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Definition

Carbohydrates literally mean hydrates of •


carbon.
carbon •
and
hydrates ( water). •
Because it was thought to have the molecular •
formula (CH2O)n, the ratio of H to O as in water
(H2O) hence the name.
Now known that not all carbohydrates obey •
this rule. (e.g,derivative)
Biochemical Definition
Carbohydrates are poly-hydroxy carbonyl
compounds (aldehyde or ketone) and their
derivative and the polymer that give them on
hydrolysis
Example:
BIOMEDICAL IMPORTANCE
 Carbohydrates have important
structural and metabolic roles.
 Glucose is the most important
carbohydrate

most dietary carbohydrate is absorbed into


the blood stream as glucose.

 Glucose is the major metabolic fuel of


mammals
a universal fuel of the fetus
Biomedical Importance of Carbohydrates
1- Energy source for plants and animals
(glucose).
One of the major source of energy in cell.
75% of energy in cell comes from CHO.
25% from others (fats)
1 g CHO =4 K.calories
1 g protein =4 K.calories.
1 g lipid =9K.calories.

Why body not use lipid as major energy source


instead of CHO?
2- Cell membrane components:
eg. Glycolipid and glycoprotein

3- Form structural tissues in plants and


in microorganisms
eg. (cellulose, chitin, murein)
4- Glucose is the precursor for
synthesis of all other carbohydrates in
the body, including
Galactose in lactose of milk.
Glycogen for storage; .
Store as glycogen in animals, and starch
In plants. (storage form of energy).
Why the cell store excess glucose as glycogen?

Ribose and Deoxyribose in nucleic acids;


DNA –deoxy ribonucleic acid (deoxy sugar)
RNA –ribonucleic acid (ribose sugar). .

5-To describe the mechanism of some


diseases related to CHO.
eg.Diabetes Mellitus.
lactose intolerance, Glycogen storage diseases
glactosemia .
,
Classification of Carbohydrates
Carbohydrates are classified into four groups:

1.Monosaccharides: (saccharides means


sugars)that cannot be hydrolyzed into simpler
carbohydrates, (Exp. Glucose).
2.Disaccharides: condensation products of two
monosaccharide units (Exp. Lactose).

Note, all mono and disaccharides have the


ending ose (glucose, galactose, ribose,
lactose, etc…)
Classification of Carbohydrates
3.Oligosaccharides are condensation products
of three to ten monosaccharides;
Maltotriose is an example.
4.Polysaccharides are condensation products
of more than ten monosaccharide units
(Exp. Glycogen & Starch).
Monosaccharides are classified •
by:
1- the number of carbon atoms: •
3C-Triose , 4C -tetroses , 5C-pentoses , 6C- •
hexoses and 7C – heptoses.

2-the position or type of carbonyl group:


Aldehyde, aldose (terminal)
Ketone, ketose (middle ).
3- Both number of carbon atom and type of
carbonyl
E,g Aldotriose and Ketotriose
Monosaccharides are classified by:
1- the number of carbon atoms:
Aldose sugars
H H H H H

C O C O C O C O C O

(H C OH)n H C OH H C OH H C OH H C OH

CH2OH CH2OH H C OH H C OH H C OH

Aldose Aldotriose CH2OH H C OH H C OH


n=1
Aldotetrose CH2OH
n=2 H C OH
Aldopentose
CH2OH
n=3
Aldohexose
n=4
Ketose sugars
CH2OH CH2OH
CH2OH
CH2OH
C O C O CH2OH
C O
C O
(H C OH)n H C OH C O
H C OH
CH2OH
CH2OH H C OH H C OH
CH2OH
CH2OH H OH
Ketose Ketotriose Ketotetrose
n=1 Ketopentose H C OH
n=0
n=2
CH2OH
Ketohexose
n=3
Monosaccharides
Glucose Structure
The structure of Glucose can be represented in three
ways:

Straight Chain Form Haworth Projection Chair Form


Cyclic Fischer
Haworth Projection Projection of a-D-
of a-D-Glucose Glucose
Almost all monosaccharides (except 
dihydroxy acetone DHA )contain at least 
one asymmetrical carbon atom (chiral centre)
and are, therefore,have optical activitity
(ability to rotate plane polarized light) and
optical isomers.

The number of isomers is obtained by the 


formula 2n
n=No of asymmetric carbons atom.
Monosaccharides
Forms of Isomerism
Monosaccharides exhibit various forms of isomerism:
Because it have asymmetric carbon atom

D and L Enantiomers.

Pyranose and Furanose ring structures.

Alpha and Beta anomers.

Epimers.

Aldose and Ketose isomerism.

Optical activity
1- D & L isomers (enantiomers)

Those monosaccharides that are of physiological 


significance exist in the D-configuration, where the
hydroxyl group is on the right side .

The mirror-image, called enantiomers, are in the L-


configuration.

They are related to glyceraldehyde which exists in 


two isomers D and L
Monosaccharides
L and D Enantiomers
It also called mirror images or Optical Isomers:
Monosaccharides can exist in 
either of two configurations, as
determined by the orientation of the
hydroxyl group about the
asymmetric carbon farthest from
the carbonyl group.
e,g D & L form of glucose is 
determine by carbon 5.
Monosaccharides
L and D Enantiomers
2-pyranose and furanose ring
(isomer)
Monosaccharide with 5 or 6 carbon atoms tend to
cyclyze in solution.
This terminology indicate that the ring structure of
monosaccharide is similar to either pyran or
furan
Monosaccharides
2-Pyranose and Furanose
3 - α- and β anomers.(isomers)
Isomers that differ on the position of OH
group around anomeric carbon (which was
carbonyl carbon) when the ring is formed.
Monosaccharides
3-Alpha and Beta Anomers
3-EPIMERS (ISOMERS)
Two monosaccharide that differ from each other
by position of OH group on one carbon. ( eg
carbon 2,3 and 4 of glucose).

glucose and glactose ar epimers at carbon 4

While glucose and mannose are carbon 2


epimers.
Monosaccharides
Epimers

Mannose Glucose Galactose


Monosaccharides
5-Aldose and Ketose Isomerism
Optical activity

The ability to rotate plane-polarized light to •


the right (dextrorotatory) +sign

Or to the left (levorotatory) - •


sign
Glucose is dexrtoratotry hence the name •
dextrose in clinical practice eg IV fluid •
Fructose is levorotatory hence the name •
levulose
Monosaccharides
Physiological Importance
 Pentoses of Physiologic importance
Ribose inter the structure of Nucleic Acids

Ribose Deoxyribose
Monosaccharides
Physiological Importance
• Hexoses of Physiologic importance:
 Glucose .

 Fructose

Galactose .
D-glucose
Common names: •
glucose, grape sugar, dextrose •
Natural Source: •
Fruits,,cereal starch hydrolysis, sugar •
hydrolysis, corn syrup and honey. •
Importance: •
the sugar of the body, the principal one used by the •
tissue.
Building block for: disaccharides (such as sucrose, •
lactose and maltose) and polysaccharides (starch,
cellulose and glycogen) converted to ribose and
deoxyribose for DNA and RNA synthesis.
D-galactose
Natural Source: •
None for free form •
Formed by hydrolysis of lactose (milk sugar). •
Importance: converted to glucose, and used for •
the synthesis of Milk.
enter in cellular membranes of brain & •
nervous system.
Deficiency diseases: •
Galactosemia: •
Enzyme to metabolize galactose missing and •
levels build in blood cause mental retardation,
cataracts and cirrhosis.
D-fructose
Common names: •
Levulose and fruit sugar •
Natural Source: •
Fruit juice and honey •
Hydrolysis of cane and beat sugar •
Importance: converted to glucose in liver, •
source of energy for spermatozoa
Due to sweetness, used as sweetener. •
Monosaccharides derivative
1-Amino sugar (replacement of one hydroxyl group •
by amino group e.g, glucose amine (in glycoprotein
and glycolipid and glycosaminoglycan a
heteropolysaccharide erythromicine(antibiotic)
2- Phosphate ester in metabolism. •

3- Oxidation of glucose at carbon one give (aldonic) •


gluconic acid this is the bases of Benedict and
Fehling ,reaction in detection of glucose in urine the
sugars are called reducing sugar.
When the anomeric cabon form bond with another •
molecule the sugar is non reducing
. •
while oxidation at carbon 6 give (uronic) •
glucuronic important in detoxification reaction
and in glycosaminoglycan a
heterpolysaccharide
4- Reduction of glucose at carbon one give •
sugar alcohol sorbitol (which in high level as in
diabetic leads to cataract formation)
Glycosides
Glycoside is two substances connected by
glycosidic bond.
Importance:
1- formation of disaccharide and other
derivative.
2- cardiac glycoside (is a drug used in
treatment of some heart disease)by
inhibiting Na-K ATPase pump. e.g Digitalis
&.Auobain (contain sugar and steroid)
3-Certain antibiotic like streptomycin.
Disaccharides

The physiologically important disaccharides are

Maltose , Sucrose, and Lactose:


Disaccharides
Formation
Disaccharides
Maltose
Maltose : Malt sugar, composed exclusively of •
glucose, found in germinating cereals and
malts
The major degradation product of starch, is •
composed of 2 glucose monomers in an α-(1,4)
glycosidic bond.
. •

Give Glucose + glucose by maltase enzyme. •

. •
Disaccharides
Maltose
Disaccharides
Sucrose
Sucrose: table sugar, found in cane and beat •
sugar
composed of glucose and fructose through •
an α-(1,2)b-glycosidic bond.
give Glucose + fructose by sucrase •
enzyme(invertase) because the product of its
hydrolysis (known as invert sugar) invert
optical activity from dextro to levorotatory.
Disaccharides
Sucrose
Disaccharides
Lactose
Lactose: Milk sugar , is found exclusively in
the milk of mammals and consists of
galactose and glucose in a β-(1,4) glycosidic
bond
give Glucose + galactose by lactase enzyme •
Disaccharides
Lactose
Lactose Intolerance
Symptoms •
Bloating, abdominal discomfort, and •
diarrhea
Causes •
Lactase deficiency •
Oligosacchrides •
Usually not found free but in the form of •
glycoprotein and glycolipid.few e,g
maltotriose and raffinose.
Sucrose: prevalent in Lactose: is found
sugar cane and exclusively in the
sugar beets, is milk of mammals and
composed of
consists of galactose
glucose and fructose
through an α-(1,2)b- and glucose in a β-
glycosidic bond. (1,4) glycosidic bond
Maltose: the major degradation
product of starch, is composed
of 2 glucose monomers in an α-
(1,4) glycosidic bond.
Classification of polysaccharide •

When polysaccharides are composed of a single •


monosaccharide building block, they are termed
homopolysaccharides.

They are Branched or unbranched •


Storage or structural •

Polysaccharides composed of more than one type •


of monosaccharide are termed
heteropolysaccharides
Polysaccharides
Types
Polysaccharides
Starch
 Is a homopolymer of Glucose. (storage form of
CHO in plant)
 It is the most abundant carbohydrate in cereals,
potatoes, and other vegetables .
 The two main constituents are amylose (15–20%),
which has a non-branching helical structure.
 and amylopectin (80–85%), which consists of
branched chains composed of 24–30 glucose
residues united by 1 → 4 linkages in the chains
and by 1 → 6 linkages at the branch points.
Polysaccharides
Starch (Amylopectin)
Polysaccharides
Glycogen
 Is the storage polysaccharide in human.
 Is a highly branched than amylopectin
Glycogen is the major form of stored •
carbohydrate in animals.

It is a homopolymer of glucose in α-(1,4) •


linkage;

it is highly branched, with α-(1,6) branch •


linkages occurring every 8-11 residues.
Glycogen is a very compact structure . •

This compactness allows large amounts of •


carbon energy to be stored in a small volume,
with little effect on cellular osmolarity.
Glycogen is primarily stored in liver and muscles. •

Liver glycogen contributes to maintenance of •


blood glucose level

Muscle glycogen is used as readily available •


source of energy within muscles during exercise
Polysaccharides
Glycogen (General Structure)
Polysaccharides
Glycogen (Branch Point)
Polysaccharides
Others
Inulin is a homopolysaccharide of
fructose, linked by β(1-2) glycosidic
bond.
 found in tubers and roots of artichoke
( used for assessment of glomerular
filtration rates .
 Cellulose: is the chief insoluble constituent of
plants framework.
 It consists of β-D-glucopyranose units linked by
β(1 → 4) bonds to form long, straight chains.

 Cellulose cannot be digested by human because


of the absence of an enzyme that hydrolyzes the
β linkage.

 There is limited bacterial metabolism of cellulose


in the human colon
 It is an important source of “bulk” and Fibers in
the diet (which attract water and soften stool
hence prevent constipation)
Heteropolysaccharide
Polysaccharides composed of more than one •
type of monosaccharide are termed
heteropolysaccharides •
E.g,Heparin (anticoogulant) •
Hyluronic acid Keratan and Dermatan sulfate •
in extracellular matrix of connective tissue and
synovial fluid