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Nucleic Acid Chemistry

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CHEMISTRY OF

NUCLEIC ACID

DR MARIAM MUNEER
LECTURER BIOCHEMISTRY
NUCLEIC ACIDS:
Nucleic acids are non protein
nitrogenous substances made up of
monomeric units called nucleotides.
NUCLEOSIDE NUCLEOTIDE

DEFINITION Nucleoside is a nucleobase linked to a Nucleotide is a monomer of nucleic


pentose sugar molecule acids like DNA and RNA

CONTENTS A pentose sugar and a nitrogenous A nitrogenous base, pentose sugar


base and a phosphate group
Examples include adenosine, Examples include ATP, cAMP, GTP etc
EXAMPLES guanosine, cytidine, uridine,
thymidine
Nucleic acid

Nucleotides

Phosphoric acid Nucleosides

Sugar Purine Pyrimidine


Ribose or Guanine base Cytosine,
deoxyribose and uracil or
Adenine thymine
Types
There are two types of nucleic acids,

the ribonucleic acid (RNA)


the de oxyribo nucleic acid (DNA),

….which on hydrolysis yield the sugar ribose and


deoxyribose respectively.
HISTONES
Histones are a small family of closely related basic proteins in
chromatin.

TYPES OF HISTONES:
H1 HISTONES: Easily detectable. Least tightly bound and can be
removed by salt solution. Organizational unit of this soluble
chromatin is nucleosome.
Nucleosomes: Contain four types of histones.
H2A , H2B , H3 AND H4____called core histones.
TYPES OF HISTONES

LINKER HISTONES
H1 histone links to the linker DNA outside the octamer.H1 is
half as abundant as the other histones.

CORE HISTONES
H2A, H2B, H3 and H4 are the core histones and form the
protein core around which the nucleosomal DNA is
wrapped.All these are present in equal amounts.
FUNCTION:
This association of histone octamer with DNA protects the DNA
from digestion by a nuclease.
DEOXYRIBONUCLEIC
ACID(DNA)
 DNA - a polymer of deoxyribo nucleotides.
 Usually double stranded.
 And have double-helix structure.
 found in chromosomes, mitochondria and chloroplasts.
 Carries the genetic information.
 Bound to basic proteins called histones.
Levels of structure in Nucleic acids
Primary structure of nucleic acids is the order of bases in
the polynucleotide sequence.

Secondary structure is the 3-dimensional


conformation of the backbone.

Tertiary structure is specifically the super coiling of


the molecule.
STRUCTURE OF DEOXYRIBONUCLEIC ACID (DNA)
Primary Structure:
Nucleotides of each of the two strands are covalently linked
by 3’—5’ phosphodiester bonds.
Each such bond is formed by ester linkages of a single
phosphate residue with the 3’-OH of one nucleotide with the
C-5’-OH group of the next nucleotide.
This kind of bonding gives rise to a liner
polydeoxyribonucleotide strand with 2 free ends on both
sides.
The primary structure is the number and sequence of
different deoxyribonucleotides joined together by
phosphodiester linkages.
STRUCTURE OF DNA:
Secondary Structure:
This consists of a double stranded helix formed by two
polydeoxyribonucleotide strands around a central axis.

First proposed by Watson and Crick in 1953.

Each of the two strands is coiled about a central axis , usually a


right handed helix.

The two sugar phosphate backbones wind around the outside of


the bases like spiral staircase.

The phosphodiester bonds run in opposite directions therefore


the strands are called antiparallel.
Adenine base of one strand is hydrogen bonded to a
thymine in the opposite direction while guanine bonded to
a cytosine.

Two hydrogen bonds between adenine and thymine while


three between guanine and cytosine.
DNA BASES
CHARGAFF’S RULE
The ratio of the purine to pyrimidine bases in the DNA molecule is
always around 1.

GUANINE +ADENINE/THYMINE +CYTOSINE = 1


In DNA the glycosidic bonds between sugar and bases are not
directly opposite each other and two grooves of unequal
width form around the double helix.

The edge of the helix that measures more than 180˚ from
glycosidic bond to glycosidic bond is called the major groove
and if it is less than 180˚ it is called minor groove.
TYPES OF DNA
B-DNA:
Adjacent nucleotides in each chain are rotated by 34.6˚
relative to each other.
Double helix completes one turn approximately every 10.4
base pairs.
A-DNA:

When B-DNA crystals are dried or when salt content of the


crystal is lowered , the long thin B-DNA molecule becomes the
short stubby molecule called A-DNA.

The number of base pairs per turn is about 11.

It is not found under physiological conditions.

Z-DNA:

Longer and thinner than B-DNA. It has left handed helix.

One complete turn has 12 base pairs.


DENATURATION OF DNA
Two strands of DNA can separate or unwind during processes
such as DNA replication, RNA transcription and genetic
recombination.
Complete unwinding of the DNA is called Denaturation.
Denaturation occurs when hydrogen bonds between bases
break.

TEMPERATURE OF DNA:
The temperature at which the strands are half denatured is
called the melting temperature.
DNA RNA
DNA is a deoxyribonucleic acid. RNA is ribonucleic acid.
DNA consist of 2 helical strands RNA is single stranded
In addition to A, G, C, the fourth In addition to A, G, C, the fourth base is U—
base is T—Uracil absent Thymine absent

DNA is Present in nucleus RNA is present in whole of the cell in the


cytoplasm as well as in nucleus.

Pentose sugar is deoxyribose Pentose sugar is ribose

. DNA can form RNA by the RNA cannot give rise to DNA under normal
process of “transcription conditions, but it can under special
experimental conditions using reverse
transcriptase
RIBONUCLEIC ACID
• Usually single stranded but double stranded also present in
some viruses.
 There are also three main components
a) Phosphate Group
b) Sugar(Ribose)
c) And Nitrogenous base
The Nitrogenous Bases
 They are divided into two groups:
i. Purine
ii. Pyrimidine
 Purines
 Adenine
 Guanine
 Pyrimidine
 Cytosine
 Uracil
TYPES OF RNA :
Each type of RNA plays and independent and entirely
different role in protein formation.
There are four different types of RNA :

1 Messenger RNA
2 Ribosomal RNA
3 Transfer RNA
4 Micro RNA
Messenger
RNA:
Which carries the genetic code to
the cytoplasm for controlling the
type of protein formed.
(m-
Messenger RNA RNA)
• Comprises only 5% of the RNA in the cell
• Most heterogeneous in size and base sequence
• All members of the class function as messengers
carrying the information in a gene to the
protein synthesizing machinery

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 The 5’ terminal end is capped by 7-
methyl guanosine triphosphate cap.
 The cap is involved in the recognition
of mRNA by the translating machinery
 It stabilizes m RNA by protecting it from
5’ exonuclease
 The 3’end of most m-RNAs have a
polymer of Adenylate residues( 20-250)
 The tail prevents the attack by 3’
exonucleases
 Histones and interferons do not contain poly
A
tails
 On both 5’ and 3’ end there are non
coding sequences which are not translated
(NCS)
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Structural Characteristics
of m-RNA

5’ cap and 3’ tail impart stability to m RNA


by
protecting from specific exo nucleases.
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 RNA CODON

 The m- RNA molecules are formed with the


help of DNA template during the process of
transcription.
 The sequence of nucleotides in m RNA is
complementary to the sequence of
nucleotides on template DNA.
 The sequence carried on m -RNA is read in
the form of codons.
 A codon is made up of 3 nucleotide bases

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Transfer RNA:

Which transports activated amino


acids to the ribosomes to be used
in assembling the protein
molecules.
Transfer RNA-The Anticodon:
Small RNA molecule
Clover leaf appearance
Transfers amino acids to protein molecule
Contains 80 nucleotides
Each tRNA recognizes specific codon on
mRNA.
Amino acid
accepter arm

Ribosome
binding site
Recognizes
specific enzyme
Anticodon:
The specific code in the tRNA
that allows it to recognize a
specific codon is a triplet of
nucleotides bases and is called
an anticodon.
Anticodon bases
combine loosely by
hydrogen bonding
with the codon bases
of mRNA.
Functions:
Works as carrier of amino acids
Participates in protein
synthesis (Translation).
Ribosomal
RNA:

Forms 80% of the total cellular RNA.


Which, along with about 75 different
proteins, forms ribosomes, the
physical and chemical structures on
which protein molecules are actually
assembled.
As the rRNA forms it collects in the nucleolus.
In nucleolus it binds with ribosomal proteins to form
granular condensation products that are predominant
subunits of ribosomes.
Subunits release from nucleolus and transported through
nuclear pores to almost all parts of cytoplasm.
In cytoplasm rRNA assembled to form mature, functional
ribosomes.
Function :
Ribosomal RNA maintains ribosomal assembly.
It also helps in binding mRNA to ribosomes.

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