CARBOHYDRATES

Part 2

A lecture prepared by:

Leonisa O. Bernardo, Ph.D.

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 MONOSACCHARIDES

• the simplest carbohydrates

• have backbones of three to seven carbons
• most common and biologically important
monosaccharides:
❑glucose
❑fructose
❑galactose
❑ribose
❑deoxyribose

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GLUCOSE
• most important sugar in the human body
• found in numerous foods
• has several common names
– dextrose
– grape sugar
– blood sugar
• broken down in glycolysis and other pathways to
release energy for body functions.
• What is the normal blood glucose levels of human?
• Since glucose concentration in blood is critical (normal
blood glucose level = 76-106 mg/100 mL),it is controlled
by the hormones insulin and glucagon.
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• When does the highest concentration of glucose
appear?
• after meal
• How does insulin response to excess glucose?
• It stimulates the uptake of excess glucose by most cells
of the body
• What happen to the glucose level after one to two
hours?
• The glucose level return to normal.
• What is the effect of too low glucose concentrations to a
person? What is the role of glucagon when this happen?
• The person feels lightheaded and shaky. The glucagon
stimulates the liver to release glucose into the blood,
reestablishing normal levels.

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• MOLECULAR FORMULA of glucose: C6H12O6
• STRUCTURAL FORMULA:

α-D-Glucose ᵦ-D-Glucose
D-Glucose It exists in cyclic form under
The open-chain form is physiological conditions because the
present in very small carbonyl group at C-1 of glucose
concentrations in cells. reacts with the hydroxyl group at C-5
to give a six-membered ring.
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 CYCLIZATION OF ALDOSE

α-D-Glucose

ᵦ-D-Glucose

HEMIACETAL Page 6
 Fructose
• also called levulose and fruit sugar
• sweetest of all sugars
• found in large amounts in honey, corn syrup, and sweet
fruits.
• MOLECULAR FORMULA: C6H12O6
• STRUCTURAL FORMULA:

α-D-Fructose ᵦ-D-Fructose
D-Fructose
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 CYCLIZATION OF KETOSE

α-D-Fructose

ᵦ-D-Fructose

HEMIKETAL Page 8
 Galactose
• found in biological system as a component of the
disaccharide lactose, or milk sugar; principal sugar found
in the milk of most mammals.
• ᵦ-D-Galactose and a modified form, ᵦ-D-N-
acetylgalactosamine, are also components of the blood
group antigens.
• MOLECULAR FORMULA: C6H12O6
• STRUCTURAL FORMULA:

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 Ribose
• Ribose is a component of RNA and various
coenzymes.
• STRUCTURAL FORMULA:

ᵦ-D-Ribose
D-Ribose α-D-Ribose
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 Deoxyribose

• Component of DNA (the molecule that carries

the genetic information of the cell).
• STRUCTURAL FORMULA:
▪In what way are
ribose and
deoxyribose different
in terms of
structure?

ᵦ-D-2-Deoxyribose ᵦ-D-Ribose ▪Explain the name ᵦ-

D-2-Deoxyribose.
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Test Yourself Question (TYO-2.1)

A. Show the step-by-step cyclization of:

1) D-Fructose.
2) D-Galactose
3) D-Ribose

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 DISACCHARIDES

• consists of two monosaccharides joined

through an “oxygen bridge”.
• Biologically important disaccharides”
– Maltose
– Lactose
– Sucrose

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 MALTOSE
⮚ malt sugar
α-D-Glucose &
⮚ monosaccharides present:
β-D-Glucose

+ H 2O
α-D-Glucose ᵦ-D-Glucose β-Maltose
α(1-4)
Glycosidic bond
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 LACTOSE
⮚ milk sugar
ᵦ-D-Galactose &
⮚ monosaccharides present: ᵦ-D-Glucose

ᵦ(1-4) linkage

+ H 2O
ᵦ-D-Glucose
ᵦ-Lactose
ᵦ-D-Galactose What is the only difference between galactose
and glucose? Page 15
Lactose continued

• Lactose is the principal sugar in the milK

of most mammals.
• To be used by the body as an energy
source, lactose must be hydrolyzed to
produce glucose and galactose (the reverse
of formation of lactose).
• The glucose liberated in the hydrolysis of
lactose is used directly in the energy-
harvesting reactions of glycolysis.

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• Galactosemia is a genetic disease in
humans caused by the absence of one or
more of the enzymes needed for this
conversion.
– A toxic compound formed from galactose
accumulates in people who suffer from galactosemia.
– If the condition is not treated, galactosemia leads to
severe mental retardation, cataracts, and early death.
– However, the effects of this disease can be avoided
entirely by providing galactosemia infants with a diet
that does not contain galactose. Such a diet cannot
contain lactose and therefore must contain no milk or
milk products.

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 Lactose intolerance
• a condition wherein a person cannot hydrolyze lactose
because he does not make the enzyme lactase
– Many adults and some children, like 20 % of US
population, suffer form this.
• Undigested lactose remains in the intestinal tract and
causes cramping and diarrhea that can eventually lead
to dehydration.
– Some of the lactose is metabolized by intestinal bacteria
that release organic acids and carbon dioxide gas into
the intestines, causing further discomfort.
– Lactose intolerance is unpleasant, but its effects can be
avoided by a diet that excludes mild and milk products or
– the enzyme that hydrolyzes lactose can be taken in
tablet form with the dairy products.
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 Sucrose
• table sugar, cane sugar, or beet sugar
• an important carbohydrate in plants.
• used as sweetener;
– considered undesirable because it has no vitamins or
minerals and causes dental caries or cavities.
• water soluble; can easily be transported through
the circulatory system of the plant
• cannot be synthesized by animals
• High concentration of sucrose produce high
osmotic pressure, which inhibits the growth of
microorganisms, so it is used as preservative.
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• Monosaccharides present in sucrose:
– α-D-Glucose & ᵦ-D-Fructose
α-D-Glucose

(α1-ᵦ2)
linkage

+ H2 O
+

ᵦ-D-Fructose Sucrose
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 POLYSACCHARIDES

• Polysaccaride is a large polymer composed of

many monosaccharide units (the monomers)
joined in one or more chains.
• Most carbohydrates found in nature are large
polymers of glucose.
• Important polysaccharides
– Starch
– Glycogen
– cellulose

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 STARCH

• Most carbohydrates that are found in nature are

large polymers of glucose (such as starch).
• principal storage form in most plants.
– These plants store glucose in starch granules. Nearly
all plant cells contain some starch granules, but in
some seeds, such as corn, as much as 80% of the
cell’s dry weight is starch.
• a heterogeneous material composed of the
glucose polymers amylose and amylopectin.

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Amylose
▪ Amylose which accounts for about 20 % of the starch of
a plant cell, is a linear polymer of α-D-glucose
molecules connected by glycosidic bonds between C-1
of one glucose molecule and C-4 of a second glucose
and joined by α(1-4) glycosidic bonds.

▪ A single chain can contain up to four thousand glucose

units.
▪ Amylose coils up into a helix that repeats every six
glucose units Page 23
 Amylose continued

▪ Amylose is degraded by two types of enzymes:

(1) α-Amylase (2) ᵦ-Amylase
▪ They are produced in the pancreas, from which they
are secreted into the small intestine, and the salivary
glands, from which they are secreted into the saliva.
▪ α-Amylase cleaves the glycosidic bonds of amylose
chains at random along the chain, producing shorter
polysaccharide chains.
▪ ᵦ-Amylase sequentially cleaves the disaccharide
maltose from the reducing end of the amylose chain.
▪ The maltose is hydrolyzed into glucose by the
enzyme maltase.
⮚ The glucose is quickly absorbed by intestinal cells and used
by the cells of the body as a source of energy
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Amylopectin
• Amylopectin is a highly branched amylose in
which the branches are attached to the C-6
hydroxyl groups by α(1-6) glycosidic bonds.
The main chains
consist of α(1-4)
glycosidic bonds.

• Each branch contains 20-25 glucose units, and there are so

many branches that the main chain can scarcely be distinguished.
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Amylose and Amylopectin structures

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 GLYCOGEN

⮚ the major glucose storage in animals.

⮚ the structure is similar to that of amylopectin.
✔ The “main chain” is linked by α(1-4) glycosidic bonds,
and it has numerous α(1-6) glycosidic bonds, which
provide many branch points along the chain.
✔ Glycogen differs from amylopectin only by having
more and shorter branches.
⮚ stored in the liver and skeletal muscle.
✔ Glycogen synthesis and degradation in the liver are
carefully regulated.

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COMPARISON IN STRUCTURES OF AMYLOSE,
AMYLOPECTIN AND GLYCOGEN

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 CELLULOSE
A molecule of cellulose typically contains about
3000 glucose units but the largest known
cellulose, produced by alga Valonia, contains
26,000 glucose molecules.

STRUCTURE:

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Cellulose continued

• Cellulose is a structural component of the plant

cell wall.
• The unbranched structure of the cellulose
polymer and the β(1-4) glycosidic linkages allow
cellulose molecules to form long , straight chains
of parallel cellulose molecules called fibrils.
– These fibrils are quite rigid and are held together
tightly by hydrogen bonds; thus it is not surprising that
cellulose is a cell wall structural element.

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Question to Ponder (QP-2.2)

1. In contrast to glycogen, amylose, and amylopectin,

cellulose cannot be digested by humans. Why?
2. Why can other animals, like cows, carabaos, goats, and
termites, digest cellulose?
3. What is the function of cellulose in the human diet?

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Comparison of Starch, Glycogen &
Cellulose

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Page 33
 SUMMARY
DISACCHARIDES/ MONOSACCHARIDES GLYCOSIDIC
POLYSACCHARIDES PRESENT BOND
Maltose α-D-Glucose, β-D-Glucose α(1-4)
Lactose β-D-Glucose, β-D-Galactose β(1-4)
Sucrose α-D-Glucose, β-D-Fructose (α1-β2)

Starch (amylose α-D-Glucose chain: α(1-4)

& amylopectin) branching:α(1-6)

chain: α(1-4)
Glycogen α-D-Glucose branching:α(1-6)

Cellulose β-D-Glucose β(1-4)

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 BLOOD TRANSFUSIONS AND THE
BLOOD GROUP ANTIGENS

Interesting questions on historical background . . .

• What source of blood is used for the first
blood transfusions during the 7th century?
• Were the first trials of transfusions in human
became successful? Describe what happened?
• How did blood transfusions in human become
successful? Describe the experimental methods
involved.
• Why does agglutination occur?
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• Physicians used animal blood to replace human
blood lost by hemorrhages.
– Unfortunately, many people died as a result of this
attempted cure, and transfusions were banned in much of
Europe.
– Transfusions from human donors were somewhat less
lethal, but violent reactions often led to the death of the
recipient, and by the 19th cen., transfusions had been
abandoned as a medical failure.
• In 1904, Dr. Karl Landsteiner performed a series of
experiments on the blood of workers in his
laboratory.
– His results explained the mysterious transfusion fatalities,
and blood transfusions were reinstated as a lifesaving
clinical tool.

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• Landsteiner took blood samples from his coworkers.
– He separated the blood cells from the serum, the liquid
component of the blood, and mixed these samples in test
tubes.
– When he mixed serum from one individual with blood cells
of another, it was observed that, in some instances, the
serum samples caused clumping, or agglutination, of red
blood cells (RBC).

Red blood cells ABO blood typing kit

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 BLOOD TYPING

When antibodies bind to

antigens on the cell
surface, clumping occurs

Landsteiner showed that

there are four human
blood groups,
designated A, B, AB, and
O.

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• Blood typing is a laboratory test that identifies blood
group antigens (substances that stimulate an immune
response) belonging to the ABO blood group system.
• The test classifies blood into four groups designated A,
B, AB, and O.
• Antibody screening is a test to detect a typical antibodies
in the serum that may have been formed as a result of
transfusion or pregnancy.

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Why does agglutination occur?
• The clumping reaction that occurs when
incompatible bloods are mixed in an antigen-
antibody reaction.
• Antigens are large molecules, often portions of
bacteria or viruses, that stimulate the immune
defenses of the body to produce protective
antibodies.
• Antibodies binds to the foreign antigens and
help to destroy them.
• An antibody is a protein produced by lymphocytes (non-granular
white blood cells) that binds to an antigen, facilitating its removal
by phagocytosis (or engulfing by macrophages) or lysis (cell
rupture or decomposition).
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• The differences among blood groups reflect
differences among oligosaccharides
attached to the proteins and lipids of the
RBC membranes.
• The oligosaccharides on the RBC surface
have a common core, consisting of
⮚ β-D-N-Acetylgalactosamine,
⮚ Galactose,
⮚ N-Acetylneuraminic acid (sialic acid), and
⮚ L-Fucose
• It is the terminal monosaccharide of this
oligosaccharide that distinguishes the cells
and governs the compatibility of the blood
type.
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Structure of oligosaccharides on
RBC Surface

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BLOOD GROUP OLIGOSACCHARIDES

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 ACTIVITY

Discuss the following biochemical connections:

1. Low-carbohydrate diets – Estrella
2. Vitamin C is related to sugar - Benitez
3. Fruits, Flowers, Striking Colors and Medicinal
Uses - Chua
4. Tooth decay and sugar – Dela Cruz
5. Type AB as universal recipient and Type O as
universal donor - Baltazar

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THANK YOU FOR YOUR
ATTENTION!

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