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Carbohydrate chemistry
Dr. Herat D. Soni
Assistant professor
Rural medical college
Loni
Definition
Carbohydrates may be defined as
polyhydroxy aldehydes or
ketones or compounds which
produce them on hydrolysis.
Formula = (C.H2O)n
Biomedical Importance
 Most abundant dietary source of energy. Brain cells
and RBCs are almost wholly dependent on
carbohydrates as the energy source.
 Also serve as storage form of energy –Glycogen.
 Carbohydrates are precursors for many organic
compounds (fats, amino acids).
 Participate in the structure of cell membrane &
cellular functions (cell growth, adhesion and
fertilization).
 Certain carbohydrate derivatives are used as
drugs, like cardiac glycosides / antibiotics.
 DM (diabetes mellitus)
Sources
CLASSIFICATION OF
CARBOHYDRATE
Classification
1
• Monosaccharide
2
• Oligosaccharide
3
• Polysaccharide
Monosaccharide
Cannot further Hydrolyzed
Oligosaccharide
• Oligosaccharides(Greek: oligo-few) contain 2-1O
monosaccharide molecules
• Joined by glycosidic bond
Polysaccharides
 Contain more than 10 monosaccharide
units.
Polysaccharides
Homopolysaccharides
Starch
Glycogen
Cellulose
Inulin
Dextrans
Chitin
Heteropolysacchrides
Agar
Mucopolysaccharide
Isomers
 Same chemical formula but different
structural formula
 Example = Glucose and fructose
C6H12O6
Stereoisomer
 Same chemical and structural formula but
differ in spatial configuration.
Asymmetric carbon atom
 Asymmetric carbon means that four
different groups are attached to the same
carbon.
 The reference molecule is glyceraldehyde
which has a single asymmetric carbon
atom.
 The number of possible stereoisomer
depends on the number of asymmetric
carbon atoms by the formula 2
n
where n is
the number of asymmetric carbon atoms.
Reference Carbon Atom of
Sugars
All monosaccharide can be considered as molecules
derived from glyceraldehyde by successive addition of
carbon atoms. Therefore, penultimate carbon atom is the
reference carbon atom for naming the mirror images
D and L isomerism(Enantiomers)
• D-sugars are naturally occurring sugars and
body can metabolize only D-sugars.
• D-glucose is dextrorotatory. In clinical practice,
it is often called as dextrose
Optical isomerism(d and l)
 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.
 Right = dextrorotatory (+) (d)
 Left = levorotatory (-) (l)
 D-glucose is dextrorotatory but D-fructose
is levorotatory
 Equimolecular mixture of optical isomers
has no net rotation (racemic mixture)
Epimers
 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.
Epimers
Anomers
To understand this we first understand
Three Representations of Glucose
Structure
open chain
projection
formula
Fischer's
formula
Haworth’s
formula
 The 1st carbon, aldehyde group is
condensed with the hydroxyl group of the
5th carbon to form a ring. Ring structure
represents hemi acetal form.
 Glucose exists in biological systems not
as a rectangle, but as a pyranose ring.
 b-D-glucopyranose is the predominant
form (63%).
 D-glucose has two anomers, alpha and
beta varieties.
 These anomers are produced by the
spatial configuration with reference to the
first carbon atom in aldoses and second
carbon atom in ketoses.
 These carbon atoms are known as
anomeric carbon atoms.
Fischer's formula
Haworth formula
Anomeric carbon atom
Mutarotation
 When D glucose is crystallized at
room temperature, and a fresh
solution is prepared, its specific
rotation of polarized light is +112o
;
but after 12–18 hours it changes
to +52.5o
.
 This change in rotation with time
is called mutarotation.
ɑ-D-glucopyranose
Rotation of 112
O
ɓ-D-glucopyranose
Rotation of 19
0
1/3 are alpha type and 2/3rd are beta
variety to get the specific rotation of +52.5o
Mutarotation
DISACCHARIDES
Sucrose
Maltose
Isomaltose
Lactose.
Sucrose
• It is the sweetening agent known as cane
sugar.
• It is present in sugarcane and various fruits.
 Hydrolysis of sucrose (optical rotation
+66.5°) will produce one molecule of
glucose (+52.5°) and one molecule of
fructose (–92°).
 Therefore, the products will change the
dextrorotation to levorotation, or the plane
of rotation is inverted.
 Equimolecular mixture of glucose and
fructose thus formed is called invert sugar.
 The enzyme producing hydrolysis of sucrose
is called sucrase or invertase.
 Honey contains invert sugar.
 Invert sugar is sweeter than sucrose.
Lactose
It is the sugar present in milk
Lactose intolerance
Maltose
Isomaltose
REACTIONS OF
CARBOHYDRATE
Benedict’s test
Principle
 The principle of Benedict's test is that
when reducing sugars are heated in the
presence of an alkali(pH 10.6), they get
converted to powerful reducing
compounds known as enediols.
 Enediols reduce the cupric ions (Cu2+)
present in the Benedict's reagent to
cuprous ions (Cu+) which get precipitated
as insoluble red copper oxide.
 Detect the presence of glucose in urine
(glucosuria).
 It is a standard laboratory test employed
for follow-up of diabetes mellitus in PHC.
 Benedict's reagent contains sodium
carbonate, copper sulfate and sodium
citrate
 Any sugar with free aldehyde/keto group
will reduce the Benedict's reagent.
Therefore, this is not specific for glucose.
Carbohydrates giving positive
Benedict ’ s test:
 Glucose, Fructose, Galactose
 Lactose, Maltose
 Sucrose ???????
 Starches do not react or react very poorly
with Benedict's reagent, due to the
relatively small number of reducing sugar
moieties, which occur only at the ends of
carbohydrate chains.
Non-Carbohydrates giving
positive Benedict ’ s test
 High concentration of Uric acid and
Ketones
 Homogentisic acid (solution turns black
due to black colored oxidized
homogentisic acid)
 Vitamin C (even without Boiling)
 Certain drugs like aspirin, cephalosporins
Glucose oxidase test
 Glucose + O2
Gluconolactone + H2O2
 H2O2 + (reduced colourless dye)
(Oxidized colored dye)
Glucose Oxidase
Peroxidase
 Reagents for this test are present on a strip
of paper in solid form.
 When the paper is wet with urine, the
reagents dissolve in urine on paper and
react with glucose in urine.
 The darkness of color can be correlated
with amount of glucose present in urine.
 Because Glucose oxidase enzyme can act
only on beta-D Glucose, other reducing
substances do not give this test positive.
 Thus, compounds like Vitamin C,
Aspirin utilize H2O2 produced in the
reaction.
 Due to lack of H2O2, Peroxidase can
not oxidize dye. Thus, glucose may
not be detected even if present, if
urine contain Vitamin C or Aspirin in
large amount. This phenomenon is
called false negative result.
Osazone Formation
 All reducing sugars will form
osazones with excess of phenyl
hydrazine when kept at boiling
temperature.
 Glucose, Galactose and Fructose will
produce the same needle-shaped
crystals. Why?
Molisch’s test
 All carbohydrates when treated with conc.
sulphuric acid undergo dehydration to
give fufural compounds. These
compounds condense with Alpha-napthol
to form colored compounds.
 Molish test is given by sugars with at
least five carbons because it involves
furfural derivatives, which are five carbon
compounds.
Purple ring at junction
Fehling’s test
Same principle as benedicts test
Fehling’s A contains 7% copper
sulphate and Fehling’s B contains
sodium potassium tartarate.
Barfoed’s test
 This test is based on the same principle as
Benedict’s test.
 But, the test medium is acidic.
 In acidic medium (pH 4.6)
monosaccharides react faster than
disaccharide.
 Barfoed’s reagent contains copper acetate
in glacial acetic acid.
Scanty Red precipitate at
bottom of tube
Seliwanoff’s test
 Seliwanoff’s test is a chemical test
which distinguishes between aldose
and ketose sugars.
 Ketohexoses like fructose on
treatment with HCl form 5-
hydroxymethylfurfural, which on
condensation with resorcinol gives a
cherry red complex.
Cherry
red color
Oxidation
The glucuronic acid is used by the body for
conjugation with insoluble molecules to make them
soluble in water for detoxification purpose and also
for synthesis of heteropolysaccharides.
Reduction to Form Alcohols
 When treated with reducing agents
hydrogen can reduce sugars. Aldose yields
corresponding alcohol.
 Glucose is reduced to sorbitol
 mannose to mannitol
 fructose becomes sorbitol and mannitol
 Galactose is reduced to dulcitol and
 ribose to ribitol.
Significance of reduction
 Sorbitol, mannitol and dulcitol are
used to identify bacterial colonies.
 Mannitol is also used to reduce
intracranial tension by forced
diuresis.
 The osmotic effect of sorbitol produces
changes in tissues when they
accumulate in abnormal amounts, e.g.
cataract of lens.
Cataract
Retinopathy
Nephropathy
Neuropathy
Lactulose
• Lactulose is also known as beta-D-
galactopyranosyl-D-fructofuranose.
• Used in constipation
Glycosides
 The hydroxyl group of anomeric carbon of a
carbohydrate can join with a hydroxyl group
of another carbohydrate or some other
compound to form a glycoside and the bond
so formed is known as glycosidic bond.
 eg. R-OH + HO-R’ R-O-R' + H2O
 The non-carbohydrate moiety is known as
aglycone –phenol, sterol, glycerol and
methanol.
 Glycosidic bond can be N-linked or, O-
linked.
Biomedical importance of
glycosides
 Cardiac Glycosides –Digoxin, Digitoxin
◦ Used in cardiac insufficiency.
◦ Stimulate cardiac muscle contraction.
◦ Contain steroids as aglycone
component.
 Ouabain –Sodium pump inhibitor.
 Streptomycin
◦ Antibiotic
◦ Given in Tuberculosis
 Phloridzin
◦ cause renal damage, glycosuria.
◦ Blocks the transport of sugar across the
mucosal cells of small intestine & also
renal tubular epithelium.
Formation of Esters
 Esterification of alcoholic groups of
monosaccharides with phosphoric
acid is a common reaction in
metabolism.
 Examples :Glucose-6-phosphate, and
Glucose-1-phosphate.
 ATP donates the phosphate moiety.
Amino sugars
Amino groups may be substituted for hydroxyl
groups of sugars to give rise to amino sugars
Importance
Amino sugars Found in
Glucosamine Hyaluronic acid, heparin and
blood group substances
Galactosamine Chondroitin sulphate of
cartilage, bone and tendons.
Mannosamine constituent of glycoproteins
N-acetylglucosamine
(GluNac) and N-
acetyl galactosamine
(GalNac)
constituents of
glycoproteins,
Mucopolysaccharide and cell
membrane antigens.
Deoxy Sugars
Oxygen of the hydroxyl group may be removed to
form Deoxy sugars
• 2-deoxy D-ribose is important
part in DNA.
Homopolysaccharides
Starch
Glycogen
Cellulose
Inulin
Dextrans
Chitin
Starch
 It is the reserve carbohydrate of plant
kingdom
 Sources: Potatoes, cereals (rice,
wheat) and other food grains.
 Starch is composed of amylose and
amylopectin.
 Amylose is made up of glucose units
with alpha-1,4 glycosidic linkages to
form an unbranched long chain. Water
soluble.
 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.
The branching points are made by
alpha-1,6 linkage
Iodine test for starch
 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 nonreducing because the
free sugar groups are negligible in
number.
Hydrolysis of starch
 Amylodextrin = violet color with
iodine and is non-reducing.
 Erythrodextrin = red color with
iodine and mildly reduce the
Benedict's solution.
 Achrodextrins = no color with
iodine, reducing)
 Maltose = (no color with iodine, but
powerfully reducing)
Short
time to
long time
Glycogen
 It is the reserve carbohydrate in animals.
It is stored in liver and muscle.
 Liver glycogen stores increase during the
well-fed state , and are depleted during a
fast.
 Glycogen is composed of glucose units
joined by alpha-1,4 links in straight
chains. It also has alpha-1,6 glycosidic
linkages at the branching points.
 Glycogen is more branched and more
compact than amylopectin.
Liver and muscle glycogen
Cellulose
 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 hydrolyzed by the
enzyme cellobiase. But this enzyme is
absent in animal and human digestive
system, and hence cellulose cannot be
digested.
Importance
Fiber can absorb 10–15 times its own
weight in water, drawing fluid into
the lumen of the intestine
Increasing bowel motility
1.Decrease the risk for constipation
It is a major constituent of fiber, the
nondigestable carbohydrate.
Intestine
Bile salt Fibers
Excreted
Cholesterol
Decreases
serum
cholesterol
level
.
2. Lower LDL cholesterol levels
Delays gastric emptying and can result in a
sensation of fullness
4. Reduced peaks of blood glucose
following a meal
Can bind various toxic substances
including carcinogens & eliminate them in
faecal matter
3.Decreases chances of some cancers
Inulin
 It is a long chain homoglycan composed
of D-fructose units with repeating beta-1,2
linkages.
 It is the reserve carbohydrate present in
various bulbs and tubers, such as onion,
garlic.
 It is clinically used to find renal
clearance value and glomerular
filtration rate.
Dextrans
 These are highly branched homopolymers
of glucose units with 1-6, 1-4 and 1-3
linkages. They are produced by micro-
organisms.
 Since they will not easily go out of
vascular compartment, they are used for
intravenous infusion as plasma volume
expander for treatment of hypovolemic
shock.
Dextrose, Dextrin and Dextran
are different
 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.
Chitin
 It is present in exoskeletons of
insects.
 It is composed of units of N-
acetylglucosamine with beta-1,4
glycosidic linkages.
Heteropolysaccharides
• Agar
• Mucopolysaccharide
Agar
 Agar = The linear polysaccharide Agarose
+ agaropectin
 It is dissolved in water at 100ºC, which
upon cooling sets into a gel. Agarose is
used as matrix for electrophoresis.
 Agar cannot be digested by bacteria and
hence used widely as a supporting agent to
culture bacterial colonies.
Mucopolysaccharide
i.e. glycosaminoglycans(GAGs)
 [acidic sugar–amino sugar]n.
 Because of their large number of negative
charges, these heteropolysaccharide chains
tend to be extended in solution. They repel
each other, and are surrounded by a shell
of water molecules. When brought
together, they “slip” past each other.
 This produces the “slippery” consistency
of mucous secretions and synovial fluid.
This property contributes to
the resilience of synovial fluid
and the vitreous humor of the
eye
GAGs Composition Tissue distribution Functions
Hyaluronic
acid
D-glucuronic acid
and N-acetyl D-
glucosamine
Connective tissue
Synovial fluid
Vitreous humor
Gel around ovum
lubricant and shock
absorbant in joints
Chondroitin
sulphate
D-glucuronic acid and N-
acetyl D-galactosamine
4-sulfate.
bone, cartilage,
Tendons,heart
valves and skin.
Helps to maintain
the structure And
shapes of tissues
Dermatan
sulfate
D-Iduronic acid and
N-acetyl D-galactosamine
4 –sulfate.
Skin Helps to maintain
shapes of tissues
Keratan
sulphate
galactose and N-acetyl
glucosamine
cornea
tendons
Keeps cornea
Transparent
Heparin sulphated glucosamine
and glucuronic acid or
iduronic acid
blood, lung, liver
,kidney, spleen
Anticoagulant
Clearing factor
Hyaluronic acid
N-Acetyl-glucosamine → beta-1, 4-
Glucuronic acid → beta-1-3-N-Acetyl
glucosamine and so on.
Hyaluronidase
Breaks b(1-4 linkages) in hyaluronic acid.
Present in high concentration in testes,
seminal fluid, and in certain snake and insect
venoms.
Hyaluronidase of semen clears the gel
(hyaluronic acid) around the ovum allowing a
better penetration of sperm into the ovum.
Serves important role in fertilization
Hyaluronidase of bacteria helps their invasion
into the animal tissues.
Chondroitin sulphate
glucuronic acid → beta-1,3-N-acetyl
galactosamine sulfate → beta-1, 4
and so on
Dermatan sulfateDermatan sulfate
L-iduronic acid and N-acetylgalactosamine
in beta-1, 3 linkages
Keratan sulphate
 Only GAG not having Uronic acid.
Heparin
It contains repeating units of sulphated
glucosamine → alpha-1, 4-L-iduronic acid
or glucuronic acid → and so on
 Heparin is an anticoagulant( prevents
blood clotting).
 Heparin helps in the release of the enzyme
lipoprotein lipase which helps in clearing
the turbidity of lipemic plasma.
 Lipoprotein lipase breaks TG in glycerol
and FFA.
HSEN
Heparan
sulphate
Capillary
On capillary
endothelial
wall surface
Lipoprotein
lipase
Heparin displaces
lipoprotein lipase from
heparan sulphate binding
site hence clearing factor
Proteoglycans and
Glycoproteins
 Proteoglycans: When carbohydrate
chains are attached to a polypeptide chain.
 Glycoproteins: Carbohydrate content ≤
10%.
Proteoglycans
Figure showing Proteoglycans aggregate
Glycoprotein Major function
Glycophorin glycoprotein of
erythrocytes cell
membrane
Collagen Structure of cartilage
and bone
Ceruloplasmin Transport protein
Immunoglobulin Defense against
infection
Intrinsic factor Absorption of vitamin
B12
Fibrinogen Blood clotting
Thank
you
Any questions?

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Chemistry of carbohydrate for M.B.B.S students

  • 1. Carbohydrate chemistry Dr. Herat D. Soni Assistant professor Rural medical college Loni
  • 2. Definition Carbohydrates may be defined as polyhydroxy aldehydes or ketones or compounds which produce them on hydrolysis. Formula = (C.H2O)n
  • 3.
  • 4.
  • 5.
  • 6. Biomedical Importance  Most abundant dietary source of energy. Brain cells and RBCs are almost wholly dependent on carbohydrates as the energy source.  Also serve as storage form of energy –Glycogen.  Carbohydrates are precursors for many organic compounds (fats, amino acids).  Participate in the structure of cell membrane & cellular functions (cell growth, adhesion and fertilization).  Certain carbohydrate derivatives are used as drugs, like cardiac glycosides / antibiotics.  DM (diabetes mellitus)
  • 11.
  • 12.
  • 13. Oligosaccharide • Oligosaccharides(Greek: oligo-few) contain 2-1O monosaccharide molecules • Joined by glycosidic bond
  • 14. Polysaccharides  Contain more than 10 monosaccharide units.
  • 16. Isomers  Same chemical formula but different structural formula  Example = Glucose and fructose C6H12O6
  • 17.
  • 18. Stereoisomer  Same chemical and structural formula but differ in spatial configuration.
  • 19.
  • 20. Asymmetric carbon atom  Asymmetric carbon means that four different groups are attached to the same carbon.  The reference molecule is glyceraldehyde which has a single asymmetric carbon atom.  The number of possible stereoisomer depends on the number of asymmetric carbon atoms by the formula 2 n where n is the number of asymmetric carbon atoms.
  • 21. Reference Carbon Atom of Sugars All monosaccharide can be considered as molecules derived from glyceraldehyde by successive addition of carbon atoms. Therefore, penultimate carbon atom is the reference carbon atom for naming the mirror images
  • 22. D and L isomerism(Enantiomers) • D-sugars are naturally occurring sugars and body can metabolize only D-sugars. • D-glucose is dextrorotatory. In clinical practice, it is often called as dextrose
  • 23. Optical isomerism(d and l)  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.  Right = dextrorotatory (+) (d)  Left = levorotatory (-) (l)  D-glucose is dextrorotatory but D-fructose is levorotatory  Equimolecular mixture of optical isomers has no net rotation (racemic mixture)
  • 24. Epimers  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.
  • 26. Anomers To understand this we first understand Three Representations of Glucose Structure
  • 28.
  • 29.  The 1st carbon, aldehyde group is condensed with the hydroxyl group of the 5th carbon to form a ring. Ring structure represents hemi acetal form.  Glucose exists in biological systems not as a rectangle, but as a pyranose ring.  b-D-glucopyranose is the predominant form (63%).
  • 30.  D-glucose has two anomers, alpha and beta varieties.  These anomers are produced by the spatial configuration with reference to the first carbon atom in aldoses and second carbon atom in ketoses.  These carbon atoms are known as anomeric carbon atoms.
  • 33. Mutarotation  When D glucose is crystallized at room temperature, and a fresh solution is prepared, its specific rotation of polarized light is +112o ; but after 12–18 hours it changes to +52.5o .  This change in rotation with time is called mutarotation.
  • 34. ɑ-D-glucopyranose Rotation of 112 O ɓ-D-glucopyranose Rotation of 19 0 1/3 are alpha type and 2/3rd are beta variety to get the specific rotation of +52.5o Mutarotation
  • 35.
  • 37. Sucrose • It is the sweetening agent known as cane sugar. • It is present in sugarcane and various fruits.
  • 38.  Hydrolysis of sucrose (optical rotation +66.5°) will produce one molecule of glucose (+52.5°) and one molecule of fructose (–92°).  Therefore, the products will change the dextrorotation to levorotation, or the plane of rotation is inverted.  Equimolecular mixture of glucose and fructose thus formed is called invert sugar.  The enzyme producing hydrolysis of sucrose is called sucrase or invertase.  Honey contains invert sugar.  Invert sugar is sweeter than sucrose.
  • 39. Lactose It is the sugar present in milk
  • 40.
  • 46. Principle  The principle of Benedict's test is that when reducing sugars are heated in the presence of an alkali(pH 10.6), they get converted to powerful reducing compounds known as enediols.  Enediols reduce the cupric ions (Cu2+) present in the Benedict's reagent to cuprous ions (Cu+) which get precipitated as insoluble red copper oxide.
  • 47.
  • 48.  Detect the presence of glucose in urine (glucosuria).  It is a standard laboratory test employed for follow-up of diabetes mellitus in PHC.  Benedict's reagent contains sodium carbonate, copper sulfate and sodium citrate  Any sugar with free aldehyde/keto group will reduce the Benedict's reagent. Therefore, this is not specific for glucose.
  • 49. Carbohydrates giving positive Benedict ’ s test:  Glucose, Fructose, Galactose  Lactose, Maltose  Sucrose ???????  Starches do not react or react very poorly with Benedict's reagent, due to the relatively small number of reducing sugar moieties, which occur only at the ends of carbohydrate chains.
  • 50. Non-Carbohydrates giving positive Benedict ’ s test  High concentration of Uric acid and Ketones  Homogentisic acid (solution turns black due to black colored oxidized homogentisic acid)  Vitamin C (even without Boiling)  Certain drugs like aspirin, cephalosporins
  • 51.
  • 52. Glucose oxidase test  Glucose + O2 Gluconolactone + H2O2  H2O2 + (reduced colourless dye) (Oxidized colored dye) Glucose Oxidase Peroxidase
  • 53.  Reagents for this test are present on a strip of paper in solid form.  When the paper is wet with urine, the reagents dissolve in urine on paper and react with glucose in urine.  The darkness of color can be correlated with amount of glucose present in urine.  Because Glucose oxidase enzyme can act only on beta-D Glucose, other reducing substances do not give this test positive.
  • 54.  Thus, compounds like Vitamin C, Aspirin utilize H2O2 produced in the reaction.  Due to lack of H2O2, Peroxidase can not oxidize dye. Thus, glucose may not be detected even if present, if urine contain Vitamin C or Aspirin in large amount. This phenomenon is called false negative result.
  • 55.
  • 56. Osazone Formation  All reducing sugars will form osazones with excess of phenyl hydrazine when kept at boiling temperature.  Glucose, Galactose and Fructose will produce the same needle-shaped crystals. Why?
  • 57.
  • 58. Molisch’s test  All carbohydrates when treated with conc. sulphuric acid undergo dehydration to give fufural compounds. These compounds condense with Alpha-napthol to form colored compounds.  Molish test is given by sugars with at least five carbons because it involves furfural derivatives, which are five carbon compounds.
  • 59. Purple ring at junction
  • 60. Fehling’s test Same principle as benedicts test Fehling’s A contains 7% copper sulphate and Fehling’s B contains sodium potassium tartarate.
  • 61. Barfoed’s test  This test is based on the same principle as Benedict’s test.  But, the test medium is acidic.  In acidic medium (pH 4.6) monosaccharides react faster than disaccharide.  Barfoed’s reagent contains copper acetate in glacial acetic acid.
  • 62. Scanty Red precipitate at bottom of tube
  • 63. Seliwanoff’s test  Seliwanoff’s test is a chemical test which distinguishes between aldose and ketose sugars.  Ketohexoses like fructose on treatment with HCl form 5- hydroxymethylfurfural, which on condensation with resorcinol gives a cherry red complex.
  • 65. Oxidation The glucuronic acid is used by the body for conjugation with insoluble molecules to make them soluble in water for detoxification purpose and also for synthesis of heteropolysaccharides.
  • 66. Reduction to Form Alcohols  When treated with reducing agents hydrogen can reduce sugars. Aldose yields corresponding alcohol.  Glucose is reduced to sorbitol  mannose to mannitol  fructose becomes sorbitol and mannitol  Galactose is reduced to dulcitol and  ribose to ribitol.
  • 67. Significance of reduction  Sorbitol, mannitol and dulcitol are used to identify bacterial colonies.  Mannitol is also used to reduce intracranial tension by forced diuresis.  The osmotic effect of sorbitol produces changes in tissues when they accumulate in abnormal amounts, e.g. cataract of lens.
  • 69.
  • 70. Lactulose • Lactulose is also known as beta-D- galactopyranosyl-D-fructofuranose. • Used in constipation
  • 71. Glycosides  The hydroxyl group of anomeric carbon of a carbohydrate can join with a hydroxyl group of another carbohydrate or some other compound to form a glycoside and the bond so formed is known as glycosidic bond.  eg. R-OH + HO-R’ R-O-R' + H2O  The non-carbohydrate moiety is known as aglycone –phenol, sterol, glycerol and methanol.  Glycosidic bond can be N-linked or, O- linked.
  • 72.
  • 73.
  • 74. Biomedical importance of glycosides  Cardiac Glycosides –Digoxin, Digitoxin ◦ Used in cardiac insufficiency. ◦ Stimulate cardiac muscle contraction. ◦ Contain steroids as aglycone component.  Ouabain –Sodium pump inhibitor.
  • 75.  Streptomycin ◦ Antibiotic ◦ Given in Tuberculosis  Phloridzin ◦ cause renal damage, glycosuria. ◦ Blocks the transport of sugar across the mucosal cells of small intestine & also renal tubular epithelium.
  • 76. Formation of Esters  Esterification of alcoholic groups of monosaccharides with phosphoric acid is a common reaction in metabolism.  Examples :Glucose-6-phosphate, and Glucose-1-phosphate.  ATP donates the phosphate moiety.
  • 77.
  • 78. Amino sugars Amino groups may be substituted for hydroxyl groups of sugars to give rise to amino sugars
  • 79. Importance Amino sugars Found in Glucosamine Hyaluronic acid, heparin and blood group substances Galactosamine Chondroitin sulphate of cartilage, bone and tendons. Mannosamine constituent of glycoproteins N-acetylglucosamine (GluNac) and N- acetyl galactosamine (GalNac) constituents of glycoproteins, Mucopolysaccharide and cell membrane antigens.
  • 80. Deoxy Sugars Oxygen of the hydroxyl group may be removed to form Deoxy sugars
  • 81. • 2-deoxy D-ribose is important part in DNA.
  • 83. Starch  It is the reserve carbohydrate of plant kingdom  Sources: Potatoes, cereals (rice, wheat) and other food grains.  Starch is composed of amylose and amylopectin.
  • 84.
  • 85.  Amylose is made up of glucose units with alpha-1,4 glycosidic linkages to form an unbranched long chain. Water soluble.  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. The branching points are made by alpha-1,6 linkage
  • 86. Iodine test for starch  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 nonreducing because the free sugar groups are negligible in number.
  • 87. Hydrolysis of starch  Amylodextrin = violet color with iodine and is non-reducing.  Erythrodextrin = red color with iodine and mildly reduce the Benedict's solution.  Achrodextrins = no color with iodine, reducing)  Maltose = (no color with iodine, but powerfully reducing) Short time to long time
  • 89.  It is the reserve carbohydrate in animals. It is stored in liver and muscle.  Liver glycogen stores increase during the well-fed state , and are depleted during a fast.  Glycogen is composed of glucose units joined by alpha-1,4 links in straight chains. It also has alpha-1,6 glycosidic linkages at the branching points.  Glycogen is more branched and more compact than amylopectin.
  • 90. Liver and muscle glycogen
  • 91. Cellulose  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 hydrolyzed by the enzyme cellobiase. But this enzyme is absent in animal and human digestive system, and hence cellulose cannot be digested.
  • 92. Importance Fiber can absorb 10–15 times its own weight in water, drawing fluid into the lumen of the intestine Increasing bowel motility 1.Decrease the risk for constipation It is a major constituent of fiber, the nondigestable carbohydrate.
  • 94. Delays gastric emptying and can result in a sensation of fullness 4. Reduced peaks of blood glucose following a meal Can bind various toxic substances including carcinogens & eliminate them in faecal matter 3.Decreases chances of some cancers
  • 95. Inulin  It is a long chain homoglycan composed of D-fructose units with repeating beta-1,2 linkages.  It is the reserve carbohydrate present in various bulbs and tubers, such as onion, garlic.  It is clinically used to find renal clearance value and glomerular filtration rate.
  • 96. Dextrans  These are highly branched homopolymers of glucose units with 1-6, 1-4 and 1-3 linkages. They are produced by micro- organisms.  Since they will not easily go out of vascular compartment, they are used for intravenous infusion as plasma volume expander for treatment of hypovolemic shock.
  • 97. Dextrose, Dextrin and Dextran are different  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.
  • 98. Chitin  It is present in exoskeletons of insects.  It is composed of units of N- acetylglucosamine with beta-1,4 glycosidic linkages.
  • 100. Agar  Agar = The linear polysaccharide Agarose + agaropectin  It is dissolved in water at 100ºC, which upon cooling sets into a gel. Agarose is used as matrix for electrophoresis.  Agar cannot be digested by bacteria and hence used widely as a supporting agent to culture bacterial colonies.
  • 102.  Because of their large number of negative charges, these heteropolysaccharide chains tend to be extended in solution. They repel each other, and are surrounded by a shell of water molecules. When brought together, they “slip” past each other.  This produces the “slippery” consistency of mucous secretions and synovial fluid.
  • 103. This property contributes to the resilience of synovial fluid and the vitreous humor of the eye
  • 104.
  • 105. GAGs Composition Tissue distribution Functions Hyaluronic acid D-glucuronic acid and N-acetyl D- glucosamine Connective tissue Synovial fluid Vitreous humor Gel around ovum lubricant and shock absorbant in joints Chondroitin sulphate D-glucuronic acid and N- acetyl D-galactosamine 4-sulfate. bone, cartilage, Tendons,heart valves and skin. Helps to maintain the structure And shapes of tissues Dermatan sulfate D-Iduronic acid and N-acetyl D-galactosamine 4 –sulfate. Skin Helps to maintain shapes of tissues Keratan sulphate galactose and N-acetyl glucosamine cornea tendons Keeps cornea Transparent Heparin sulphated glucosamine and glucuronic acid or iduronic acid blood, lung, liver ,kidney, spleen Anticoagulant Clearing factor
  • 106. Hyaluronic acid N-Acetyl-glucosamine → beta-1, 4- Glucuronic acid → beta-1-3-N-Acetyl glucosamine and so on.
  • 107. Hyaluronidase Breaks b(1-4 linkages) in hyaluronic acid. Present in high concentration in testes, seminal fluid, and in certain snake and insect venoms. Hyaluronidase of semen clears the gel (hyaluronic acid) around the ovum allowing a better penetration of sperm into the ovum. Serves important role in fertilization Hyaluronidase of bacteria helps their invasion into the animal tissues.
  • 108. Chondroitin sulphate glucuronic acid → beta-1,3-N-acetyl galactosamine sulfate → beta-1, 4 and so on
  • 109. Dermatan sulfateDermatan sulfate L-iduronic acid and N-acetylgalactosamine in beta-1, 3 linkages
  • 110. Keratan sulphate  Only GAG not having Uronic acid.
  • 111. Heparin It contains repeating units of sulphated glucosamine → alpha-1, 4-L-iduronic acid or glucuronic acid → and so on
  • 112.  Heparin is an anticoagulant( prevents blood clotting).  Heparin helps in the release of the enzyme lipoprotein lipase which helps in clearing the turbidity of lipemic plasma.  Lipoprotein lipase breaks TG in glycerol and FFA.
  • 113. HSEN Heparan sulphate Capillary On capillary endothelial wall surface Lipoprotein lipase Heparin displaces lipoprotein lipase from heparan sulphate binding site hence clearing factor
  • 114. Proteoglycans and Glycoproteins  Proteoglycans: When carbohydrate chains are attached to a polypeptide chain.  Glycoproteins: Carbohydrate content ≤ 10%.
  • 116. Glycoprotein Major function Glycophorin glycoprotein of erythrocytes cell membrane Collagen Structure of cartilage and bone Ceruloplasmin Transport protein Immunoglobulin Defense against infection Intrinsic factor Absorption of vitamin B12 Fibrinogen Blood clotting