forms a cyclic molecule?
 The cyclization takes place as a result of interaction
between the functional groups on distant carbons, such
as :
a. C-1 and C-5, to form a cyclic hemiacetal (in aldoses)
b. interaction between C-2 and C-5, to form a cyclic
hemiketal (in ketohexoses)
 Carbonyl carbon becomes new chiral center called
anomeric carbon

Cyclic Structures
Cyclic structures
 Are the prevalent form of monosaccharides with 5 or 6
carbon atoms.

O O

 Form when the hydroxyl group on C-5 reacts with the

aldehyde group or ketone group.
 Learning Check
23.7: Cyclic Forms of Carbohydrates: Pyranose Forms. Write the cyclic form of -D-galactose

Note: the pyranose forms of carbohydrates adopt chair

conformations.

-D-Glucose and β-D-Glucose in Solution

When placed in solution,
 Cyclic structures open and close.
 -D-glucose converts to β-D-glucose and back.
 There is only a small amount of open chain

Chemical Properties of Monosaccharides
Reducing Sugars
Reducing sugars
 Are monosaccharides with a carbonyl group that
oxidizes to give a carboxylic acid.
 Undergo reaction with Benedict’s reagent (Cu2+) to give
the corresponding carboxylic acid.
 Include the monosaccharides glucose, galactose, and
fructose.
Reduction of Monosaccharides
The reduction of monosaccharides
 Involves the carbonyl group.
 Produces sugar alcohols called alditols.
 Such as D-glucose gives D-glucitol also called sorbitol.
Learning Check
Write the products of the oxidation and reduction of
D-mannose.
Epimeric Pair
 Epimer: One of a pair of stereoisomers that differ in the
absolute configuration of a single stereocenter. When the
molecule has only one stereocenter then the epimers are
enantiomers.
 Example:
 D-Galactose is an epimer of D-glucose because the two
sugars differ only in the configuration at C-4 .
 D-Mannose is an epimer of D-glucose because the two
sugars differ only in the configuration at C-2 .
 When a molecule such as glucose converts to a cyclic
form, it generates a new chiral centre at C-1 .
Epimeric Pair
Disaccharides
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 is known as a glycosidic
bond.
 Glycosidic bonds (also called glycosidic linkages) can be
of the alpha or the beta type.
 Disaccharides (C12H22O11)
Disaccharide consist of of two more sugar molecules
Learning Check
Write the structures and names of the two monosaccharides
that form when sucrose is hydrolyzed.

Sweeteners
 Sugars and artificial sweeteners
 Differ in sweetness.
 Are compared to sucrose (table sugar), which is
assigned a value of 100. Oligosaccharides
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
Starch is the stored form of sugars in plants and is made up of
a mixture of amylose and amylopectin (both polymers of
glucose).
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

Polysaccharides
 Are polymers of D-glucose.
 Include amylose and amylopectin,
starches made of α-D-glucose.
 Include glycogen (animal starch in
muscle), which is made of α-D-
glucose.
 Include cellulose (plants and wood),
which is made of
β-D-glucose.
Glycogen
 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..