Purine ,pyrimidine,

nucleoside, nucleotides,
structure of DNA

Submitted to - Mrs harpreet kaur

Submiited by - vanita garg
Class- Msc biotechnolgy
ROll no - 18011010
 CONTENTS…
 HISTORY OF NUCLEIC ACID
 COMPONENTS OF NUCLEIC ACID
 NUCLEOSIDE
 NUCLEOTIDE
 WATSONS AND CRICK MODEL
 TYPES OF DNA
INTRODUCTION…
• Frederic Miesher in 1869, isolated an acidic compound from the nuclear
material of salmon sperms, and named it as NUCLIEN which is now
called NUCLEIC ACID.
• Fischer in 1880, discovered purine and pyrimidine bases in nucleic acid.
• Nucleic acid are the macromolecule, the main information carrying
molecule of the cell and by, directing the process of protein synthesis,
they determine the inherited characteristics of every living being.
• Central Dogma: DNA RNA PROTEINS
 NUCLEIC ACIDS…
 Jones in 1920,proved the fact there are two types of nucleic acid:
1. Deoxyribonucleic acid (DNA)
2. Ribonucleic acid (RNA)
 Nucleic acid are present in plants and animals and viruses also contain
either RNA and DNA.
 DNA is found mainly in the chromatin of the cell nucleus and extranuclear
DNA also exists in mitochondria and chloroplasts where as most of the
RNA(90%) Is present in the cytoplasm and a little(10%) in the nucleous.
 The nucleic acids have 3 characteristic components:
1. A pentose sugar
2. Nitrogenous bases
3. Phosphoric group
1. PHOSPHORIC ACID…
 Molecular formula is H3PO4.
 It contains 3 monovalent hydroxyl group and
a divalent oxygen atom, all linked to
pentavalent phosphate atom.
2. PENTOSE SUGAR…
 The nucleic acid have two kinds of pentose sugar.
1. The deoxyribonucleotide units of DNA contain 2’ deoxy-D-ribose.
2. The ribonucleotide units of RNA contain D-ribose.
 These sugars in nucleic acids are present in the furanose form and are of
β- configuration.
 The pentoses form esters with phosphoric acid

ESTER BOND

.
 In this the OH groupsof the pentose,
especially those at C3 and C5, are
Involved forming a 3’,5’-phosphodiester
bond between adjacent pentose residues.
3’,5’-
phosphodiester
bond
3.NITROGENOUS BASES…
• All nucleic acids have 2 types of nitrogenous bases:
1. PURINES : It is a heterocyclic aromatic organic compound.
• It contains a six- membered pyrimidine ring
fused to the five- membered imidazole ring. Imidazole
eg: Adenine, guanine. ring
Pyrimidine
ring
2. PYRIMIDINES: It is a heterocyclic compound which contains a six-
membered
Ring with two nitrogen atoms and three double bonds.
• The base of a nucleotide is joined covalently
(at N-1 of pyrimidines and N-9 of purines) in
an N-β-glycosyl bond to the1’carbon of the
pentose and the phosphate is esterified to
the 5’ carbon. The N-β-glycosyl bond is
formed by removal of the elements of
water(a hydroxyl group from the pentose
hydrogen from the base).

β-glycosidic
ESTER linkage
BONDING
NUCLEOSIDES…
 Nucleosides are compounds in which nitrogenous bases are conjugated to
the pentose sugars by a β-glycosidic linkage.
 The β-glycosidic linkages involves the C-1’ of sugars and the hydrogen
atom of N-9(purines) or N-1(Pyrimidine),thus eliminating a molecule of
water.
 Nucleosides containing ribose are called ribonucleosides (also called
riboside) , while those possessing deoxyribose as
deoxyribonucleoside(also called deoxyribose).
BASE RIBONUCLEOSIDE DEOXYRIBONUCLEOS
IDE

ADENINE Adenosine Deoxyadenosine

GUANINE Guanosine Deoxyguanosine

CYTOSINE Cytidine Deoxycytidine

THYMINE Thymidine Deoxythymidine

URACIL Uridine Deoxyuridine

NUCLEOSIDE ANALOGUES AS DRUGS:
 Two nucleoside analogues :3’-azidodeoxythymidine(AZT) and 2’,3’-
dideoxycytidine(DDC),used for the treatment of acquires immune
deficiency syndrome(AIDS) patients. Human immunodeficiency
virus(HIV),is a RNA virus which requires a specific enzyme ,an RNA-
dependent DNA polymerase for replication.
 The AZT and DDC given to a AIDS patients , it is converted into
triphosphate forms , which can then compete with dTTP and dCTP ,
respectively as substrates for DNA synthesis. Which prevents continuous
elongation of the DNA molecule being synthesized.
NUCLEOTIDES…
 Nucleotides are the phosphoric acid esters of nucleosides.
 Phosphorylation is possible only at three positions (C’2, C’3,C’5) since C’1
and C’4 are involved in the furanose ring formation. In the deoxyribose of
a 2’-deoxyribonucleoside, so only two positions are available for
phosphorylation.

NUCLEOSIDE

NUCLEOTIDE
Functions of Nucleotides:
1. As carriers of chemical energy: Nucleotides may have one , two, or three
phosphate groups(NMPs, NDPs and NTPs) covalently linked at 5’-OH of
ribose . NTPs are used as a source of chemical energy to drive many
biochemical reactions.
 The hydrolysis of NTPs is an exergonic reactions
2. As components of enzyme factors : Many enzymes cofactors and coenzymes
contain adenosine as part of their structure(example: coenzyme A, FAD). In these
cofactors, adenosine does not participate directly, but removal of adenosine from
these cofactors usually results in drastic reduction of their activities.

3. As chemical messenger: The cells respond to their environment by some

hormones and chemical signals in the surrounding medium. The interaction of
these chemicals signals (first messengers) with receptors on the cell surface
often leads to the formation of second messengers inside the cell , which in turn
lead to adaptive changes inside the cell.
 The second messenger is a nucleotide. example : adenosine 3’,5’- cyclic
monophosphate(cyclic AMP).
DEOXYRIBONUCLEIC ACID…
HISTORY:
 William Astbury (1938) detected a periodicity of 3.4 angstroms.
 Rosalind franklin (1952) performed x- ray diffraction analysis of DNA crystal.
 Franklin and Wilkins (1950-1953) confirmed 3.4 periodicity
and noted uniform diameter of 20 angstrom(2nm).

The images of DNA taken by Franklin gave clue to Watsons

and crick about the width of double helix and spacing
of N- bases.

 Watsons and Crick(1953) proposed the DNA double helical model based on
Franklin’s X-ray crystallography analysis and other evidences.
WATSON AND CRICK MODEL…
 Proposed a double helix model of DNA ,received a noble prize in 1962.
Salient feature(commonly found DNA: B DNA)::
1. It consist of two helical polynucleotide chains, coiled around a common axis in the
form of a right handed double helix.
2. There are 2 interchain spacing or grooves:
a. Major groove(width:12 angstrom , depth :8.5 angstrom).
b. Minor groove(width:6 angstrom , depth: 7.5angstrom)
3. The two helices wind along the molecule parallel to the phosphodiester backbones.
4. The two chains run in opposite direction i.e. they are antiparallel . They are not
identical but their base pairing are complementary to each other.
5. The phosphate and deoxyribose units are found on the periphery of the helix ,
whereas the purines and pyrimidine bases occur in the center(bases are
perpendicular to the helix axis).
 20 6. The diameter of the helix is 20 angstrom . The
angstrom bases are 3.4angstrom apart along the helix axis
and rotation of 36 degrees . The helix contains 10
nucleotides residues.
MINOR GROOVE 7. The two chains are held together by hydrogen
bonds between the base pairs. Adenine always
MAJOR GROOVE pairs with thymine by 2 hydrogen bonds and
guanine with cytosine with 3 hydrogen bonds(base
complementary).

34 nm
 CHARGAFF’S RULE: (1950)

1. Sum of purines(A + G)= sum of pyrimidines(T + C)

2. Ratio of A/T and G/C is 1.
3. Ratio of A+T/G+C known as dissymmetry ratio, varies from one species to
the other species.
a. When the ratio exceeds one, such a DNA is called AT type.
b. When the ratio is less then one , such a DNA is called GC type.
 TYPES OF DNA:
CHARACTERISTIC A-DNA B- DNA C-DNA Z-DNA
S

SHAPE Broadest Intermediate Narrow Narrowest

HELIX SENSE Right handed Right handed Right handed Left handed

HELIX DIAMETER 25.5 23.7 19 18.4

RISE PER BASE 2.3 3.4 3.32 3.8

PAIR
BASE PAIRS PER 11 10 9.33 12
TURN

HELIX PITCH 25.30 35.36 30.97 45.60

 REFERENCES…
 FUNDAMENTAL OF BIOCHEMISTRY – S. CHAND.
 Principle of Biochemistry- LEHINGER.
 www.biology.com
THANKU…