BIOCHEMISTRY DEPARTMENT

College of Medicine, UQU

Principle of Biochemistry
2022G – 1444H

CHEMISTRY OF CARBOHYDRATES I
Learning Objectives

By the end of this lecture, students will be able to:

• Illustrate the chemical structure, physical criteria, and

classification of carbohydrates.
• Describe the medical significance of carbohydrates in both
structure and cellular function of body tissues
• Mention the clinical significance of disaccharides digestion and
absorption

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Lecture Outlines

• Food and healthy diet (nutritional pyramid).

• The medical importance of carbohydrates
• Types of Carbohydrates
• Types and nomenclature of monosaccharides and disaccharides
• isomerization of sugars (Stereoisomers, Epimers)
• Glycosides, Amino sugars, Deoxy sugars
• Glycosidic bond and condensation reaction.
• Disaccharide hydrolysis
• Clinical correlations of disaccharides digestion and absorption.

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 Food and Healthy Diet (Balanced Diet)
 A balanced diet means eating a variety of food in the right amounts and in the
healthiest proportions.
 Each food has different nutrients, and each nutrient has its own function in our body.
 Energy intake and nutrient needs are different depending on our age and gender.
 Eating too much or not enough are both bad for our health.
Nutrients – Energy Producing

CB: Caloric Breakdown

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 Nutritional (Food) pyramid
• Nutrients are the substances found in food which drive biological activity, and
are essential for the human body. They are categorized as proteins, fats,
carbohydrates (sugars, dietary fiber), vitamins, and minerals.

• The Food Pyramid is a simple visual representation of how different foods

and drinks contribute towards a healthy balanced diet in order to prevent
obesity, improper nutrition, chronic diseases and dental caries based on
meta-analysis (WHO guidelines).

• the ADA* recommends the Food Guide Pyramid and the Dietary Guidelines
for Americans.
• The five food groups simplify dietary recommendations by focusing on foods
instead of nutrients.
 Each food group plays an important role in an overall healthy eating pattern
(Vegetables, grains, fruits, Dairy, meat and beans, oils). 5
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 CARBOHYDRATES
Carbohydrates are:
 Organic biomolecules abundantly present in the nature.
 Composed of the elements C, H and O.

 General formula: Cn(H2O)n or (CH2O)n

 At least number of carbon atom (n) = 3.

 Found in the cells of plants and animals.

 Produced by photosynthesis in plants.
 Also called saccharides “sugars”.

• Major types of CHO: Monosaccharides, oligosaccharides (di, tri, tetra) and

polysaccharides.
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Importance of carbohydrates

 Carbohydrates are widely distributed both in plants and in animal tissues.

 They are the most abundant biomolecules on Earth.
 Major source of energy from the diet.
 Structural & protective elements in cell walls of bacteria, plants and in
connective tissues.
 Recognition and communication between cells.
 Precursors for other biomolecules (purines, pyrimidines).
 Components of other molecules (nucleosides, nucleotides, coenzymes,
glycolipids ,glycoproteins).

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Types of Carbohydrates

 Monosaccharides are the simplest carbohydrates (i.e., on hydrolysis,

they can not give a simpler form).
 Disaccharides consist of two monosaccharides.
 Polysaccharides contain many monosaccharides.

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 Monosaccharides
 The simplest units of carbohydrate
 i.e., they can not be hydrolyzed to simpler form.

Classification of Monosaccharides
 Aldoses are monosaccharides with an aldehyde
group and many hydroxyl (-OH) groups.
 Ketoses are monosaccharides with a ketone
group and many hydroxyl (-OH) groups.

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Biochemistry Department, college of Medicine, UQU
 Nomenclature of Monosaccharides

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Aldoses
and
Ketoses

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 Stereoisomerism of Monosaccharides
 Stereoisomers: are compounds with the same formula but different in spatial
arrangements due to the presence of asymmetric carbons.

 Asymmetric (Chiral) carbon: a carbon atom attached to 4 different groups.

Any substance
containing
3asymmetric asymmetric
4 asymmetric carbon atom
carbon atoms carbon atoms
shows 2
properties,
A) optical
activity and
 Monosaccharides are chiral compounds (have stereoisomers) thus occur in
B) optical
optically active isomers, except dihydroxyacetone. isomerism.

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Stereoisomerism of Monosaccharides
 Stereoisomers that are mirror images are called Enantiomers (D &L).
 Stereoisomers that are not mirror images are called Diastereoisomers.
 Epimers are diastereoisomers different in only one asymmetric carbon.

Enantiomers Diastereomers Epimers

O O O O O O
H H H H H H
C C C C C C

HO C* H H C* OH HO C* H H C* OH H C* OH HO C* H

H C* OH HO C* H HO C* H HO C* H HO C* H HO C* H

HO C* H H C* OH H C* OH HO C* H H C* OH H C* OH

HO C* H H C* OH H C* OH H C* OH H C* OH H C* OH

CH2OH CH2OH CH2OH CH2OH CH2OH CH2OH

L-glucose D-glucose D-mannose D-galactose D-glucose D-mannose

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 D and L Monosaccharides
• The —OH on the chiral atom
farthest from the carbonyl group is
used to assign the D or L
configuration.
By convention, the letter L is assigned to the
structure with the —OH on the left.
The letter D is assigned to the structure with —
OH on the right.
• The D form is usually the isomer
found in nature.
• D-glucose is the form used in
injection.
Structures of Monosaccharides
1. Fischer Projection
2. Haworth structure (Cyclic Structure)
Carbon (1) in the cyclic structure is the
“new” chiral carbon (Anomeric carbon)

Fischer Projection

( and  Anomers for D-Glucose & Fructose)

The new –OH on C1 is drawn down for the  anomer, and up for the  anomer.

Glucose Anomers Fructose Anomers

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D-Glucose “blood sugar”
• An aldohexose with the formula of C6H12O6.
• The naturally occurring form of glucose found in fruits, corn syrup
and honey.
• It is also known as dextrose, grape sugar, and blood sugar
• It is broken down in cells to produce energy  the principal fuel
for the brain.
• In the liver and other tissues, glucose is converted to all
carbohydrates in the body e.g. glycogen, galactose, ribose and
fructose.

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 Blood Glucose Level
 Glucose known as blood sugar in the body.

 Glucose is the principal fuel for the brain.

 In the body, glucose has a normal blood level of 70-110 mg/dL

• It’s normal concentration in the blood (normal blood glucose) is (70-110 mg/dL).
• Blood glucose above normal range= Hyperglycemia.
• Blood glucose below normal range= Hypoglycemia.

In a glucose tolerance test, blood

glucose is measured for several hours
after ingesting glucose.

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D-Fructose "fruit sugar"
• Is a ketohexose with formula of C6H12O6.
• Is the sweetest carbohydrate.
• Is found in fruit, juices and honey.
• Converts to glucose in the body.
• Fructose is combined with glucose to give sucrose, or
table sugar.
CH2OH
C O
HO C H
H C OH
H C OH
CH2OH

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D-Fructose 19
D-Galactose “In Milk Sugar"
• Is found combined with glucose in the disaccharide lactose,
which is present in milk and other dairy products.
• Is an epimer of glucose at C4.
• Is important in cellular membranes.

D-Galactose

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epimer 20
Reduction of Monosaccharides
 The reduction of the carbonyl group produces sugar alcohols,
or alditols.
 D-Glucose is reduced to D-glucitol also called Sorbitol.

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 CARBOHYDRATES DERIVATIVES

Derivative Group Example

Sugar acids Sugar contain COOH group Gluconic acid, glucuronic

(oxidation) Structure of polysaccharides

Deoxy sugars Removal of O from C2 Deoxy ribose: Structure of nucleic

acids

Amino sugars (NH2) replaces OH at 2nd carbon N-acetyle-glucosamine

Structure of polysaccharides

Sugar alcohol Addition of OH to CHO or CO groups Sorbitol (alcohol of glucose) artificial

(reduction) sweetener

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 DISACCHARIDES
Disaccharides are:
 Formed from two monosaccharides
 Joined by a glycosidic bond
 A condensation reaction:
 glucose + glucose  maltose
 glucose + galactose  lactose
 glucose + fructose  sucrose

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Glycosidic bond.
 Disaccharide is formed when the anomeric carbon (C-1) on one
monosaccharide reacts with hydroxyl group of another monosaccharide to form
a glycosidic bond.
 Linkages may be α or β.
 1-4 linkage: The anomeric carbon is bonded through an oxygen to C4 of
second sugar (Maltose).
 1-2 linkage: The anomeric carbons of the two sugars are bonded through an
oxygen (Sucrose).
 The free anomeric carbon is called reducing end.
 According to the position of the linkage between the sugar units, disaccharides
are classified into non-reducing such as sucrose and reducing such as
maltose and lactose.

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Biochemistry Department, college of Medicine, UQU
 Glycosidic bond and
condensation reaction
C C

C O C O

C C C C

C C C C
OH OH

H2 O

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 Condensation reaction

C C

C O C O

C C 1 4 C C

C C O C C

A disaccharide
1,4 glycosidic bond
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 Maltose (Malt Sugar)
Structure: it Is formed of 2 molecules of -D-glucose molecules
joined by an -1,4-glycosidic bond.

- D-Maltose

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 Maltose (Malt Sugar)
Sources:
a) Malt.
b) Maltose Is produced during the digestion of starch by the
amylase enzyme.

Properties:
Maltose contains a free carbonyl (aldehyde) group, so having
the following properties:
a) It is a reducing agent (can reduce Benedict's reagent).
b) It can be present in α and β forms.
c) It can show mutarotation.

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 Lactose (Milk Sugar)
Structure: It Is formed of 2 molecules of -glucose and -
galactose linked by a -1,4-glycosidic bond.

- D-Lactose

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 Lactose (Milk Sugar)
Sources:
It is the sugar present in milk. In human milk, its concentration is 7.4 g/dl.
It may appear In urine in late pregnancy and during lactation.
Properties:
lactose contains a free carbonyl group, so having the following
properties:
a) It is reducing sugar (can reduce Benedict's reagent).
b) It can be presented in α and β forms.
c) It can show mutarotation.
d) Lactose Is digested by an intestinal enzyme called: lactase into
galactose and glucose.

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 Sucrose (Table Sugar)
 Structure: it is formed of 2 molecules of α-glucose and β-
fructose molecules joined by ,-1,2-glycosidic bond.

α, -1,2-glycosidic bond
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 Sucrose (Table Sugar)
Sources:
cane and beet sugar.
It is also present in pineapple and carrot.
Properties:
sucrose contains no free carbonyl group (because both the anomeric
carbons; carbon 1 of α-glucose and carbon 2 of β-fructose are involved in
glycosidic bond) so fructose has the following properties:
a) It is not a reducing sugar (cannot reduce Benedict's reagent).
b) It cannot be present in α and β forms.
c) It cannot show mutarotation.
d) Sucrose is dextrorotatory. On hydrolysis by invertase (sucrase) enzyme, it
gives a mixture of equal number of glucose and fructose molecules. This
mixture is called invert sugar and it is levorotatory.

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 Disaccharide Synthesis

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Disaccharide Hydrolysis
Disaccharide hydrolyzed to its corresponding of
monosaccharides.
Maltose + H2O Glucose + Glucose
Lactose + H2O Glucose + Galactose
Sucrose + H2O Glucose + Fructose

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 Disaccharides Comparison
Maltose Lactose Sucrose

Composition - Glucose + - Glucose  -Galactose + - α-D-glucose + β-D-

Glucose fructose
Bond 1,4-glycosidic bond  1,4-glycosidic bond ,-1,2-glycosidic

Reduction Reducing sugar Reducing sugar Non-reducing sugar

property
Anomeric C Free Free No free anomeric C

Mutarotation , anomers , anomers No  or  anomers

Hydrolysis by Maltase Lactase Sucrase

Source Enzymatic hydrolysis of Milk Cane sugar, beet sugar,

starch and malt by Table sugar
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 Disaccharidase deficiencies
Lactose intolerance
Disaccharidase deficiencies are caused by the decreased hydrolysis of
the disaccharides by the disaccharidase enzymes* (lactase; maltase;
sucrase).

Lactose intolerance is the inability to digest

lactose, It is caused by a shortage of lactase in
the body, an enzyme produced by the small
intestine that is needed to digest lactose.

This leads to milk fermentation by intestinal

bacteria, diarrhea and abdominal distension
(Lactose intolerance).
While lactose intolerance is not dangerous, its
symptoms
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