THE NUCLEIC ACIDS

© 2016 Paul Billiet ODWS

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

© 2016 Paul Billiet ODWS

Two types of nucleic acid are found
• Deoxyribonucleic acid (DNA)

• Ribonucleic acid (RNA)

© 2016 Paul Billiet ODWS

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

© 2016 Paul Billiet ODWS

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
© 2016 Paul Billiet ODWS
 P
NUCLEIC ACID STRUCTURE G

P
• Nucleic acids are
C
polynucleotides
P
C
• Their building blocks are
nucleotides P
A

P
T

© 2016 Paul Billiet ODWS

P
T
 P
G
NUCLEOTIDE STRUCTURE
P
PHOSPHATE C

SUGAR P
C
Ribose or
Deoxyribose
P
A
BASE
PURINES PYRIMIDINES
P
Adenine (A) Cytocine (C)
T
Guanine(G) Thymine (T)
Uracil (U)
P
T
Types of nucleotides
Deoxyribose or Ribose is a pentose
P
G
C5

O P
C

C4 C1
P
C

C3 C2 P
A

© 2016 Paul Billiet ODWS P

T
 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
© 2016 Paul Billiet ODWS
 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

© 2016 Paul Billiet ODWS

 P
G

ADDING IN THE BASES P

C

• The bases are attached to P

the 1st Carbon C

• Their order is important

P
It determines the genetic A
information of the molecule
P
T

P
© 2016 Paul Billiet ODWS 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
© 2016 Paul Billiet ODWS T A
P
 Hydro
P
DNA IS MADE OF TWO STRANDS OF G C
POLYNUCLEOTIDE
P
• The sister strands of the DNA molecule run C G
in opposite directions (antiparallel)
P
• They are joined by the bases
C G
• Each base is paired with a specific partner:
A is always paired with T P
G is always paired with C A T

Purine with Pyrimidine

P
• Thus the sister strands are complementary T A
but not identical
• The bases are joined by hydrogen bonds, P
individually weak but collectively strong. T A
© 2016 Paul Billiet ODWS
 Purines & Pyrimidines

Adenine Thymine

Guanine Cytosine
© 2016 Paul Billiet ODWS
Structure of nucleotides P
G

P
C

P
C

P
A

P
T

P
Nucleotide Structure - 4
Base-Sugar-PO42-
4
3 5N

2 6
1
N
5’
C O
4’ 1’

3’ 2’

OH

Nucleoside
Nucleotide Structure - 4
Base-Sugar-PO42-
4
3 5N

2 6
O 1
N
5’
O P O C O
O 4’ 1’

3’ 2’

OH

Nucleoside Monophosphate
 N NH2 O O N NH2
O O O
O P O P O P O O N H2O O P O P O O N
N
O O
N + HPO4 2- + ~31 KJ/mol
O O O N
N (7.4 Kcal/mol)
HO OH HO OH
ATP ADP
Nucleoside, nucleotides and nucleic acids
phosphate

sugar base

phosphate phosphate

sugar base
sugar base sugar base

phosphate
nucleoside nucleotides
sugar base

nucleic acids

The chemical linkage between monomer units in nucleic acids

is a phosphodiester 20
Deoxyribonucleotides of nucleic acids
 Nucleic Acid Structure
Polymerization

P P P P P P
N N
C C
S Phosphodiesterase S

P
+ P P
N
C
(PPi)
S
P P P
N
C
S
Formation of polynucleotide
Nucleic Acid Structure
The double helix

Minor
Groove

Major
Groove
 Physical Structure (cont’d)
 Chains are anti-parallel (i.e in opposite
directions)
 Diameter and periodicity are consistent
 2.0 nm
 10 bases/ turn
 3.4 nm/ turn
 Width consistent because of
pyrimidine/purine pairing
Wilkins & Franklin (1952): X-ray crystallography

kentsimmons.uwinnipeg.ca/cm1504/Image265.gif
© 2016 Paul Billiet ODWS
Erwin Chargaff’s Data (1950-51)

© 2016 Paul Billiet ODWS

Watson & Crick Base pairing

© 2016 Paul Billiet ODWS

The Double Helix (1953)

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