Nucleic Acids
DNA & RNA
What do they do ?
•Dictate amino-acid sequence in
proteins
•Give information to chromosomes,
which is then passed from parent to
offspring
What are they ?
th
•The 4 type of
macromolecules
•The chemical link between
generations
•The source of genetic
information in chromosomes
The central dogma of molecular biology.
28.11 Nucleic Acids and Heredity
• Processes in the transfer of genetic information:
• Replication: identical copies of DNA are made
• Transcription: genetic messages are read and carried out of
the cell nucleus to the ribosomes, where protein synthesis
occurs.
• Translation: genetic messages are decoded to make
proteins.
Based on McMurry, Organic Chemistry, Chapter 28, 6th
5
edition, (c) 2003
The nucleus contains the cell’s DNA (genome)
RNA is synthesized in the nucleus and exported
to the cytoplasm
Nucleus
replication
Cytoplasm
DNA
transcription
RNA (mRNA)
translation
Proteins
Two types of Nucleotides
(depending on the sugar they contain)
1- Ribonucleic acids (RNA)
The pentose sugar is Ribose (has
a hydroxyl group in the 3rd
carbon---OH)
2- Deoxyribonucleic acids (DNA)
The pentose sugar is Deoxyribose
(has just an hydrogen in the same
place--- H) Deoxy = “minus
oxygen”
Definitions
Nucleic acids are polymers of nucleotides
Nucleotides are carbon ring structures containing nitrogen linked to a
5-carbon sugar (a ribose)
5-carbon sugar is either a ribose or a deoxy-ribose making the
nucleotide either a ribonucleotide or a deoxyribonucleotide
In eukaryotic cells nucleic acids are either:
Deoxyribose nucleic acids (DNA)
Ribose nucleic acids (RNA)
Messenger RNA (mRNA)
Transfer RNA (tRNA)
Ribosomal RNA (tRNA)
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
Nucleotide Structure
Despite the complexity and diversity of life the structure of DNA is
dependent on only 4 different nucleotides
Diversity is dependent on the nucleotide sequence
All nucleotides are 2 ring structures composed of:
5-carbon sugar : β-D-ribose (RNA)
β-D-deoxyribose (DNA)
Base Purine
Pyrimidine
Phosphate group A nucleotide WITHOUT a phosphate group is a
NUCLEOSIDE
NUCLEIC ACIDS (DNA and RNA) Notes
DNA – Deoxyribonucleic Acid
•DNA controls all living processes including
production of new cells – cell division
•DNA carries the genetic code – stores and
transmits genetic information from one
generation to the next
•Chromosomes are made of DNA
•DNA is located in the nucleus of the cell
Nucleotides and Nucleosides
• Nucleotide =
• Nitrogeneous base
• Pentose
• Phosphate
• Nucleoside =
• Nitrogeneous base
• Pentose
• Nucleobase =
• Nitrogeneous base
What are they made of ?
• Simple units called nucleotides, connected
in long chains
• Nucleotides have 3 parts:
1- 5-Carbon sugar (pentose)
2- Nitrogen containing base
(made of C, H and N)
3- A phosphate group ( P )
• The P groups make the links that unite the
sugars (hence a “sugar-phosphate
backbone”
Nucleic Acids
• Nucleic acids are molecules that store information for cellular
growth and reproduction
• There are two types of nucleic acids:
- deoxyribonucleic acid (DNA) and ribonucleic acid (RNA)
• These are polymers consisting of long chains of monomers
called nucleotides
• A nucleotide consists of a nitrogenous base, a pentose sugar
and a phosphate group:
Nucleic Acids
DNA and RNA are nucleic acids, long, thread-like polymers
made up of a linear array of monomers called nucleotides
All nucleotides contain three components:
1. A nitrogen heterocyclic base
2. A pentose sugar
3. A phosphate residue
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
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
Monophosphate
Nucleotide Function
Building blocks for DNA and RNA
Intracellular source of energy - Adenosine triphosphate (ATP)
Second messengers - Involved in intracellular signaling
(e.g. cyclic adenosine monophosphate [cAMP])
Intracellular signaling switches (e.g. G-proteins)
Nucleotide Structure - 4
Phosphate Groups
Phosphate groups are what makes a nucleoside a
nucleotide
Phosphate groups are essential for nucleotide
polymerization
Basic structure:
O P O X
O
Nucleotide Structure - 4
Phosphate Groups
Number of phosphate groups determines nomenclature
Monophosphate O
e.g. AMP
O P O CH2
Free = inorganic
phosphate (Pi) O
Diphosphate O O
e.g. ADP
O P O P O CH2
Free = Pyro-
O O
phosphate (PPi)
Nucleotide Structure - 4
Phosphate Groups
Triphosphate O O O
e.g. ATP
O P O P O P O CH2
No Free form exists O O
O
•It is the order of these base pairs that determines
genetic makeup
• One phosphate + one sugar + one base = one nucleotide
•Nucleotides are the building blocks of DNA –
thus, each strand of DNA is a string of nucleotides
Sanger dideoxy sequencing incorporates dideoxy
nucleotides, preventing further synthesis of the DNA strand
base（purine、pyrimdine）+ribose（deoxyribos
N-glycosyl linkage
nucleoside+phosphate
phosphoester linkage
nucleotide
phosphodiester linkage
nucleic acid
Nucleotide Structure - 1
Sugars
HOCH2 OH
O
Generic Ribose
Structure Ribose
5’
HOCH2
O OH OH
4’ 1’
3’ 2’
HOCH2 OH
O
N.B. Carbons are given numberings as a
prime
Deoxyribose
OH H
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
Based on McMurry, Organic Chemistry, Chapter 28, 6th
29
edition, (c) 2003
Nucleotide Structure - 2
Bases - Purines
NH2
Adenine N
N
A
N
N
N 6 H
7 5 1N
8
9 4
3
2 O
N N N
NH
G
Guanine N N NH2
H
Nucleotide Structure - 3
Bases - Pyrimidines
O
H3C
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)
Nucleotide Structure - 4
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
Nucleosides and Nucleotides
• A nucleoside consists of a nitrogen base linked by a glycosidic
bond to C1’ of a ribose or deoxyribose
• Nucleosides are named by changing the the nitrogen base
ending to -osine for purines and –idine for pyrimidines
• A nucleotide is a nucleoside that forms a phosphate ester with
the C5’ OH group of ribose or deoxyribose
• Nucleotides are named using the name of the nucleoside
followed by 5’-monophosphate
Names of Nucleosides and Nucleotides
AMP, ADP and ATP
• Additional phosphate groups can be added to the nucleoside
5’-monophosphates to form diphosphates and triphosphates
• ATP is the major energy source for cellular activity
