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Biochemistry of Carbohydrates
Rajendra Dev Bhatt, PhD Scholar
Asst. Professor
Clinical Biochemistry & Laboratory Medicine
Dhulikhel Hospital-Kathmandu University Hospital
Fellow: Translational Research (2018-2022) in CVD in Nepal, NIH, USA
Carbohydrates
Carbohydrates are carbon compounds that
contain large quantities of hydroxyl groups.
The simplest carbohydrates also contain either an
aldehyde moiety (these are
termed polyhydroxyaldehydes) or a ketone
moiety (polyhydroxyketones).
All carbohydrates can be classified as
either monosaccharides, oligosaccharides or po
lysaccharides.
• Anywhere from two to ten monosaccharide units,
linked by glycosidic bonds, make up an
oligosaccharide. Polysaccharides are much larger,
containing hundreds of monosaccharide units.
• The presence of the hydroxyl groups allows
carbohydrates to interact with the aqueous
environment and to participate in hydrogen
bonding, both within and between chains.
• Derivatives of the carbohydrates can contain
nitrogens, phosphates and sulfur compounds.
Carbohydrates also can combine with lipid to
form glycolipids or with protein to
form glycoproteins.
Carbohydrates are
polyhydroxy aldehydes or
ketones, or substances that
yield such compounds on
hydrolysis.
C
C OH
H
C H
HO
C OH
H
C OH
H
CH2OH
D-glucose
O
H
Biological Importance
• Carbohydrates are chief energy source, in many
animals, they are instant source of energy. Glucose is
broken down by glycolysis/ kreb's cycle to yield ATP.
• Glucose is the source of storage of energy. It is stored
as glycogen in animals and starch in plants.
• Carbohydrates are intermediates in biosynthesis of
fats and proteins.
• Carbohydrates gets associated with lipids and
proteins to form surface antigens, receptor molecules,
vitamins and antibiotics
• They form structural and protective
components, like in cell wall of plants and
microorganisms.
• They participate in biological transport, cell-
cell communication and activation of growth
factors.
• Carbohydrates that are rich in fiber content
help to prevent constipation.
• They are crucial components of nucleic acid
(DNA & RNA) as a Ribose sugar
Monosaccharides
• The word “Monosaccharides” derived from the
Greek word “Mono” means Single and
“saccharide” means sugar
• Monosaccharides are polyhydroxy aldehydes
or ketones which cannot be further hydrolysed
to simple sugar.
• Monosaccharides are simple sugars. They are
sweet in taste. They are soluble in water. They
are crystalline in nature.
• Monosaccharides are classified in two ways. (a) First
of all, based on the number of carbon atoms present
in them and (b) secondly based on the presence of
carbonyl group.
• The naturally occurring monosaccharides contain
three to seven carbon atoms per molecule.
Monosaccharides of specific sizes may be indicated
by names composed of a stem denoting the number of
carbon atoms and the suffix -ose. For example, the
terms triose, tetrose, pentose, and hexose signify
monosaccharides with, respectively, three, four, five,
and six carbon atoms
• Monosaccharides are also classified as aldoses or
ketoses. Those monosaccharides that contain an
aldehyde functional group are called aldoses;
those containing a ketone functional group on the
second carbon atom are ketoses.
• Combining these classification systems gives
general names that indicate both the type of
carbonyl group and the number of carbon atoms
in a molecule.
Structure of Monosaccharides
1. Straight or Open Chain Structure: arranged
in a straight line. It is also called open chain
structure because the two ends remain separate
and they are not linked. Open chain structure are
of two types:
(a)Structure proposed by Fittig and Baeyer
(b)Structure proposed by Fischer known as
Fischer’s Projection Formula
2. Cyclic or Ring Structure: Haworth
(1929) proposed this formula and hence the
name Haworth’s Projection Formula. The
sugar molecules exist in two type of rings
which are as follows:
(a)Furanose Ring – 5 membered ring
(b)Pyranose Ring- 6 membered ring
Properties of Monosaccharides
1.Colour - colourless
2.Shape - crystalline
3.Solubility – water soluble
4.Taste – sweet
5.Optical activity – Optically active. (a) Dextrorotatory
(‘d’ form) and (b) Levorotatory (‘l’ form)
6. Reducing agents: Monosaccharides reduce oxidizing
agent such as hydrogen peroxide. In such reaction, sugar
is oxidized at the carbonyl group and oxidizing agent
becomes reduced.
7. Formation of Osazone
Disaccharides
• Disaccharides consist of two sugars joined by
an O-glycosidic bond. The most abundant
disaccharides are sucrose,lactose and maltose.
Other disaccharides include isomaltose,
cellobiose and trehalose.
1. Homodisaccharides
2. Heterodisaccharides
Disaccharides 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 (in this case, between
two monosaccharides) is known as a glycosidic bond.
Glycosidic bonds (also called glycosidic linkages) can
be of the alpha or the beta type.
An alpha bond is formed when the OH group on the
carbon-1 of the first glucose is below the ring plane,
and a beta bond is formed when the OH group on
the carbon-1 is above the ring plane.
Malt sugar.
Produced during the course of digestion of
starch by the enzyme amylase.
Two α-D-glucose units held together by
α(1→4) glycosidic bond.
MALTOSE
Lactose, milk sugar, is composed of galactose & glucose,
with b(14) linkage from the anomeric OH of galactose.
Lactose
O
OH
OH
CH2 OH
O
OH
OH
CH2 OH
O
OH
OH
β-D-galactose & β-D-glucose units held
together by β(1→4) glycosidic bond.
SUCROSE
Cane sugar.
α-D-glucose &β-D-fructose units held together by
(α1→β2) glycosidic bond.
Reducing groups in both are involved in bond
formation, hence non reducing.
Carbohydrate Nomenclature
• The predominant carbohydrates encountered in
the body are structurally related to the
aldotriose glyceraldehyde and to the
ketotriose dihydroxyacetone.
• All carbohydrates contain at least one
asymmetrical (chiral) carbon and are,
therefore, optically active.
STEREOISOMERS
• Compounds having same structural formula,
but differing in spatial configuration are
known as stereoisomers. While writing the
molecular formula of monosaccharides, the
spatial arrangements of H and OH groups are
important, since they contain asymmetric
carbon atoms.
• Asymmetric carbon means that four different
groups are attached to the same carbon.
The reference molecule is glyceraldehyde (glycerose)
which has a single asymmetric
carbon atom.
The number of possible stereoisomers depends on the
number of asymmetric carbon atoms by theformula 2n
where n is the number of asymmetric carbon atoms.
D and L Isomerism of Glucose
• With reference to the penultimate carbon atom (i.e.
C5 in the case of glucose), the configuration of H and
OH groups is changed and two mirror imagesare
produced.
Optical Activity
The presence of asymmetrical carbon atom causes
optical activity. When a beam of plane-polarized
light is passed through a solution of carbohydrates,
it will rotate the light either to right or to left. Please
note that the D- and L-notation has no bearing with
the optical activity. Depending on the rotation,
molecules are called dextrorotatory (+) (d) or
levorotatory (-) (l).
Thus D-glucose is dextrorotatory but D-fructose
is levorotatory.
Epimerism of Aldoses
When sugars are different from one another, only
in configuration with regard to a single carbon
atom, other than the reference carbon atom,
they are called epimers.
Anomerism of Sugars
• Anomers are cyclic monosaccharides differing
from each other in the configuration of C-1 or
C-2 carbon.
• For aldoses, it is C-1 and C-2 for ketoses.
• The alpha & beta forms of glucose are
collectively called anomers of glucose and their
interconversion is called anomerization.
• Experimental observation of anomerization can
be done by observing the mutarotation in a
solution containing the anomers.
Mutarotation
Review
1. Which monosaccharide is the primary
energy source for the human body?
a. Fructose
b. Galactose
c. Glucose
d. Ribose
c. Glucose
2. Sucrose is a disaccharide composed of
which two monosaccharides?
a. Glucose and fructose
b. Glucose and galactose
c. Glucose and ribose
d. Fructose and galactose
a. Glucose and fructose
3. In the structure of a disaccharide, the
glycosidic bond is formed between:
a. Two hydroxyl groups
b. An amino group and a carboxyl group
c. Two carbonyl groups
d. An anomeric carbon and a hydroxyl group
a. Two hydroxyl groups
POLYSACCHARIDES
• A long chain of monosaccharides linked by
glycosidic bonds is known as a polysaccharide .
• 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.
• The monomeric building blocks used to generate
polysaccharides can be varied; in all cases,
however, the predominant monosaccharide found
in polysaccharides is D-glucose.
• When polysaccharides are composed of a single
monosaccharide building block, they are
termed Homopolysaccharides or Homoglycans.
• Polysaccharides composed of more than one type
of monosaccharide are termed
Heteropolysaccharides or Heteroglycans.
Homoglycans:
Glycogen
Glycogen is the major form of stored carbohydrate
in animals.
This crucial molecule is a homopolymer of glucose
in α–(1,4) linkage; it is also highly branched, with
α–(1,6) branch linkages occurring every 8-10
residues.
Glycogen is a very compact structure that results
from the coiling of the polymer chains.
This compactness allows large amounts of carbon
energy to be stored in a small volume, with little
effect on cellular osmolarity.
Glycogen Structure. The blue balls represent glucose linked by α1,4
glycosidic bonds. The red balls represent glucose at branch points where there
are both α1,4 and α1,6 glycosidic bonds. The orange balls represent the
reducing ends of the polymeric chains of α1,4-linked glucoses.
Starch
Starch is the major form of stored carbohydrate in
plant cells. Its structure is identical to glycogen,
except for a much lower degree of branching (about
every 20–30 residues).
Unbranched starch is called amylose; branched
starch is called amylopectin.
When starch is treated with boiling water, 10-20% is
solubilized; this part is called amylose. Amylose is
made up of glucose units with alpha-1,4 glycosidic
linkages.
The insoluble part absorbs water and forms paste
like gel; this is called amylopectin. Amylopectin
is also made up of glucose units, but is highly
branched with molecular weight more than 1
million. The branching points are made by alpha-
1,6 linkage.
Starch will form a blue colored complex with
iodine; this color disappears on heating and
reappears when cooled. This is a sensitive test for
starch.
Starch is non reducing because the free sugar
groups are negligible in number.
Salivary amylase and pancreatic amylase are
alpha-amylases, which act at random on alpha-
1,4 glycosidic bonds to split starch into smaller
units (dextrins), and finally to alpha-maltose.
Beta-amylases are of plant origin (almond,
germinating seeds, etc) which split starch to form
beta-maltose. They act on amylose to split
maltose units consecutively.
Cellulose
It is the supporting tissues of plants. Cellulose constitutes
99% of cotton, 50% of wood and is the most abundant
organic material in nature.
It is made up of glucose units combined with beta-1,4
linkages. It has a straight line structure, with no branching
points.
Beta-1,4 bridges are hydrolysed by the enzyme
cellobiase. But this enzyme is absent in animal and
human digestive system, and hence cellulose cannot be
digested.
Herbivorous animals have large caecum, which harbor
bacteria. These bacteria can hydrolyse cellulose, and the
glucose produced is utilized by the animal.
Inulin
• It is a long chain homoglycan composed of D-
fructose units with beta-1,2 linkages
• It is clinically used to find renal clearance
value and glomerular filtration rate
• It is the reserve carbohydrate present in
various bulbs and tubers such as, dahlia,
dandelion, onion, garlic.
Dextrans
• These are highly branched homopolymers of glucose
units with 1-6, 1-4 and 1-3 linkages.
• They are produced by microorganisms
• It may be noted that dextrans are different from
previously described dextrins
• D-glucose is otherwise called Dextrose, a term often
used in bed-side medicine, e.g. dextrose drip.
• Dextrin is the partially digested product of starch.
• Dextran is high molecular weight carbohydrate,
synthesized by bacteria
HETEROGLYCANS:
Agar
• It is prepared from sea weeds. It contains
galactose, glucose and other sugars
• It is dissolved in water at 100°C, which upon
cooling sets into a gel. Agar cannot be digested
by bacteria and hence used widely as a
supporting agent to culture bacterial colonies.
• Agarose is made up of galactose combined
with 3,6-anhydrogalactose units; it is used as
matrix for electrophoresis
MUCOPOLYSACCHARIDES
• Mucopolysaccharides or glycosamino glycans
(GAG) are heteropolysaccharides, containing uronic
acid and amino sugars.
• Acetylated amino groups,sulfate and carboxyl groups
are also generally present. Because of the presence of
these charged groups, they attract water molecules
and so they produce viscous solutions.
• Mucopolysaccharides in combination with proteins
form mucoproteins. Examples of
mucopolysaccharides are hyaluronic acid, heparin,
chondroitin sulfate, dermatan sulfate and keratan
sulfate.
Hyaluronic Acid
It is present in connective tissues, tendons,
synovial fluid and vitreous humor. It serves as a
lubricant in joint cavities. It is composed of
repeating units of N-Acetyl-glucosamine →
beta-1, 4-Glucuronic acid → beta-1-3-N-Acetyl
glucosamine and so on.
Heparin
• It is an anticoagulant widely used when taking blood
in vitro for clinical studies. It is also used in vivo in
suspected thrombo-embolic conditions to prevent
intravascular coagulation.
• Heparin is present in liver, lungs, spleen and
monocytes. Commercial preparation of eparin is
from animal lung tissues.
• It contains repeating units of sulphated glucosamine
→ alpha-1, 4-L-iduronic acid →and so on
Chondroitin Sulphate
• It is present in ground substance of connective
tissues widely distributed in cartilage, bone,
tendons, cornea and skin. It is composed of
repeating units of glucuronic acid → beta-1,3-
N-acetyl galactosamine sulphate → beta-1, 4
and so on.
Keratan Sulphate
• It is the only GAG which does not contain
any uronic acid. The repeating units are
galactose and N-acetyl glucosamine in beta
linkage. It is found in cornea and tendons.
Dermatan Sulphate
• It contains L-iduronic acid and N-acetyl
galactosamine in beta -1, 3 linkages. It is found
in skin, blood vessels and heart valves.
GLYCOPROTEINS AND
MUCOPROTEINS
When the carbohydrate chains are attached to a
polypeptide chain it is called a proteoglycan. If
the carbohydrate content is less than 10%, it is
generally named as a glycoprotein.
If the carbohydrate content is more than 10% it
is a mucoprotein. (But some authors use these
words as synonyms).
They are seen in almost all tissues and cell
membranes
Review
1. Sara is studying nutrition and as an assignment she has
been asked to find examples of each type of carbohydrate in
the food that she consumes over the course of a week. Sarah
is eating pasta today and knows that it contains starch made
of a long chain of many sugars. What type of carbohydrate
would you classify starch as?
a. Monosaccharide
b. Disaccharide
c. Oligosaccharide
d. Polysaccharide
a. Polysaccharide
2. Which of the following is a polysaccharide
composed of glucose units linked by β-1,4-
glycosidic bonds?
A) Cellulose
B) Starch
C) Glycogen
D) Chitin
A) Cellulose
3. Glycosaminoglycans (GAGs) are a type of
polysaccharide commonly found in the
extracellular matrix. Which one of the following
is NOT a GAG?
A) Hyaluronic acid
B) Chondroitin sulfate
C) Amylose
D) Heparin
C) Amylose
THANK YOU

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Biochemistry of Carbohydrates for MBBS, BDS, Lab Med 2024.pptx

  • 1. Biochemistry of Carbohydrates Rajendra Dev Bhatt, PhD Scholar Asst. Professor Clinical Biochemistry & Laboratory Medicine Dhulikhel Hospital-Kathmandu University Hospital Fellow: Translational Research (2018-2022) in CVD in Nepal, NIH, USA
  • 2. Carbohydrates Carbohydrates are carbon compounds that contain large quantities of hydroxyl groups. The simplest carbohydrates also contain either an aldehyde moiety (these are termed polyhydroxyaldehydes) or a ketone moiety (polyhydroxyketones). All carbohydrates can be classified as either monosaccharides, oligosaccharides or po lysaccharides.
  • 3. • Anywhere from two to ten monosaccharide units, linked by glycosidic bonds, make up an oligosaccharide. Polysaccharides are much larger, containing hundreds of monosaccharide units. • The presence of the hydroxyl groups allows carbohydrates to interact with the aqueous environment and to participate in hydrogen bonding, both within and between chains. • Derivatives of the carbohydrates can contain nitrogens, phosphates and sulfur compounds. Carbohydrates also can combine with lipid to form glycolipids or with protein to form glycoproteins.
  • 4. Carbohydrates are polyhydroxy aldehydes or ketones, or substances that yield such compounds on hydrolysis. C C OH H C H HO C OH H C OH H CH2OH D-glucose O H
  • 5. Biological Importance • Carbohydrates are chief energy source, in many animals, they are instant source of energy. Glucose is broken down by glycolysis/ kreb's cycle to yield ATP. • Glucose is the source of storage of energy. It is stored as glycogen in animals and starch in plants. • Carbohydrates are intermediates in biosynthesis of fats and proteins. • Carbohydrates gets associated with lipids and proteins to form surface antigens, receptor molecules, vitamins and antibiotics
  • 6. • They form structural and protective components, like in cell wall of plants and microorganisms. • They participate in biological transport, cell- cell communication and activation of growth factors. • Carbohydrates that are rich in fiber content help to prevent constipation. • They are crucial components of nucleic acid (DNA & RNA) as a Ribose sugar
  • 7. Monosaccharides • The word “Monosaccharides” derived from the Greek word “Mono” means Single and “saccharide” means sugar • Monosaccharides are polyhydroxy aldehydes or ketones which cannot be further hydrolysed to simple sugar. • Monosaccharides are simple sugars. They are sweet in taste. They are soluble in water. They are crystalline in nature.
  • 8. • Monosaccharides are classified in two ways. (a) First of all, based on the number of carbon atoms present in them and (b) secondly based on the presence of carbonyl group. • The naturally occurring monosaccharides contain three to seven carbon atoms per molecule. Monosaccharides of specific sizes may be indicated by names composed of a stem denoting the number of carbon atoms and the suffix -ose. For example, the terms triose, tetrose, pentose, and hexose signify monosaccharides with, respectively, three, four, five, and six carbon atoms
  • 9. • Monosaccharides are also classified as aldoses or ketoses. Those monosaccharides that contain an aldehyde functional group are called aldoses; those containing a ketone functional group on the second carbon atom are ketoses. • Combining these classification systems gives general names that indicate both the type of carbonyl group and the number of carbon atoms in a molecule.
  • 10.
  • 11. Structure of Monosaccharides 1. Straight or Open Chain Structure: arranged in a straight line. It is also called open chain structure because the two ends remain separate and they are not linked. Open chain structure are of two types: (a)Structure proposed by Fittig and Baeyer (b)Structure proposed by Fischer known as Fischer’s Projection Formula
  • 12.
  • 13. 2. Cyclic or Ring Structure: Haworth (1929) proposed this formula and hence the name Haworth’s Projection Formula. The sugar molecules exist in two type of rings which are as follows: (a)Furanose Ring – 5 membered ring (b)Pyranose Ring- 6 membered ring
  • 14. Properties of Monosaccharides 1.Colour - colourless 2.Shape - crystalline 3.Solubility – water soluble 4.Taste – sweet 5.Optical activity – Optically active. (a) Dextrorotatory (‘d’ form) and (b) Levorotatory (‘l’ form) 6. Reducing agents: Monosaccharides reduce oxidizing agent such as hydrogen peroxide. In such reaction, sugar is oxidized at the carbonyl group and oxidizing agent becomes reduced. 7. Formation of Osazone
  • 15. Disaccharides • Disaccharides consist of two sugars joined by an O-glycosidic bond. The most abundant disaccharides are sucrose,lactose and maltose. Other disaccharides include isomaltose, cellobiose and trehalose. 1. Homodisaccharides 2. Heterodisaccharides
  • 16. Disaccharides 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 (in this case, between two monosaccharides) is known as a glycosidic bond. Glycosidic bonds (also called glycosidic linkages) can be of the alpha or the beta type.
  • 17. An alpha bond is formed when the OH group on the carbon-1 of the first glucose is below the ring plane, and a beta bond is formed when the OH group on the carbon-1 is above the ring plane.
  • 18.
  • 19. Malt sugar. Produced during the course of digestion of starch by the enzyme amylase. Two α-D-glucose units held together by α(1→4) glycosidic bond. MALTOSE
  • 20. Lactose, milk sugar, is composed of galactose & glucose, with b(14) linkage from the anomeric OH of galactose. Lactose O OH OH CH2 OH O OH OH CH2 OH O OH OH β-D-galactose & β-D-glucose units held together by β(1→4) glycosidic bond.
  • 21. SUCROSE Cane sugar. α-D-glucose &β-D-fructose units held together by (α1→β2) glycosidic bond. Reducing groups in both are involved in bond formation, hence non reducing.
  • 22.
  • 23.
  • 24. Carbohydrate Nomenclature • The predominant carbohydrates encountered in the body are structurally related to the aldotriose glyceraldehyde and to the ketotriose dihydroxyacetone. • All carbohydrates contain at least one asymmetrical (chiral) carbon and are, therefore, optically active.
  • 25. STEREOISOMERS • Compounds having same structural formula, but differing in spatial configuration are known as stereoisomers. While writing the molecular formula of monosaccharides, the spatial arrangements of H and OH groups are important, since they contain asymmetric carbon atoms. • Asymmetric carbon means that four different groups are attached to the same carbon.
  • 26. The reference molecule is glyceraldehyde (glycerose) which has a single asymmetric carbon atom. The number of possible stereoisomers depends on the number of asymmetric carbon atoms by theformula 2n where n is the number of asymmetric carbon atoms.
  • 27. D and L Isomerism of Glucose • With reference to the penultimate carbon atom (i.e. C5 in the case of glucose), the configuration of H and OH groups is changed and two mirror imagesare produced.
  • 28. Optical Activity The presence of asymmetrical carbon atom causes optical activity. When a beam of plane-polarized light is passed through a solution of carbohydrates, it will rotate the light either to right or to left. Please note that the D- and L-notation has no bearing with the optical activity. Depending on the rotation, molecules are called dextrorotatory (+) (d) or levorotatory (-) (l). Thus D-glucose is dextrorotatory but D-fructose is levorotatory.
  • 29. Epimerism of Aldoses When sugars are different from one another, only in configuration with regard to a single carbon atom, other than the reference carbon atom, they are called epimers.
  • 30. Anomerism of Sugars • Anomers are cyclic monosaccharides differing from each other in the configuration of C-1 or C-2 carbon. • For aldoses, it is C-1 and C-2 for ketoses.
  • 31. • The alpha & beta forms of glucose are collectively called anomers of glucose and their interconversion is called anomerization. • Experimental observation of anomerization can be done by observing the mutarotation in a solution containing the anomers.
  • 33.
  • 34.
  • 35.
  • 36. Review 1. Which monosaccharide is the primary energy source for the human body? a. Fructose b. Galactose c. Glucose d. Ribose c. Glucose
  • 37. 2. Sucrose is a disaccharide composed of which two monosaccharides? a. Glucose and fructose b. Glucose and galactose c. Glucose and ribose d. Fructose and galactose a. Glucose and fructose
  • 38. 3. In the structure of a disaccharide, the glycosidic bond is formed between: a. Two hydroxyl groups b. An amino group and a carboxyl group c. Two carbonyl groups d. An anomeric carbon and a hydroxyl group a. Two hydroxyl groups
  • 39. POLYSACCHARIDES • A long chain of monosaccharides linked by glycosidic bonds is known as a polysaccharide . • 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.
  • 40. • The monomeric building blocks used to generate polysaccharides can be varied; in all cases, however, the predominant monosaccharide found in polysaccharides is D-glucose. • When polysaccharides are composed of a single monosaccharide building block, they are termed Homopolysaccharides or Homoglycans. • Polysaccharides composed of more than one type of monosaccharide are termed Heteropolysaccharides or Heteroglycans.
  • 41. Homoglycans: Glycogen Glycogen is the major form of stored carbohydrate in animals. This crucial molecule is a homopolymer of glucose in α–(1,4) linkage; it is also highly branched, with α–(1,6) branch linkages occurring every 8-10 residues. Glycogen is a very compact structure that results from the coiling of the polymer chains. This compactness allows large amounts of carbon energy to be stored in a small volume, with little effect on cellular osmolarity.
  • 42. Glycogen Structure. The blue balls represent glucose linked by α1,4 glycosidic bonds. The red balls represent glucose at branch points where there are both α1,4 and α1,6 glycosidic bonds. The orange balls represent the reducing ends of the polymeric chains of α1,4-linked glucoses.
  • 43. Starch Starch is the major form of stored carbohydrate in plant cells. Its structure is identical to glycogen, except for a much lower degree of branching (about every 20–30 residues). Unbranched starch is called amylose; branched starch is called amylopectin. When starch is treated with boiling water, 10-20% is solubilized; this part is called amylose. Amylose is made up of glucose units with alpha-1,4 glycosidic linkages.
  • 44. The insoluble part absorbs water and forms paste like gel; this is called amylopectin. Amylopectin is also made up of glucose units, but is highly branched with molecular weight more than 1 million. The branching points are made by alpha- 1,6 linkage. Starch will form a blue colored complex with iodine; this color disappears on heating and reappears when cooled. This is a sensitive test for starch. Starch is non reducing because the free sugar groups are negligible in number.
  • 45. Salivary amylase and pancreatic amylase are alpha-amylases, which act at random on alpha- 1,4 glycosidic bonds to split starch into smaller units (dextrins), and finally to alpha-maltose. Beta-amylases are of plant origin (almond, germinating seeds, etc) which split starch to form beta-maltose. They act on amylose to split maltose units consecutively.
  • 46. Cellulose It is the supporting tissues of plants. Cellulose constitutes 99% of cotton, 50% of wood and is the most abundant organic material in nature. It is made up of glucose units combined with beta-1,4 linkages. It has a straight line structure, with no branching points. Beta-1,4 bridges are hydrolysed by the enzyme cellobiase. But this enzyme is absent in animal and human digestive system, and hence cellulose cannot be digested. Herbivorous animals have large caecum, which harbor bacteria. These bacteria can hydrolyse cellulose, and the glucose produced is utilized by the animal.
  • 47. Inulin • It is a long chain homoglycan composed of D- fructose units with beta-1,2 linkages • It is clinically used to find renal clearance value and glomerular filtration rate • It is the reserve carbohydrate present in various bulbs and tubers such as, dahlia, dandelion, onion, garlic.
  • 48. Dextrans • These are highly branched homopolymers of glucose units with 1-6, 1-4 and 1-3 linkages. • They are produced by microorganisms • It may be noted that dextrans are different from previously described dextrins • D-glucose is otherwise called Dextrose, a term often used in bed-side medicine, e.g. dextrose drip. • Dextrin is the partially digested product of starch. • Dextran is high molecular weight carbohydrate, synthesized by bacteria
  • 49. HETEROGLYCANS: Agar • It is prepared from sea weeds. It contains galactose, glucose and other sugars • It is dissolved in water at 100°C, which upon cooling sets into a gel. Agar cannot be digested by bacteria and hence used widely as a supporting agent to culture bacterial colonies. • Agarose is made up of galactose combined with 3,6-anhydrogalactose units; it is used as matrix for electrophoresis
  • 50. MUCOPOLYSACCHARIDES • Mucopolysaccharides or glycosamino glycans (GAG) are heteropolysaccharides, containing uronic acid and amino sugars. • Acetylated amino groups,sulfate and carboxyl groups are also generally present. Because of the presence of these charged groups, they attract water molecules and so they produce viscous solutions. • Mucopolysaccharides in combination with proteins form mucoproteins. Examples of mucopolysaccharides are hyaluronic acid, heparin, chondroitin sulfate, dermatan sulfate and keratan sulfate.
  • 51. Hyaluronic Acid It is present in connective tissues, tendons, synovial fluid and vitreous humor. It serves as a lubricant in joint cavities. It is composed of repeating units of N-Acetyl-glucosamine → beta-1, 4-Glucuronic acid → beta-1-3-N-Acetyl glucosamine and so on.
  • 52. Heparin • It is an anticoagulant widely used when taking blood in vitro for clinical studies. It is also used in vivo in suspected thrombo-embolic conditions to prevent intravascular coagulation. • Heparin is present in liver, lungs, spleen and monocytes. Commercial preparation of eparin is from animal lung tissues. • It contains repeating units of sulphated glucosamine → alpha-1, 4-L-iduronic acid →and so on
  • 53. Chondroitin Sulphate • It is present in ground substance of connective tissues widely distributed in cartilage, bone, tendons, cornea and skin. It is composed of repeating units of glucuronic acid → beta-1,3- N-acetyl galactosamine sulphate → beta-1, 4 and so on.
  • 54. Keratan Sulphate • It is the only GAG which does not contain any uronic acid. The repeating units are galactose and N-acetyl glucosamine in beta linkage. It is found in cornea and tendons.
  • 55. Dermatan Sulphate • It contains L-iduronic acid and N-acetyl galactosamine in beta -1, 3 linkages. It is found in skin, blood vessels and heart valves.
  • 56. GLYCOPROTEINS AND MUCOPROTEINS When the carbohydrate chains are attached to a polypeptide chain it is called a proteoglycan. If the carbohydrate content is less than 10%, it is generally named as a glycoprotein. If the carbohydrate content is more than 10% it is a mucoprotein. (But some authors use these words as synonyms). They are seen in almost all tissues and cell membranes
  • 57. Review 1. Sara is studying nutrition and as an assignment she has been asked to find examples of each type of carbohydrate in the food that she consumes over the course of a week. Sarah is eating pasta today and knows that it contains starch made of a long chain of many sugars. What type of carbohydrate would you classify starch as? a. Monosaccharide b. Disaccharide c. Oligosaccharide d. Polysaccharide a. Polysaccharide
  • 58. 2. Which of the following is a polysaccharide composed of glucose units linked by β-1,4- glycosidic bonds? A) Cellulose B) Starch C) Glycogen D) Chitin A) Cellulose
  • 59. 3. Glycosaminoglycans (GAGs) are a type of polysaccharide commonly found in the extracellular matrix. Which one of the following is NOT a GAG? A) Hyaluronic acid B) Chondroitin sulfate C) Amylose D) Heparin C) Amylose

Editor's Notes

  1. Glucose