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Biomolecules Notes
Biomolecules Notes
biochenmistry.
CARBOHYDRATES
Hydrates of carbon having general formula, C,(H,O), is known carbohydrates.
as
For example. glucose (CH,0) fits into the general formula, C(H,O)
not considered as
But all the compounds having general formula C,(H,O), are
fits into this general
carbohydrates. For example, Ethanoic acid (CHCOOH)
but it is not a carbohydrate. Also, all carbohydrates do
not
formula, C(H,O)2,
fit into the general formula C(H,O), e.g., rhamnose (CH,20). Chemically
or ketones
carbohydrates are defined as optically active polyhydroxy aldehydes
or the compounds which produce such
units on hydrolysis. Carbohydrates are
which are sweet to
also known as saccharides. Some of the carbohydrates
taste, are also called sugars.
Classification of Carbohydrates :
can be divided
On the basis of their behaviour upon hydrolysis, carbohydrates
intothree main groups
into
) Monosaccharides : A carbohydrate which cannot be hydrolyzed
ketone is called
simpler unit of polyhydroxy aldehyde
or
(CHO,), + nH,O
nCHO,
Starch or Cellulose Glucose
Sugar and non-sugars : In general monosaccharides and oligosaccharides, are crystalline solids, soluble in
wate and sweet to taste, are collectively known as sugars. The polysaccharides, on the other
hand, ar
amorphous insoluble in water and tasteless, are known as non-sugars.
Reducing and non-reducing carbohydrates The carbohydrates containing free aldehydic (-C-H) o
ketonic (C =
0) group
reduce Fehling's solution and Tollen's reagent are known
can as
reducing
carbohydrates. All monosacchanides whether aldose or ketose are reducing in nature.
The carbohydrates in which the reducing parts are not free cannot reduce Fehling's solution and Tollen's reagent
are known as non-reducing carbohydrates.
For example, in sucrose reducing part of glucose is bonded with the reducing part of fructose. So this
disaccharide is non-reducing. All disaccharides except sucrose are reducing in nature.
All polysaccharides like starch, cellulose, glycogen etc. are non-reducing carbohydrates.
Monosaccharides
fa monosaccharide contains an aldehyde group, it is known as an aldose and if it contains keto
a group,it
is known as a ketose.
Preparation of Glucose
H nCHO
(CHp),+ nH,O 393 K; 2-3 bar
Starch or
Glucose
Cellulose
Structure of Glucose
cellulose etc. It is
Glucose is an aldohexose and is the
monomer of many larger carbohydrates like starch,
on the Earth.
the most abundant organic compound
CHO CH N-OH
CN
CHO CHK
OH
HCN
(CHOH) (CHOH) Cyanohydrin of glucose
(1 eq.)
CHOH CHOH
acid upon oxidation with mild-oxidising agents like Bromin water, Tollen's reagent, Fehling's solution ete
CHO CoOH
Br,-Water
(CHOH), (CHOH) Gluconic acid
CH,OH CH,OH
CHO CHO
5(CH,CO),o
(Acetic anhydride)
(CHOH), (CH-0-C-CH)
O
CH,OH CH-O-C-CH,
This confirms the presence of five -OH groups attached to different carbon atoms in glucose.
6. Presence of Primary Alcoholic (CH,2 - OH) Group : On oxidation with nitric acid, glucose as well as
gluconic acid both yield the dicarboxylic acid, saccharic acid.
(CHOH)
HNO HNO
(CHOH) (CHOH).
7. Spatial Arrangement of -OH Groups: The exact spatial arrangement of 5- OH groups in glucose was
provided by Fischer after studying many other properties of it. The configuration of open chain structure
ofglucose can be represented by Fischer projection formula as
CHO
- OH
H
HO- -H
H -OH
H- OH
CH,OH
D(+)-Glucose
Glucose is corectly named as D(+) - Glucose. 'D' before the name of glucose represents the configuration
whereas+ represents dextrorotatory nature ofthe molecule. It should be noted that there is no direct
relation between D, L configurations with d and I or (+) or (-) notations.
Limitations of Open Chain Structure of Glucose
The open chain structure of glucose explains most of the properties of glucose except following ones
1. Although glucose has an aldehydic group. it does not give, 2, 4-DNP test, Schiff's test and also it de
not react with NaHSO, or NH, to form addition product.
2. The pentacetate of glucose formed upon acetylation of glucose, daoes not react with hydroxylamine, Thi
indicates the absence of aldehydic (-CHO) group.
3. The existence of glucose in a and B- anomeric forms could not be explained by the open chain structura
The a-form of glucose having m.p. 419 K is obtained by crystallising form of concentrated
solution of
glucose at 303 K while the B-form having m.p. 423 K is obtained by crystallising of hot and
saturated
aqueous solution at 371 K.
H-C-OH H HO-C-H
H OH H OH H OH
HO -H HO H HO HO
H OH H OH H4 OH
H H OH H
Pyran
Pyran is a six membered ring with one oxygen and five carbon atoms in the ring. The cyclic structure of glucose
is more correcty represented by Haworth structure as given t
CHOH CHOH
H H H
5 OOH
OH OH
HO 3 OH HO H
3
H OH H OH
a-D-(+)-Glucopyranose B-D-(+)-Glucopyranose
Fructose and Its Structure
Fructose is an important ketohexose. It is obtained by the hydrolysis of sucrose. On the basis of molecula
weight determination, elemental analysis and various reaction its molecular formula is found
to be H29, and
open chain structure of it can be written as
CH,OH
HO--H
HFOH
HFOH
CH,OH
D-(--Fructose
It contains a ketonic functional group at C-2 and six-carbon atoms in straight chain. Naturally occuring fructose
Furan
Furan is a five-membered cyclic compound with one oxygen and four carbon atoms.
HO-C-CHOH
HOH,C-C-OH
HO H HO H
H OH H OH
H H
CH,OH CH,OH
o-D-(--Fructofuranose B-D---Fructofuranose
structures as:
of fructose can be represented by Haworth
The cyclic structures of two anomers
1 6
HOH,C CHOH HOHC O OH
OH/OH H OH/CH,OH
HH 3 3
OH H OH H
a-D-(--Fructofuranose P-D-(--Fructofuranose
Ci2H22011
Lactose
»CsH1205+
Glucose
CsH120
Galactose
HO
C2H22011
Maltose
CgH20+CsH120s
Glucose Glucose
In disaccharides the two monosaccharides units are joined together by an oxide linkage formed by the loss
of a water molecule and the linkage is known as glycosidic linkage.
The disacharides may be reducing or non-reducing depending upon the position of linkage between the two
monosaccharide units.
() Sucrose
Sucrose is formed by the glycosidic linkage between C-1 of a-D-(+)-9lucose and C, of p-D-(-) fructose :
CH
H O H HOHC
H
**********
OH HO
HO
************ 3 4 CHOH
6
Glycosidic OH H
H OH linkage
As the reducing parts of glucose and fructose are involved in glycosidic linkage, sucrose is a non-reducing
sugar.
Sucrose is dextrorotatory in nature but upon hydrolysis it gives the equimolar mixture of D-glucose
(l+52.5) and D-fructose (o, = -92.4) which is laevorotatory. Thus the hydrolysis of sucrose changes
the sign of rotation, from dextro (+) to laevo () and the product so formed is known as invert sugar.
(i) Maitose : Maltose is formed by the glycosidic linkage between C-1 of one glucose unit to the C-4 of
another glucose unit.
6
CHOH CH,OH
H H H H
H H
OH H OH
HO
2 -0 OH
3
H OH H OH
() (11)
a-D-Glucose a-D-Glucose
Maltose
Maltose is a reducing sugar because the C-1 of second glucose unit is not involved in glycosidic linkage
and in solution it can show
reducing properties so it is a reducing sugar.
(ii) Lactose: Lactose is found in milk so it is also
known as milk sugar. It is formed by the glycosidic
linkage between C-1 of B-D-galactose unit and C-4 of
B-D-glucose unit.
6
CH,OH CH,OH
HO O. H
O OH
H
OH H B-linkage QH
H H
H OH H OH
B-D-Galactose B-D-Glucose
Lactose
Polysaccharides
Polysaccharides are long chain polymer of monosaccharides joined together by glycosidic linkages. For
example, starch, cellulose. glycogen etc. They mainly act as the food storage or structural materials.
Starch (CH,O), : Starch is the main storage polysaccharide of plants. High content of starch is found in
cereals, roots, tubers and some vegetables.
(CgH,OhasslaseC2H2,0,1 CH20g:D-glucose
Starch Maltose
Starch is polymer of a-D-(+) Glucose coming of two components namely Amylose and
a
is water soluble
Amylopectin. Amylose
component, which constitutes about 15 20% of starch. It is a straight chain polysaccharide
containing a-D-(+Hglucose units joined together by a-glycosidic linkage involving C-1 of one glucose unit and
C4 of the next. It can have 200 1000
o-D-(+-glucose units held by C1 C4 glycosidic linkage. -
a-Link o-Link
Amylose
Amylopectin isbranched chain
a
polysaccharide
insoluble in water. It constitutes about
80 85% starch. It is a branched chain
polymer of a-D-glucose units in which chain is formed by
C1-C4 glycosidic linkage whereas branching occurs by C1 C6 glycosidic linkage.
CH,OH CH,OH
H O,
OH H -0 OH
-link
H OH H OH
Branch at C
CH,OH CH CH,OH
H H H H
H H
OH OH O OH
H OH H OH H OH
-Link 0-Link
Amylopectin
Cellulose
Cellulose is a straight chain polysaccharide composed of only B-D-glucose units. In cellulose there is B-
glycosidic linkages between C-1 of one glucose unit and C-4 of the next glucose unit. Cellulose occurs mainly
in plants and it is the most abundant organic substance in plant kingdom. It is the chief constituent of the
cell walls of plants.
HOH,C
-o O
OH
HOHC
OH
OH
OH
HOH,C
B-links
OH
OH
Cellulose
Glycogen
Its structure is similar to amylopectin with more branching than in amylopectin. It is also known as animal
starch. In body, carbohydrates are stored as glycogen and when the body needs glucose, enzymes break the
glycogen down to glucose. Glycogen is present in liver, muscle and brain. It is also found in yeast and fung.
Importance of Carbohydrates
Carbohydrates are essential for life in both plants and animals. Carbohydrates are stored in plant as starch
and in animals as glycogen. Cell wall of bacteria and plant is made up of cellulose. Furniture used in daily
life, are made in the form of wood, clothe we wear is also made from cellulose in the form of
fromcellulose
cotton fibre.
PROTEINS
The term protcin is the
derived from Greek word Proteins' which means of prime importance. Proteins are high
molecular mass complex biopolymer of oa-amino acids present in all living cells. They occur in every part of the
body and form the fundamental basis of structure and functions of life.
Proteins are the most abundant biomolecules of theliving system. Chief sources of proteins are milk. cheese
pulses, peanuts, fish etc.
Amino Acids: The compoundcontaining-NH, and-COOH functional groups are known as amino acid, depending
upon the relative position of -NH, group with respect to -coOH group, amino acids are classified into a, B. 7,8
and so on amino acid. Hydrolysis of proteins gives only a-amino acids represented as
R-CH-COOH
NH2
Proteins may contain other functional groups also.
Nomenclature of a-Amino Acids: All a-amino acids have their trival names which generally reflect the property
of the
amino acids or their sources. For example, glycine is so named since it has sweet taste (in Greek, Glycos
means cheese)
meufa-G7lyine Aim
Classification of Amino Acids: Dependingupon the relative number of amino and carboxyl groups in the moiecuies
amino acids are classified as acidic, basic or neutral, depending upon the relative number of amino and carboxyi
groups. Equal numberof-NH, &-CoOH groups make the amino acid neutral, more -NH, group than-coo
group make the amino acid basicand more -COOH group than-NH, groupmake the amino acid acidic.> ( l u t a
Essential and non-essential amino acids:Theáminoacidswhich cannot be synthesized in the body are known
as
essential amino acids which must be taken through diet. The amino acids, which can be synthesized in the A e
body are known as non-essential amino acids. aud
Physical Properties of a-Amino Acids: Amino acids are generally colourless, crystalline, water-soluble, hign
melting solids.They behave like salts rather than simple amines or carboxylic acids due to the presence of both-
COOH&-NH, groups
n aqueous solution amino acid can exist as a dipolar ion known as zwitter ion if-COOH group loses H ion and-
O
between-C- and-NH-groups ofthe peptide bond.
H9
N
N N
RCH RCH RCH
H C-O-HNC0-H-NC-0
O-CR HCR HCR
N HCR N-H--O=C
N-H-O-C
N-H
RÇH RCH RCH
~H-NHCRCO-- HCR
0-H-N R
C C C
CO of an adjacent tum of the helix as shown above figure. In B-structure all peptide chains are strelcheo
out to nearly maximum extension and then laid side by side which are held together by intermolecular
H-bonds. The structure resembles the pleated folds of drapery and therefore is known as B-pleated sheet.
(3) Tertiary Structure: The tertiary structure of proteins represents overallfolding of the polypeptide chains i.e,
further folding of secondary structure. It gives rise to two major molecular shapes namely fibrous and globular.
The main forces which stabilizesthe 2°&3° structures of proteins are hydrogen bonds, disulphide linkages,
van der Waals and electrostatic forces of attraction.
(4) Quatermary Structure: Some of the proteins are composed of two or more polypeptide chains referred to as
Sub units. Ihe spatial arrangement of these subunits with respect to each other is known as quaternary
structure.
eseeo bee
egeed
Denaturation of Proteins :
The lossinbiological activity of a protein due to unfolding of globules and uncoiling of
helix is called denaturation of protein. During denaturation secondary and tertiary structures are destroyed but
primary structure remains intact. The coagulation of egg white on boiling is a common example of denaturation.
Another example is curding of milk which is caused due to the formation of lactic acid by the bacteria present in
milk. The reverse of denaturation is called renaturation.
Urea CO, + NH
(vi) Urease
Proteins> amino acids
vi) Pepsin
Proteins amino acids
(vii) Trypsin
(ix) Diastase Starch Maltose
Efficiency: Even a small amount of enzymes are highly efficient. This is because their molecules are regenerated
during their catalytic activity.
Those chemical substances which tend to reduce activity of a particular enzyme are called enzyme inhibitors.
VITAMINS
Vitamins are organic compounds which are essential for normal growth of life for animals, some bacteria and
micro organism. Vitamins not synthesized
are
through food. They are essential dietary factor.
by animals (except vitamin D). Vitamins are supplied to the organiem
Deficiency Diseases: Skin swelling around the mouth. Cracking of lips at the edges, bulging of eye
cells.
(c) Vitamin-B, : Niacin (Nicotinic Acid) and Nicotinamide
Natural Sources: Mushroom, Ground nut,
Bread etc.
Deficiency Disease: Pellagra
(d) Vitamin B,: Pantothenic
Natural Sources : Ground nut, Soyabean, Liver, Kidney
Deficiency Disease: Swelling in stomach and intestines
(e) Vitamin B: Pyridoxine
Natural Sources Yeast milk, Egg yolk, Cereals, Grams
Deficiency Disease: Convulsions
( Vitamin B12: Cyanocobalamine
Natural Sources: Meat, Fish, Egg, Curd, Milk etc.
Deficiency disease: Pernicious anemia, degradation of nervous system.
(9) Vitamin C:Ascrobic Acid
Natural source: Citrus fruits, Amla and Green leafy vegetables.
Deficiency disease: Scurvy, tooth decrease bleeding of gums.
(2) Fat Soluble Vitamins
(a) Vitamin-A: Retinol
Natural Sources Fish liver oil, Carrots, Butter and Milk
Natural Sources: Spinach and other green leafy vegetables, tomato, potato, cabbage, edible oil, liver
etc.
Enzyme, Nuclease
Nucleic Acid Nucleotide
NH,
MgO in H,0/A
H,PO,+ Nucleoside
Ho
Sugar+Heterocyclic bases
Sugars: Two sugars present in nucleic acid are ribose and deoxyribose.
Ribose is present in RNA and deoxyribose in DNA.
These sugars are present in furanose form.
Bases These are derivatives of purine and pyrimidine.
1
N N3
Purine Pyrimidine
Purine Bases:
NH
HC
C=N NH
NC -N CH
N CN NH
H H
NH,
H H
HC NH
C N
HC N
HC
HC N
HC
N
H
O=o N
H
o
H
Uracil (U)
Thymine (T)
Cytosine (C)
5
5
Base O-P-0-H,C Base
HO- HC O-
/H H H/H
HH
OH OH
OH OH
Nucleoside Nucleotide
Base Base
O-P-0-CH,
O-P-0-CH,
O
Sugar
Sugar
Phosphodiester 3
linkage O
OH
O-P O
Base
5'CH,
|Base
O-P-0-CH, o
0 Sugar
Sugar 3
OH
OH 3'end of chain
chain is as shown below.
version of nucleic acid
A simplified
Base Base
Base
nfarmmation reaarding the sequence of nucleotides in the chain of a nucleic acid is called its primary structure.
Ncleic acids have a secondary structure also. Two nucleic acid chains are held together by hydrogen bonds
hehween pairs of bases. Adenine forms hydrogen bonds with thymine whereas cytosine forms hydrogen bonds
with guanine.
in secondany structure of RNA, helices are present which are only single stranded. Sometimes they fold back
on themselves to form a double helix sturcture.
5
GE
A=T-
T=A-
ET-
C=G-
G=CC
T=A-
C=G
T=
GEC
A=T-
T-A
A==T
-T=A-
-C=G
G=C
5 3'
Double strand helix structure for DNA
Example 5: The third component present alongwith deoxyribose and a base in DNA is
Solution Phosphoric acid.