CHEMISTRY AND BIOLOGICAL ROLE OF CARBOHYDRATES IN … · 2020. 1. 27. · CHEMISTRY AND BIOLOGICAL...
Transcript of CHEMISTRY AND BIOLOGICAL ROLE OF CARBOHYDRATES IN … · 2020. 1. 27. · CHEMISTRY AND BIOLOGICAL...
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CHEMISTRY AND BIOLOGICAL
ROLE OF CARBOHYDRATES
IN THE BODY-II
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LECTURE OUTLINE
By the end of the lecture, the student should
know:
The formation of the ring structure.
The glycosidic linkage.
The functions and biological importance of
polysaccharides.
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THE FORMATION OF THE RING
STRUCTURE
Sugar molecules that have five or six carbons
are flexible.
If a six member sugar forms a ring between
Carbon 1 and Carbon 5, it is called a pyranose
ring
If a six member sugar forms a ring between
Carbon 1 and Carbon 4 it is called a furanose
ring. (Also if the ring is formed between Carbon
2 and 5 in keto sugars)
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The flexible carbons in monosaccharides like
glucose or fructose bring Aldehyde or Ketone
Group close to the OH group of the same
molecule and form a ring structure.
If this ring is formed by an aldehyde group, it is
called “Hemiacetal ring” or if it is formed by a
keto group, it is called “Hemi Ketal Ring”
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The aldehyde
group comes in
close proximity
to the hydroxyl
group.
The H of the
hydroxyl group
is transferred to
the oxygen of
the aldehyde
group.
The oxygen
from the
hydroxyl group
forms a bond
with the carbon
of the aldehyde
group.
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GLYCOSIDES
Glycosides are compounds in which:
A Monosaccharide is attached to an
Alcoholic group of a second compound By
Glycosidic Linkage.
Glycosidic Linkage is Defined as an:
Acetal Linkage Between Carbonyl Carbon
of a Monosaccharide and Hydoxyl Group of
an Another Compound.
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METHYL GLUCOSIDE
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IN GLYCOSIDES OTHER COMPOUND MAY OR MAY
NOT BE A MONOSACCHARIDE
When the alcoholic compound in a
Glycoside is a Non-Carbohydrate it is
called Aglycon.
In methyl Glucoside Methyl group is an
Aglycon.
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IN METHYL GLUCOSIDE
METHYL GROUP IS AN
AGLYCON
H- C------O H-C-OH OH-C-H H-C-OH H-C-OH CH2OH
CH3
Methyl Glucoside
Glycon
Aglycon
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GLYCOSIDES
Carbonyl Carbon of a Monosaccharide is attached, by an Acetal linkage, to an Alcoholic group of a second compound.(Acetal is an organic molecule where two separate oxygen atoms are single bonded to a central oxygen atom)
H- C=O H-C-OH OH-C-H H-C-OH H-C-OH CH2OH
OH CH3
Methyl Glucoside
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HEMIACETAL AND ACETAL
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GLYCOSIDIC LINKAGE BEING FORMED
BETWEEN TWO SUGARS
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GLYCOSIDIC LINKAGE BEING FORMED
BETWEEN TWO SUGARS
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Types of Glycosidic Linkages
In the formation of disaccharides, the
type of glycosidic linkage formed is O
Glycosidic Linkage.
There are other glycosidic linkages as
well which include S-glycosidic bonds,
N- Glycosidic bonds.
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POLYSACHHARIDES
Most of the Carbohydrates found in nature
occur in the form of high molecular weight
complex compounds called
POLYSACCHARIDES.
Composed of ten or more monosaccharides
or their derivatives.
Monomer units are linked by the glycosidic
(acetal) linkages.
On Hydrolysis yield a large number of
Monosaccharide units or their derivatives.
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POLYSACCHARIDE MAY BE CLASSIFIED INTO
TWO GROUPS
When polysaccharides are composed of a single type of monosaccharide building block, they are termed:
Homo polysaccharides or (Homo Glycans).
Polysaccharides composed of more than one type of monosaccharide are termed:
Hetero polysaccharide or (Hetero Glycans).
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HOMOPOLYSACCHARIDES:
POLYSACCHARIDES MAY BE COMPOSED OF A
SINGLE TYPE OF MONOSACCHARIDES
Or it may be composed of
more than one type of Units
G G G G G G G G G
AG GA AG GA AG GA AG GA
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HOMOPOLYSACCHARIDES
Polysaccharides which are composed of
Similar Types of Monosaccharide Units.
Common examples are:
Starch.
Glycogen.
Cellulose.
Dextrin.
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TWO TYPES OF GLYCOSIDIC LINKAGES IN
GLUCOSE POLYMERS:
1-4, Glycosidic Linkage.
1-6, Glycosidic Linkage (Branch
Point)
1
4
1
4
1
4
1
4
6
1 4
1 1
4
1
1
4
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STARCH:A COMPLEX GLUCOSE POLYMER
It is a homopolysaccharide comprising of molecules of glucose joined together by alpha 1,4 and alpha 1,6 linkages.
It is made up of two polysaccharide units.
AMYLOSE
AMYLOPECTIN
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Amylose:
Straight Chain of Glucose molecules.
Having Only 1-4, Glycosidic Linkages.
Amylopectin:
Complexed & highly Branched Polymer of Glucose.
Having Both 1-4 & 1-6, Linkages.
Linear Segment with 1-4 Linkage.
1-6, Linkages at Branch Points.
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ALPHA 1-4 LINKAGE
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ALPHA 1-6 LINKAGE
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AMYLOSE; UNBRANCHED GLUCOSE POLYMER
Straight chain of Glucose molecules.
Several thousands of Glucose units (In the range
of 300 and 3000).
1→4 Glycosidic bonds.
1
4
Reducing End
Non-reducing End
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AMYLOPECTIN; COMPLEXED & HIGHLY
BRANCHED POLYMER OF GLUCOSE.
Having Both 1-4 (Linear Segment) & 1-6,
Linkages (Branch Points).
Branching takes place with (1 6) bonds
occurring every 24 to 30 glucose units.
Formed of 2,000 to 200,000 glucose units.
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STARCH IS A COMPLEX OF TWO TYPES OF
GLUCOSE POLYMERS
Unbranched highly coiled Amylose
Highly branched uncoiled Amylopectin
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STARCH; MIXTURE OF TWO COMPLEX
CARBOHYDRATES
Amylose
Forms about
25% of starch
molecule.
Unbranched
Highly coiled
Amylopectin
Forms about
75% of starch
molecule.
Highly branched
Uncoiled.
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STARCH; DIETARY SOURCES
In human diet Starch is
commonly obtained from:
Cereals (Rice, Wheat, and
Corn)
Potatoes and sweet potato.
Fruits such as Banana.
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STARCH: BIOLOGICAL SIGNIFICANCE
Major form of stored carbohydrate in plant cells.
Plants store starch within specialized organelles called Amyloplasts.
When energy is needed for cell work, the plant hydrolyzes the starch releasing the glucose.
Humans also have enzymes to hydrolyze (Digest) starch.
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Principle dietary carbohydrate.
In terms of human nutrition, starch is by far the most important of the polysaccharides.
It constitutes more than half the carbohydrates even in many affluent diets, and much more in poorer diets.
Major source of Glucose (Metabolic fuel).
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DEXTRINS ARE
PARTIALLY HYDROLYSED STARCH
Intermediate products of hydrolysis of starch
by acids or Amylase.
Similar to starch but less complex and having
lower molecular weight.
Dextrin occurs in all starch producing parts of
plants as an intermediate of starch synthesis
or break down.
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GLYCOGEN
Polymer of about 60,000 Glucose residues.
Structure similar to Starch, but is even more compact & highly branched.
This compactness allows large amounts of energy to be stored in a small volume, with little effect on cellular osmolarity.
Glycogen is the analogue of starch in plants, and is commonly referred to as animal starch.
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GLYCOGEN; BIOLOGICAL SIGNIFICANCE
Major form of storage of carbohydrates
(energy store) in animal liver and
muscles
Primary short term energy storage.
Forms an energy reserve that can be
quickly mobilized to meet a sudden
need for glucose (Energy)
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ONLY THE LIVER GLYCOGEN IS THE
SOURCE OF BLOOD GLUCOSE AND MADE
AVAILABLE TO OTHER ORGANS
Although the total amount of Glycogen in
muscles exceeds that in liver, Only the
stores in the liver can be made accessible to
other organs.
Muscle glycogen provides Glucose
(Metabolic fuel) to muscles only during
exercise.
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CELLULOSE DISTRIBUTION
Most abundant organic compound in the earth's biosphere is in cellulose.
Cellulose is the primary structural component of green plants.
The primary cell wall of green plants is made of cellulose.
Wood is largely cellulose, while paper and cotton are nearly pure cellulose.
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CELLULOSE STRUCTURE;
STRAIGHT, UNBRANCHED AND UNCOILED CHAIN
OF GLUCOSE
Glucose Polymer:
500 to 5000 Glucose units.
Glucose units linked by β(1→4)-glycosidic bonds.
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CELLULOSE; BIOLOGICAL SIGNIFICANCE
It is a structural polysaccharide.
The peculiar long fiber like structure
contributes to their high tensile strength.
Due to high tensile strength it is important
in cell walls, where they provide rigidity to
plant cells.
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NUTRITIONAL VALUE OF CELLULOSE IS
INSIGNIFICANT IN HUMAN BEINGS
Humans and many other animals lack an
enzyme (Cellulase) to break the beta-
linkages, so they do not digest cellulose.
In the diets of humans Cellulose functions
as roughage and is eliminated largely
unchanged.
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CELLULOSE; CLINICAL SIGNIFICANCE
Cellulose is not digestible by humans and is often referred to as 'Dietary fiber' or 'Roughage’.
Roughage acts as a bulking agent that increases the intestinal motility and helps propagating intestinal contents.
Dietary Cellulose therefore prevents Constipation.
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HETROPOLYSACCHARIDES MAY BE CLASSIFIED IN
THREE MAJOR GROUPS
Mucopolysaccharides.
Mucilages
Hemicellulose
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MUCOPOLYSACCHARIDES
Composed of:
Amino Sugars and
Uronic Acids.
Important examples are:
Hyaluronic Acid
Chondrotin
Heparin.
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HYALURONIC ACID AND CHONDROTIN
ARE IMPORTANT COMPONENTS OF
INTERCELLULAR MATRIX
Intercellular Matrix is the organic material
filled in the intercellular spaces (So Called
Ground substance).
This organic matter is composed mainly of:
Collagen (Protein) and
Mucopolysaccharides.
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INTERCELLULAR MATRIX
(GROUND SUBSTANCE) PLAYS MANY
IMPORTANT AND VITAL ROLES:
Cementing and strengthening substance for the
tissue cells.
Protective Barrier for the tissues.
Holds the extracellular water and electrolytes in a
homogenous distribution in the body.
Intercellular Matrix is the
Protective Barrier for the tissues.
Any living or non living injurious substance when
penetrates the tissue, they have to pass through the
ground substance to reach the cells.
The ground substance prevents the penetration of
bacteria or any injurious agent in the tissue.
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MAJOR MUCOPOLYSACCHARIDES OF GROUND
SUBSTANCE ARE:
Hyaluronic acid in soft tissues
Chondrotin in hard tissues.
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HYALURONIC ACID
Long chain of alternate molecules of:
Glucuronic Acid And
N Acetyl Glucosamine.
Hyaluronic Acid is Principally Found in Ground
Substance Of the Soft Tissues e.g. Skin,
Muscles, Liver and Synovial Fluid.
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BIOLOGICAL IMPORTANCE OF HYALURONIC
ACID.
Being the component of ground substance
It has a significant contribution in all the
vital functions of Intercellular Matrix.
Lubrication of Joints.
Hyaluronic acid present in the synovial
joint spaces acts as lubricant and shock
absorber.
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CHONDROTIN
Mainly present in the Ground Substance of
Bone and Cartilage.
Polymer of N Acetyl Galactoseamine and
Glucuronic Acid.
They help in compressibility of cartilage and
weight bearing.
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HEPARIN Polymer of:
Glucosamine Sulphate and
Glucuronic Acid Sulphate.
o IT is produced by mast cells.
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HEPARIN IS A NATURAL ANTICOAGULANT
Heparin is a natural anticoagulant for
the blood as it prevents the
unnecessary and harmful intravascular
coagulation of blood.
Widely used as an anticoagulant drug.
Secretion and action of Heparin as an
Anticoagulant is one of Haemodynamic
mechanisms which are responsible for
the smooth blood flow.