Asam Nukleat

THE NUCLEIC ACIDS
Friedrich Miescher in 1869
• Isolated what he called

nuclein from the nuclei of
pus cells
• Nuclein was shown to
have acidic properties,
hence it became called
nucleic acid
Two types of nucleic acid are found
• Deoxyribonucleic acid (DNA)
• Ribonucleic acid (RNA)

The distribution of nucleic acids in the
eukaryotic cell
• DNA is found in the nucleus
with small amounts in mitochondria and
chloroplasts
• RNA is found throughout the cell
DNA as genetic material: The
circumstantial evidence
1. Present in all cells and virtually restricted to the
nucleus
2. The amount of DNA in somatic cells (body cells) of any
given species is constant (like the number of
chromosomes)
3. The DNA content of gametes (sex cells) is half that of
somatic cells.
In cases of polyploidy (multiple sets of chromosomes)
the DNA content increases by a proportional factor
4. The mutagenic effect of UV light peaks at 253.7nm.
The peak for the absorption of UV light by DNA
NUCLEIC ACID STRUCTURE
• Nucleic acids are polynucleotides
• Their building blocks are nucleotides

NUCLEOTIDE STRUCTURE
PHOSPHATE SUGAR BASE

PURINES PYRIMIDINES
Ribose or
Deoxyribose Adenine (A) Cytocine (C)
Guanine(G) Thymine (T)
Uracil (U)
NUCLEOTIDE
Chemical Structure of DNA vs RNA
Ribonucleotides have a 2’-OH
Deoxyribonucleotides have a 2’-H
Pentose Sugars
• There are two related pentose sugars:
- RNA contains ribose
- DNA contains deoxyribose
• The sugars have their carbon atoms numbered with
primes to distinguish them from the nitrogen bases
DNA RNA
CH2 o CH2 o
H H
H H H
H H
H H
OH
Deoxyribose Ribose
sugar (O on C2 sugar (no
is missed) missed O)
Deoxiribo-Nucleic-Acid Ribo-Nucleic-Acid
Double stranded nucleic acid Single stranded nucleic acid
Bases: A, G, C, T Bases: A, G, C, U
Ribose is a pentose
C5
C4 C1
C3 C2
Spot the difference
RIBOSE DEOXYRIBOSE
CH2OH CH2OH
O OH O OH
C C C C
H H H H H H H H
C C C C
OH OH OH H
P
THE SUGAR-PHOSPHATE
BACKBONE P
• The nucleotides are all

orientated in the same P
direction
P
• The phosphate group joins
the 3rd Carbon of one sugar
to the 5th Carbon of the next P
in line.
P
P
G
ADDING IN THE BASES P

C
• The bases are attached to

P
1st
the Carbon C
• Their order is important
P
It determines the genetic
A
information of the molecule
P
T
P
T
Hydrogen bonds
P
G C
DNA IS MADE OF P
P
TWO STRANDS OF C G
POLYNUCLEOTIDE P
P
C G
P
P
A T
P
P
T A
P
P
T A
P
DNA IS MADE OF TWO STRANDS OF
POLYNUCLEOTIDE
• The sister strands of the DNA molecule run in
opposite directions (antiparallel)
• They are joined by the bases
• Each base is paired with a specific partner:
A is always paired with T
G is always paired with C
Purine with Pyrimidine
• Thus the sister strands are complementary but not
identical
• The bases are joined by hydrogen bonds,
individually weak but collectively strong.
Nucleic Acid Structure
“Base Pairing”
DNA base-pairing is antiparallel
i.e. 5’ - 3’ (l-r) on top : 5’ - 3’ (r-l) on
5’ 3’
T A G C A C
A T C G T G
3’ 5’
Erwin Chargaff’s Data (1950-51)
© 2016 Paul Billiet ODWS

Wilkins & Franklin (1952): X-ray crystallography
kentsimmons.uwinnipeg.ca/cm1504/Image265.gif
Purines & Pyrimidines
Adenine Thymine
Guanine Cytosine
Watson & Crick Base pairing

Based on McMurry, Organic Chemistry, Chapter 28, 6th
edition, (c) 2003
23
Purine and Pyrimidine

• Pyrimidine contains two pyridine-like nitrogens in a six-
membered aromatic ring
• Purine has 4 N’s in a fused-ring structure. Three are
basic like pyridine-like and one is like that in pyrrole
Nucleotide Structure - 2
Bases - Purines
NH2
Adenine N
N
A
N
N
N 6 H
7 5 1N
8
9 4 2 O
3
N N N
NH
G
Guanine N N NH2
H
Bases - Pyrimidines
O
H 3C
Thymine NH
T
N O
4
3 5 N H
2 6 NH2
1
N
N
C
Cytosine N O
H
Nitrogen Bases
• The nitrogen bases in nucleotides consist of two general types:
- purines: adenine (A) and guanine (G)
- pyrimidines: cytosine (C), thymine (T) and Uracil (U)
Bases - Pyrimidines
Thymine is found ONLY in DNA.
In RNA, thymine is replaced by uracil
Uracil and Thymine are structurally similar
Uracil O
4
3 5 N NH
2 6
U
1
N N O
H
Names of Nucleosides and Nucleotides
The Double Helix (1953)
© 2016 Paul Billiet ODWS www.chem.ucsb.edu/.../images/WatsonCrick.jpg

Nucleic Acid Function
DNA
Genetic material - sequence of nucleotides encodes different
amino acids
RNA
Involved in the transcription/translation of genetic material
(DNA)
Genetic material of some

viruses

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THE NUCLEIC ACIDS

Friedrich Miescher in 1869

• Isolated what he called

• Ribonucleic acid (RNA)

• Their building blocks are nucleotides

PHOSPHATE SUGAR BASE

Double stranded nucleic acid Single stranded nucleic acid

• The nucleotides are all

ADDING IN THE BASES P

• The bases are attached to

© 2016 Paul Billiet ODWS

© 2016 Paul Billiet ODWS

Purine and Pyrimidine

© 2016 Paul Billiet ODWS www.chem.ucsb.edu/.../images/WatsonCrick.jpg

Genetic material of some

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