Chapter - Biomolecules

Introduction

u A biomolecule is a chemical compound found in living organisms. It is a

building block of a living organism .

u Definition: Complex organic compounds which make living matter and are
responsible for the growth and maintenance of living organisms are called
biomolecules.
 1. Carbohydrates

u Carbohydrates are mainly produced by plants. They are also known as

saccharides due to its sweet taste .
u Sugar, glucose, fructose, starch, cellulose etc. are important carbohydrates.
u Carbohydrates are the organic compounds made up of C,H & O.
u General formula of most of the carbohydrates is Cx(H20)y [ old concept ]
u Definition : Carbohydrates are optically active polyhydroxy aldehydes or
polyhydroxy ketones or compounds which give these on hydrolysis.
Classification of Carbohydrates

1. Classification on the basis of physical properties.

u Sugars: They are colourless, crystalline solids, sweet in taste, soluble in
water and have sharp melting point e.g. glucose, fructose, sucrose, maltose
etc.
u Non-sugars: They are colourless, tasteless, amorphous solids, sparingly
soluble in water, e.g., starch, cellulose, dextrin, glycogen etc. They do not
have sharp melting point.
2. Classification on the Basis of Hydrolysis
u Monosaccharides: They are the simplest
carbohydrates and do not get hydrolysed, e.g.,
glucose, fructose, ribose etc.
u Monosaccharides which contain -CHO group are
called aldoses & which contains ketonic group are
called ketoses.
u Oligosaccharides: They get hydrolysed and give 2 to 10 monosaccharide molecules.
u These arms further classified as disaccharides, trisaccharides etc.
u (1) Disaccharides: They on hydrolysis give two units of monosaccharides. Sucrose, maltose and
lactose are all disaccharides. Their molecular formula C12H22011 is same.
u But their structures are different and on hydrolysis they give different monosaccharide units.

u Trisaccharides: They on hydrolysis give 3 molecules of monosaccharides.

u Polysaccharides: They on hydrolysis give large number of monosaccharide molecules, e. g.,
starch, cellulose, sum etc. Their molecular formula (C6H10O5)n is same.
3. Classification on the Basis of Reducing Properties

u Carbohydrates which reduce Tollens’ reagent and Fehling’s solution are

called reducing carbohydrates, eg, glucose, fructose, ribose, maltose,
lactose etc. They have free reducing groups such as aldehydic or ketonic
group.
u Non-reducing carbohydrates do not reduce Tollens' reagent and
Fehling's solution, e.g., sucrose, starch, cellulose etc. They do not have
free reducing groups.
 Some Important monosaccharides
u Glucose occurs in nature in free state as well as in combined state. It is present in
sweet fruits and honey. Ripe grapes contain 20% glucose.
Preparation of Glucose
1. From sucrose (Cane sugar) : Cane sugar is boiled with dil. HCI or dil. H2SO4 in
alcoholic solution. Sugar gets hydrolysed to give equal amounts of glucose and fructose.

2. From starch: Glucose is prepared on large scale by the hydrolysis of starch. Starch is
boiled with dil. H2SO4 at 393 K under pressure (2-3 bar).
Physical Properties
u Glucose is a white crystalline solid (m.p. 419 K), sweet in taste. It is soluble
in water but sparingly soluble in alcohol. It is optically active.
Chemical Properties:
u Glucose has one -CHO group, 5 -OH groups and the 6 C-atoms are
present in a straight chain. Out of 5 -OH groups, one -OH group is primary
(- CH,OH) and 4 -OH groups are secondary (CHOH-). Glucose gives the
reactions of -OH and -CHO groups. Its structure is : OHC- (CHOH)4-
CH,OH.
1. Acetylation: With acetic anhydride, glucose gives pentaacetate derivative. This shows that
glucose contains 5 -OH groups.

2. Reaction with hydroxylamine (NH2OH) : Glucose condenses with hydroxylamine to form

glucoxime. This shows that glucose contains one carbonyl group (aldehydic or ketonic).
3. Reaction with hydrogen cyanide (HCN) : An addition product glucose
cyanohydrin is formed.

u This reaction also shows that glucose contains one carbonyl group (aldehyde or
ketonic).
4. Reduction of Tollens' reagent : Glucose solution reduces Tollens' reagent
(ammoniacal silver nitrate solution). Silver mirror is formed.
5. Reduction of Fehling's solution : Glucose solution is boiled with Fehling's solution. Reddish brown
ppts. of cuprous oxide are formed. Reactions (4) and (5) confirm that glucose contains -CHO group.

6. Oxidation: On oxidation with HNO3, glucose gives a dicarboxylic acid (saccharic acid). Primary
alcoholic group (- CH2OH) and aldehydic group (- CHO) get oxidised into -COOH group. These reactions
show that glucose contains a primary alcoholic group (- CHzOH) as well as -CHO group.
u On oxidation with mild oxidising agent such as bromine water, gluconic
acid is formed. Only - CHO group ge oxidised to -COOH group.
7. Reaction with Hl: On prolonged heating with hydrogen iodide, glucose gives n-hexane.

Formation of -hexane shows that the 6 C-atoms in glucose are present in a straight chain.
8. Reaction with phenylhydrazine (NH2NHC6H5) : With small amount of the reagent, glucose
phenylhydrazone is formed.
Structure of Glucose
 Evidence of Structure of Glucose
u Glucose is an aldohexose and is also known as dextrose. It is a monomer of starch and cellulose.
Its structure is derived from the following facts:
1. Molecular formula: Its molecular formula is C6H1206.
2. Presence of straight carbon chain: On heating with HI, glucose gives n-hexane suggesting that all
the 6C-atoms are present in a straight chain.
3. Presence of carbonyl group : shown in rxn 2,3
4. Presence of aldehydes group : shown in rxn 6
5. Presence of 5 OH group : shown in rxn 1
6. Presence of 1 primary alcoholic group : shown in rxn 6
7. Open chain structure .
Structure of glucose :

1. Open chain structure

Fisher Projection
u 'D' and ‘L’ notations : For this purpose glyceraldehyde, which contains one
asymmetric carbon atom, has been chosen as the standard. It exists in two
enantiomeric forms.
u For assigning configuration of monosaccharides, lowest asymmetric carbon atom
is compared
u The -OH group lies on right hand side in the structure —> D-Glyceraldehyde
u The -OH group lies on left hand side in the structure —> L-Glyceraldehyde
 Objections Against Straight Chain
Structure of Glucose
1. Glucose contains -CHO group, even then it does not react with NaHSO; or Schiff's reagent.
2. Glucose exists in two stereoisomeric forms: α –D-glucose and β–D-glucose.
3. The α -form of glucose Melting point 419 K Obtained by crystallisation from concentrated
solution of glucose at 303 K whereas The β-form of glucose Melting point is 423
K Obtained by crystallisation from hot and saturated aqueous solution at 371 K
4. Glucose reads with hydroxylamine whereas pentacetate of glucose does not react with
hydroxylamine This; that -CHO group is absent in glucose pentaacetate.
Cyclic Structure of Glucose
u Glucose forms a six-membered ring in which -OH at C-5 is involved in ring formation . It is
called pyranose structure
u The C1 carbon is anomeric carbon. The a - and B -forms are called anomers. The six
membered cyclic structure of glucose is pyranose structure. It is in analogy with the
organic compound pyran which has 5 C- and one O-atom in the ring
Haworth Structure
Mutarotation

u The change in specific rotation of the solution of an optically active

compound without any change in other properties is called mutarotation.
Fructose

u Fructose occurs in honey and sweet fruits.

u Molecular formula of fructose is C6H1206
u Fructose is a ketohexose
Structure of Fructose
Open chain structure Cyclic structure

u Open chain structure-

Haworth Structure

u Fructose also exists in furanose structure in which S-membered ring is

formed between C2 and C4 through O-atom.
 Proteins

u Proteins are the Most abundant biomolecules of the living

system
u It is Required for growth and maintenance of body
u The word protein is Derived from Greek word, "proteios"
which means prime importance
u All proteins are polymers of α-amino acids
u Amino acids contain amino (-NH2) and carboxyl (-COOH)
functional groups
u Amino acids are classified as α , β , γ , δ amino acids depending
upon the position of (-NH2) group with respect to the (-COOH)
Nomenclature of Amino Acids
u Glycine u Tyrosine
Greek glykos means sweet Greek, tyros means cheese
Symbol of
Amino acids -
 Classification of Amino Acids
1. Amino acids are classified as acidic, basic of neutral depending upon the relative number of
amino and carboxylic group in the amino acid molecule.
u If the number of – NH2 and - COOH groups is equal, the amino acid is neutral .
u If the number of – NH2, group is more than -COOH groups, the amino acid is basic .
u If the number of -COOH groups more than NH2 groups, the amino acid is acidic.
2. Essential & Non Essential Amino Acids :
u Those amino acids which can be synthesised in the body are known as non-essential
amino acids, e.g., glycine , alanine etc.
u Those amino acids which cannot be synthesised in the body are known as essential amino
acids. These are 10 in number, e.g., valine, leucine, isoleucine etc.
Properties of Amino Acids:

u Amino Acids are Usually colourless, crystalline solids

u They have high melting solids and are Water-soluble
u They Behaves like salts rather than simple amines or carboxylic acids
u They show amphoteric behaviour in Zwitter ion form
u In aqueous solution, the carboxyl group looses a proton and amino group
gains the proton giving rise to dipolar ion known as ZWITTER ION.
u Except Glycine all the amino acids are optically active
Structure of Proteins
u Proteins on hydrolysis give a -amino acids. This shows that proteins are made up of a -amino
acid molecules.
u Amino acids are linked to each other by peptide bond or peptide linkage ( —CONH —).

u The product is known as Dipeptide because it is made from two amine group .
u Types of Peptide – 1. Dipeptide 2. Tripeptide 3. Polypeptide
u A polypeptide with more than hundred amino acid residues, having molecular mass higher
than 10,000u is called a protein
 Classification of Proteins

u On the basis of their molecular shape, proteins are classified

into two types :
1. Fibrous proteins: In these proteins, the polypeptide chains
run parallel and are held together by hydrogen bonds and
disulphide (-S-S-) bonds. They have fibre like structure. Such
proteins are generally insoluble in water. E.g. Keratin , Myosin
2. Globular proteins: In these proteins, molecules are folded
forming compact units which acquire spherical shape.
Intermolecular forces in these Proteins Are comparatively
weak. These are soluble in water, e.g., albumin, insulin,
haemoglobin etc.
Structure of Proteins

1. Primary Structure of Proteins

u Primary structure of proteins describes the sequence of amino
acids in a protein molecule. It describes the disulphide bridges (-S
-S-), if present.
2. Secondary Structure of Proteins
u I t describes : About the manner in which the different polypeptide
chains are folded.
u About the nature of the bonds which stabilise protein structure.
u About the conformation which the polypeptide chains assume as
a result of hydrogen bonding.
Types of secondary structure

1. Alpha -Helix structure: This type of structure is

acquired when R-groups in amino acids are large.
2. Beta - pleated sheet structure : X-ray studies show
that polypeptide chains lie side by side in a zig-zag
manner.
u The chains are held together by intermolecular
hydrogen bonds. Two types of pleated sheets are
possible- -parallel and antiparallel. In parallel structure,
all the chains run in the same direction. In antiparallel
structure, chains run alternately in opposite direction.
3. Tertiary Structure
u Tertiary structure gives the overall shape of protein
molecule. The three dimensional structure developed
due to the folding, coiling and bending of polypeptide
chains is called tertiary structure of proteins.
u Globular proteins have three dimensional tertiary
structure.
4. Quaternary Structure
u Some of the proteins are composed of two or more
polypeptide chains. These chains are called sub-units.
These sub-units may be identical or different. The
quaternary structure describes the spatial arrangement
of the sub-units with respect of each other.
Native State of Proteins and their
Denaturation

u The energetically most stable shape of the

protein at normal pH and temperature is
called its native state.
u Denaturation of Proteins - The process which
changes the physical and biological
properties of a protein without changing its
composition is called denaturation.
Functions of Proteins

1. Transport Agents
2. Structural Materials
3. Enzymes
4. Metabolic Process
5. Antibodies
Enzymes

u Enzymes are nitrogen containing complex organ compounds.

u Enzymes make the reactions very fast in plants an animals at ordinary temperature and pH.
u Enzymes are biocatalyst.
Nomenclature
u They are generally named after the compound or class of compounds upon which they work
The enzyme that catalyses hydrolysis of maltose is named as maltase.
u Sometimes enzymes are also named on the type of reaction being catalysed. For example,
the enzymes which catalyse the oxidation of one substrate with simultaneous reduction of
another substrate are named as oxidoreductase.
u Similarly, the enzymes which catalvse the hydrolysis of substrate are called hydrolase.
Vitamins

u Vitamins are a group of organic compounds which are required in very

small amounts for the healthy growth and functioning of animal organisms.
 Classifications of Vitamins

u Vitamins are classified in two groups depending upon their solubility

in water or fat.

1. Fat Soluble Vitamins - They are oily substances not readily soluble
in water. They are soluble in oils and fats. This group of vitamins
includes vitamins A, D, E and K.

2. Water Soluble Vitamins - This group of vitamins includes vitamins

of group p (B-complex), vitamin C, etc. The water soluble vitamins
as stored in much lesser amounts in the cells.
NUCLEIC ACIDS
u Every generation of every species resembles its ancestors in many ways.
u There are two types of nucleic acids : (i) DNA (deoxyribonucleic acid) (i) RNA (ribonucleic acid).
Composition of NUCLEIC ACID :
1. Pentose sugar
2. A nitrogen containing heterocyclic base.
3. Phosphoric acid
u DNA consist of 4 bases :-
1. Adenine
2. Guanine
3. Cytosine
4. Thymine
u RNA consist of 4 bases :-
1. Adenine
2. Guanine
3. Cytosine
4. Uracil
Structure of Nucleic Acid
u Nucleoside : A unit formed by the attachment of a base to 1’ -position of sugar is
known as nucleoside

u Nucleotide: When nucleoside is linked to phosphoric acid at 5’-position of sugar

moiety, the unit obtained is called nucleotide .
Formation of Dinucleotide

u Nucleotides are joined together by

Phosphodiester linkage between 5' and 3'
carbon atoms of the pentose sugar

u Information regarding the sequence of

nucleotides in the chain of a nucleic acid is
called its primary structure
DNA, RNA : Secondary structure

u Watson and Crick gave a double strand helix

structure for DNA
u Adenine pairs with Thiamine only &
u Guanine pairs with Cytosine only
u Single stranded structure of RNA
u RNA molecules are of three type
u Messenger RNA (m-RNA)
u Transfer RNA (t-RNA)
u Ribosomal RNA (r-RNA)
Lipids & Hormones

u Lipids - Lipids are a large and diverse group of naturally occurring organic compounds that are
insoluble in water but are soluble in non-polar organic solvents.
Oils, fats, waxes, steroids, butter, fat soluble vitamins etc. are all lipids.
u Hormone - A hormone is a chemical released by g cell or a gland in one part of the body. It
then sends our messages that affect cells in other parts of the organism.
u Some important hormones :
1. Adrenaline
2. Insulin
3. Thyroxine
4. Pituitary hormones