3. *The living matter is composed of mainly six elements
carbon 50%
hydrogen 10%
oxygen 20%
nitrogen 8.5%
phosphorus 2.5% and
sulfur 0.8%.
These elements together constitute about 90% of the dry
weight of human body.
Several other functionally elements are
Ca 4%, K 1%, Cl 0.4%, Mg 0.1%, Fe
0.01%, Cu 0.1%, Co 0.3%, Na 0.4%, I
0.00005%, and Mn 0.001% .
4. Electrolytes are also play important role
K+, Na+, Cl-, Mg,2+ Fe2+, I-.
Biomolecules are
DNA ( Deoxynucleotide)
RNA (Ribonucleotide)
Proteins, (amminoacids),
Polysaccharides (glucose)
and Lipids. (Fatty acids)
Chemical composition for a human body weight is 65kg
the percentage of biomolecules is
protein-17%,
Fat-13.8%,
carbohydrates-1.5%,
water- 61.6% and minerarals-6.1%.
5. CARBOHYDRATES
* Carbohydrates are the widely distributed compound in
plants and animals kingdoms.
* Plants can be build up carbohydrates from carbon dioxides and
water in present of light in the chloroplast cell by photosynthesis.
6CO2 + 6H2O C6H12O6 + 6O2
* Many plants and animals contain large quantities of
carbohydrates as reserve food material
* Simples carbohydrates are also known as sugar or saccharides
and ending names of most sugars is ose.
SUN light
energy
(glucose)
6. General characteristics
• The term carbohydrate is derived from the
french word : hydrate de Carbone, that composed
with C, H, and O
• (CH2O)n when n = 5 then C5H10O5
• not all carbohydrates have this empirical formula:
deoxysugars, aminosugars
• carbohydrates are the most abundant organic
compounds found in nature.
7. Different types of carbohydrates
Mono saccharids (glucose, galactose and fructose)
Oligosaccharids (maltose, lactose and sucrose)
• Polysaccharides (starch, cellulose, inulin, gums)
• Glycoproteins and proteoglycans (hormones, blood group
substances, antibodies)
• Glycolipids (cerebrosides, gangliosides)
• Glycosides
• Mucopolysaccharides (hyaluronic acid)
• Nucleic acids
8. Functions
• sources of energy(dietary source)
• intermediates in the biosynthesis of other basic
biochemical's like (fats and proteins)
• associated with other, such as glycosides, vitamins and
antibiotics)
*form structural tissues in plants and in microorganisms.
. (cellulose, lignin, murein)
• participate in biological transport, cell-cell recognition,
activation of growth factors, modulation of the immune
system
carbohydrates are participate in a wide range of functions
9. Sugars Non Sugars
Sweet in taste Tasteless
Soluble in water Insoluble in water
Crystalline in appearence Amorphous in nature
Example: Glucose, Sucrose Example: Starch
General Classification:
Carbohydrates are 3 types
1.Based on their nature
2.Based on their Reactivity
3.Based on their number
•Based on their nature, carbohydrates are of two types namely Sugars and Non Sugars
10. Reducing Sugars Reducing Non Sugars
Free Functional Groups Functional groups not free
Can participate in chemical
reactions
Will not participate in
chemical reaction
Eg: Glucose Eg: Sucrose
•Based on their Reactivity:
Carbohydrates are of two types namely
1. Reducing sugars: ( containing free functional group)
2.Non reducing: (no free functional group) carbohydrates.
•
11. Sugars Non Sugars
Monosaccharides Single Sugar Unit
Disaccharides Two Monosaccharide units
Oligosaccharides Three to Six
Monosaccharide units
PolySaccharides More than six
Monosaccharide units
•Based on their Composition or based on their number:
• Number of individual sugar units present, carbohydrates are of four types namely
12. Classification of carbohydrates
• Monosaccharides (monoses or glycoses)
• Trioses, tetroses, pentoses, hexoses
(glucose, galactose and fructose)
• Oligosaccharides/ Disaccharides
• Di, tri, tetra, penta, up to 9 or 10
• Most important are the disaccharides
(lactose, maltose, sucrose)
• Polysaccharides or glycans
• Homopolysaccharides
• Heteropolysaccharides
• Complex carbohydrates
(starch, glycogen, cellulose)
13. Monosaccharides
• Monosaccharides contain a single polyhydroxy
aldehyde or ketone unit also known as simple sugars
(saccharo is Greek for“sugar”) (e.g., glucose,
galactose and fructose).
• Monosaccharides are classified according to the
number of carbon atoms they contain 1carbon
/2carbon , whether aldose CHO or ketosC=O:
• No. of Class of carbons Monosaccharide
3C triose
4C tetrose
5C pentose
6C hexose
14. • Most of monosaccharoids (99%) are straight
chain compounds
•
Triose : Those with 3 carbon atoms, are called triose
e.g. glyceraldehyde is an aldotriose and dihydroxy
acetone is a kettriose .
•
Significance:
These two sugars are intermediates in Glycolysis pathway concerned with conversion of
glucose to pyruvate
16. Tetroses:
•Those with four are called tetroses such as erythrose
(Aldotetrose) and erythrulose (Ketotetrose)
Biological significant:
This is intermediate in HMP shunt pathway, associated with Inter conversion of sugars
17. Pentoses
Those with five carbon atoms are called pentose's viz. Aldopentoses such as xylose and
ribose and ketopentoses such as xylulose and ribulose etc.
•1. Ribose is an essential constituent of RNA and Vitamin riboflavin
•2. Xylose is an essential constituent of Gums and Glycoproteins
•3. Ribulose and Xylulose are intermediate in HMP shunt pathway
18. Hexoses:
Those with six carbon atoms are called hexoses aldohexoses ketohexose.
*Glucose is the most readily metabolizable sugar present in the human body. Glucose
sugar is called sugar fuel of life. *Fructose is the sweetest sugar, it’s
constituent of honey.
*Mannose is an important constituent of gums and glycoproteins
Galactose is considered as the backbone of lipids.
.
19. Properties of monosaccharids
• Differences in structures of sugars are
responsible for variations in properties
• Physical
• Crystalline form; solubility; rotatory power
• Chemical
• Reactions (oxidations, reductions, condensations)
• Physiological
• Nutritive value (human, bacterial); sweetness;
absorption
20. Physical Properties of Monosaccharides:
• Most monosaccharides have a sweet taste (fructose
is sweetest; 73% sweeter than sucrose).
• They are solids at room temperature.
• They are extremely soluble in water:
– Despite their high molecular weights, the
presence of large numbers of OH groups make
the monosaccharides.
– Glucose can dissolve in minute amounts of water
to make a syrup (1 g / 1 ml H2O).
21. D- AND L- Configuration
*Biologically active Sugars are normally belongs to
two series namely D and L Series.
*D sugars are biologically active and L sugars are
biologically inactive.
* Differentiate a D sugar from a L sugar the
penultimate carbon or the last but one carbon
atom is considered.
*In the D sugars OH group is on the penultimate
carbon is on Right
*In the L sugars OH group is on the penultimate
carbon is on left
*All D sugars are obtained from D- Glyceraldehyde
and L sugars are from L-Glyceraldehyde.
23. Organic Compounds Optical activity
Optically Inactive (Achiral) Optically Active (Chiral)
Measurement of Optical Activity :
Polarimeter
COOH
CH3
OH
H
COOH
COOH
OH
H
OH
H
24. Chiral And without Chiral Compounds
Many molecules are chiral with chiral centers
There are several molecules which are
Achiral with chiral centers
COOH
CH3
OH
H
COOH
COOH
OH
H
OH
H
25. Optical Activity:
Most biologically important molecules are chiral
and hence are optically active.
• A levorotatory (–) substance rotates polarized light
to the left. [E.g., l-glucose; (-)-glucose]
• A dextrorotatory (+) substance rotates polarized
light to the right. [E.g., d-glucose; (+)-glucose]
• Molecules which rotate the plane of of polarized
light are optically active.
•
when a compound is a equal mixture like dextroro and
levo, then the final rotation comes to zero. Such a mixture is
called Racemic Mixture.
E.g.; Glucose is dextrorotatory and Fructose is
levorotatory.
27. polarimetry
Magnitude of rotation depends upon:
1. the nature of the compound
2. the length of the tube (cell or sample container)
usually expressed in decimeters (dm)
3. the wavelength of the light source employed;
usually either sodium D line at 589.3 nm or
mercury vapor lamp at 546.1 nm
4. temperature of sample
5. concentration of analyte in grams per 100 ml
30. Specific Rotation [α]D
[α] = α / cl
a = observed rotation
c = concentration in g/mL
l = length of tube in dm
Dextro rotation designated as “d” or (+), clockwise
rotation
Laevo rotation designated as “ l ” or (-),
counter anti clockwise rotation
31. Specific Rotations of some Common
Organic Compounds
Compound [a]D No. of Chiral
centres
Penicillin V +233.0 3
Sucrose +66.5 10
Camphor +44.3 2
Cholesterol -31.3 8
Morphine -132.0 5
32. Optical isomerism
• A property exhibited by any compound whose
mirror images are non-superimposable
• Asymmetric compounds rotate plane polarized
light
35. Epimerization:
*The shift of configuration at a specific carbon atom other than
C1, C5 and C6 with respect to Glucose is called Epimerization and
the resulting compounds are called. epimers.
.
In the structure of Glucose,
when there is a shift of
configuration at 2nd carbon
atom Mannose is formed
when there is a shift of
configuration at 3rd carbon
atom Allose is formed
when there is a shift of
configuration at 4th carbon
atom Galactose is formed.
39. Structure of Fisher and Haworth projection
Cyclic & Open Ring Structures of Monosaccharides
Anomerization
Mutarotation
Osazone
Reactions of monosaccharides
Monosaccharide
40. Structural representation of sugars
• Fisher projection:
straight chain representation
• Haworth projection: simple ring form
• Conformational representation: chair and boat
configurations
41. Rules for drawing Haworth projections
• draw either a six or five-membered ring including
oxygen as one atom
• pyranose furanose
• most aldohexoses are six-membered
• aldotetroses, aldopentoses, ketohexoses are 5-
membered
O O
42. • Next, number the ring clockwise starting next to the
oxygen
• if the substituent is to the right in the Fisher projection,
it will be drawn down in the Haworth projection (Down-
Right Rule)
O O
1
2
3
4
5
1
2
3
4
44. D-ribose and other five-carbon
saccharides can form either
furanose or pyranose structures
45. Chair and boat conformations of a pyranose sugar
If the substituents attached to the ring carbons that
Extend parallel to the symmetric axis are said to be axial(a)
If extend outward from the axis are said to be equatorial(e)
2 possible chair conformations
of b-D-glucose
46. Chair Conformations of Glucopyranose Anomers
b-D-(+)-Glucopyranose a-D-(+)-Glucopyranose
up (top)
beta
down (bottom)
alpha
O
OH
HO
HO
OH
OH
O
OH
HO
HO
OH
OH
Conformational Glucopyranose
47. Haworth Projections of Glucopyranose Anomers
O
CH2OH
OH
OH
OH
OH
O
CH2OH
OH
OH
OH
OH
b-D-(+)-Glucopyranose a-D-(+)-Glucopyranose
up (top)beta
down (bottom)
alpha
In D-sugars, the OH group at the anomeric position is drawn down
for a and up for b.
In L-sugars, the OH group at the anomeric position is drawn up a
and down for b
48. Cyclic Structures of Monosaccharides:
*Haworth was proposed a method of pyran ring or furan ring
formation.
* That sugars are with six member rings in pyran form can be
called pyranohexoses ( eg. Gluco pyranose)
*Another on furan form are furano hexoses (eg.
Fructofuranose).
* pyranose forms is more stable, involves C1 and C5
carbons.
The less stable ring form. involves C1 and C4 carbons
49. 49
23.7: Cyclic Forms of Carbohydrates: Pyranose Forms.
glucopyranose
ribopyranose
Note: the pyranose forms of carbohydrates adopt chair conformations.
50. Linear glucose Open ring of glucose
hemiacetal
Open Ring Structures of Monosaccharides
*The linear structures of glucose and fructose could be
converted into open ring structures through intramolecular
rearrangement.
*Glucose undergoes rearrangement between C1and C5 to form
hemiacetal and fructose undergoes rearrangement between C2
and C5 to form hemiketal.
f fructose Fructose Open ring hemiketal.
51. Anomerization
•The respective carbons functional groups are changed to one
configuration(α and β) to another configuration is called
Anomerization
Glucose exists in two anomeric forms namely α-alpha and β beta
D-glucose.
*which the OH group points down (α-hydroxy group) and one in which
the OH group points up (β-hydroxy group) and carbon-1 is called the
anomeric carbon
α-D-Glucose D-Glucose β-D-Glucose
52. Mutarotation
*Reducing sugars have two optical rotation +112.20 &
+18.70 an equilibrium point.
*It is known that glucose is present in two isomeric
forms. α–D & β-D glucose.
*When any of these solutions is allowed to attain
equilibrium, the specific rotation values of both forms of
glucose attain a constant value of +52.70.
This change in specific rotation such that solution attains
a constant value is called Mutarotation.
53. 53
When the pure anomers are dissolved in water they undergo
mutarotation, the process by which they return to an
equilibrium mixture of the anomer.
a-D-Glucopyranose (36%)
(a-anomer: C1-OH and
CH2OH are trans)
b-D-Glucopyranose (64%)
(b-anomer: C1-OH and
CH2OH are cis)
[a]D +18.7°
[a]D +112.2°
acid-catalyzed mechanism: p. 1037
55. Reactions of monosaccharides
• Carbonyl reactions:
• Osazone formation
• Cyanohydrin reaction
• Reduction
• Oxidation
• Action of base
• Action of acid
• Ring chain tautomerism
• Alcohol reactions
• Glycoside formation
• Ether formation
• Ester formation
56. Formation of osazones
• it’s for the identification of sugars
• consists of reacting the monosaccharide with
phenylhydrazine
• a crystalline compound with a sharp melting point will
be obtained
• D-fructose and D-mannose give the same osazone as D-
glucose
Each sugars have different shapes, such as
--glucose, mannose, fructose=needle shaped crystals
--xylose= long fine needles
--Maltose=sunflower shaped crystals
--lactose= puff shaped crystals
57.
58. Cyanohydrin formation
• reaction of an aldose with HCN
• These on hydrolysis with suitable reagents give two
sugar acids
• used to increase the chain length of monosaccharide
(sugar molecules contain one more than the original
one)
• known as the Fischer-Kiliani synthesis
59. Oxidation reactions of Monosaccharides:
*Glucose undergoes mild oxidation in the presence of mild oxidizing
agents like Bromine in aqueous KOH to form Gluconic acid.
*Glucose undergoes in the presence of strong oxidizing agents like
Conc. nitric acid to form saccharic acid.
*under in-vitro in the presence of glucose oxidase (Aspergilus Niger) to
form glucuronic acid.
60.
61. Reduction reactions of Monosaccharides:
Glucose undergoes reduction at the functional group
carbon in the presence of zinc amalgam or sodium
amalgam to form an alcohol called sorbitol.
*Fructose undergoes reduction at the functional group
carbon to form mixture of alcohols called sorbitol and
mannitol.
62. *Ribose undergoes reduction at the functional
group carbon to form an alcohol called Ribitol that
forms the backbone of the vitamin Riboflavin.
*Galactose undergoes reduction at the functional
group carbon to form an alcohol called Dulcitol
that is responsible for the development of
cataract.
Sructures of some sugar alcohols
63. Enolization
• Sugars are weak acids, in present of dilute NaOH
solution for long time it under goes tautomerization
and give D-mannose, D-fructose and can form salts
• The reaction is known as the Lobry de Bruyn-Alberta
von Eckenstein reaction
64. Glucose measurement methods
• Most methods are enzymatic methods
– 3 enzyme systems are currently used to
measure glucose:
• Glucose oxidase
• Glucose dehydrogenase
• Hexokinase
• These reactions produce either a product that can
be measured photometrically
67. Condensation reactions:
If two different reactant molecules are reacted with
each other to form a single product.
That type of reaction are referred as condensation.
68. Special monosaccharides: deoxy sugars
• These are monosaccharides which lack one or
more hydroxyl groups on the molecule
• one quite ubiquitous deoxy sugar is 2’-
deoxy ribose which is the sugar found in DNA
• 6-deoxy-L-mannose (L-rhamnose) is used as a
fermentative reagent in bacteriology
76. Oligosaccharides
• Carbohydrates that are made up of two
similar or dissimilar monosaccharides are
called disaccharides.
• In other words Carbohydrates that on
hydrolysis produces two similar or dissimilar
monosaccharides are called disaccharides.
• Based on their composition the
disaccharides are of two types namely
1.homo 2. hetero disaccharides
77. • 1. Homo disaccharides such as Maltose
made up of Glucose and Glucose
(Glucose+ Glucose)
• 2. Hetero disaccharides such as lactose
made up of glucose and galactose
(glucose+galactose)
• Sucrose made up of glucose and
fructose.
78. Maltose
*Maltose is also called Malt sugar and is an
important constituent of germinating seeds .
*Two glucose units which are joined
together by α 1,4 linkages.
79. *It is not produced in the body under
normal circumstances
But it is obtained as an intermediate
produced during acid hydrolysis of starch.
*During the enzymatic hydrolysis in
present of Maltase, it is converted to
Glucose and Glucose
80. Source: does occur in plants but normally
obtained from cows milk
*Lactose is a reducing Disaccharide made up
of galactose and glucose.
*Lactose can be enzymatically broken down
into Galactose and Glucose by the enzyme
Lactase.
Lactose
81. • In lactose, Galactose & Glucose are found
together by β 1, α 4 linkage where the sugar
is β with respect to C1 of Galactose.
Used as:
=tablet diluent esp in antibiotic preparations.
=nutrient in infant foods
=less sweet than sucrose
82. Sucrose:
Sucrose is also called as cane sugar or table or
invert sugar.
Sucrose is industrially important as it is involved
in the manufacture of ethanol through the
action of Invertase & Zymase.
Used pharmaceutically to make syrups, troches
83. • It is involved in a glycosidic linkage is made
up of α-D gluco pyranose unit & β-D fructo
furanose unit joined together by α –β 1, 2
linkages.
84. Sucrose +66.5o before hydrolysis is concerned as
D rotatory - compound but on hydrolysis it forms
D glucose +52.5o; & L rotator fructose–92o & since the
L rotation of fructose is greater than the D glucose.
This process is called inversion and because of this
change in rotation from D to L Form sucrose is called an
invert sugar.
Sugar cane Sugar beet
86. Polysaccharides
Several mono sacchaarides molecules
combine to form polysaccharides
In other words Carbohydrates that on final
hydrolysis produces a single monosaccharide
and disaccharides are called polysaccharides.
These are not soluble in the water and not
sweet
They don’t show any properties of aldehyde
and ketone
87. Classification
Based on their compositions polysaccharide are
two type
1.Homo polysaccharides.
2. heteropolysaccharids
If all monsaccharides units same in the
polysaccharides is called homo polysaccharides
* If the homopolysaccharide on hydrolysis yields
glucose only the Polysaccharide is called
Glucosan / Fructose only is called Fructosan.
E.g. Starch, cellulose and Glycogen.
88. Polysaccharide is made up of a sugar and sugar
derivatives are called Hetero polysaccharides or
Muco polysaccharides or Heteroglycans or Glycosyl
amino glycans.
E.g. Heparin, Chondroitin sulphate.
Hetero polysaccharides
90. Starch
Starch is wide spread in nature and is the reserve
carbohydrate in plants.
It is also an important constituent of most of the
tuberous plants like potato, sweet potato etc.
Starch is basically made up of two units namely
the amylose & amylopectins.
composed of 10 – 30% a-amylose and 70-90%
amylopectin depending on the source
91. The amylose units are considered as soluble
fraction of starch. {Partial part}
The basic color reactions of starch i.e., blue
colour solution with Iodine is due to these
amylose units present in starch.
The chains are of varying length, having
molecular weights from several thousands to
half a million
92. suspensions of amylose
in water adopt a helical
conformation
iodine (I2) can insert in
the middle of the
amylose
helix to give a blue color
that is characteristic and
diagnostic for starch
93.
94. Amylose and amylopectin are the 2 forms of starch.
AMYLOSE
The unbranched amylose units in starch are joined
through α 1, 4 glycosidic linkages.
Amylopectin units are present to the extent of 80% of
the entire starch molecule.
95. Amylopectin
These are the branched and insoluble units of starch.
The amylopectin units in starch are joined together by
α 1,6 linkage.
When treated with Iodine they give pale purple colored
solution.
96. Amylopectin is a highly branched structure, with
branches occurring every 12 to 30 residues
97. Cellulose:
It is the chief constituent of fibrous part of the plant and is
the major component of plant cell wall.
It is considered as most abundant carbohydrate present in
nature.
It is made up of repeated units of glucose that are joined
by β-1,4 linkages..
100. Cellulose cannot be utilized or not digested by
human beings, because of the absence of
cellulase enzyme in the gastrointestinal tract.
It is nitrated to form nitro-cellulose that is used in
the manufacture of explosive substances.
It can be acylated to form cellulose acetate, which
is used in manufacture of photographic plates.
101. • Microcrystalline cellulose : used as binder-
disintegrant in tablets
• Methylcellulose: suspending agent and bulk
laxative
• Sodium carboxymethyl cellulose: laxative
• Cellulose acetate: rayon; photographic film;
plastics
• Nitrocellulose: explosives; collodion (pyroxylin)
Products obtained from cellulose
102. Glycogen
*It is present in animals and sometimes referred as
animal starch also.
* Glycogen is not found in the plants, except fungi
and yeast.(non chlorophil)
*contains both a(1,4) links and a(1,6) branches at
every 8 to 12 glucose unit
* Glycogen is synthesized in the body from glucose
through glycogenesis
*It is present in the liver it acts as a storehouse of
glucose and by being present in muscle it supplies
energy in order to do work
104. Glycosaminoglycans
• They are the polysaccharide chains of proteoglycans
• They are linked to the protein core via a serine or
threonine (O-linked)
• The chains are linear (unbranched)
• The glycosaminoglycan chains are long (over 100
monosaccharides)
• They are composed of repeating disaccharides
106. Mucopolysaccharides
--The polysaccharides are consisting of different type of sugars or
their derivative are known as heteropolysaccharides and they are
also called heteroglycans.
--Mucopolysaccharides and heteroglycons are made up of repeating
sugar units of sugar derivative namely amino sugars and uronic
acids as the principal components
These are more commonly known as glycosamino glycans (GAG)
In (GAG) Structure there will be acetylated amino groups, sulphate
groups and carboxylic groups
The acidity of GAG’s is due to the presence of sulphate and
carboxylic groups.
107. Hyaluronic acid:
Hyaluronic acid was first isolated from the Vitreous Humor by
Meyer and Palmer and later from the synovial fluid, skin,
umbilical cord.
Hyaluronic acid is present in bacterial and is widely distributed
various animals and tissues such as loose connective tissue
and forms a gel around the ovum
This serve as lubricant and shock absorbent in joints
The enzyme present in the semen namely hyaluronidase
degrade the gel and allows effective penetration of sperms into
ovum
108. Hyaluronic acid consists of an unbranched chain of repeating
disaccharids units containing Glucuronic acids and N-
Acetylglucosamines
Hyaluronic acid is made up of with N-Acetyl D-Glucosamine and
D-Glucuronic acid are linked with b1, α4 and b1,α3 glycosidic
linkages.
109. Chondroitin sulphate A:
It is a sulphate containing mucopolysaccharide.
Chondroitin sulphate A is found to occur in the cartilage adult
bone and cornea .
It is made up of N-Acetyl galactosamine-4-sulphate and
Glucuronic acid are linked with b1,4 and b1,3 glycosides linkages.
Chondroitin is found in tendons, cartilage and other connective tissues
110. Heparin:
Heparin is found in the granules of mast cells of the
liver lungs and skin
It was also isolated from the lung, thymus, spleen
and blood.
Heparin is a polymer (containing repeated
disaccharids are present ) of D-glucuronic acid(GlcUA)
and D-Glucosamine (GlcN) are joined by α1,4
linkages.
