UNIVERSITY OF ZAMBIA
SCHOOL OF NATURAL SCIENCES
CHEMISTRY DEPARTMENT
NUCLEIC ACIDS
2020
What are nucleic acids?
Nucleic acids are polymers of nucleotides.
Nucleic acids store information for cellular growth and reproduction.
There are two types of nucleic acids namely:
Deoxyribonucleic acid (DNA) and ribonucleic acid (RNA).
Specific examples of nucleic acids includes
Ribosomal RNA (rRNA).
Messenger RNA (mRNA).
Transfer RNA (tRNA)
The nucleic acids DNA and RNA consist of monomers called nucleotides.
The nucleotides consist of three components namely:
a pentose sugar
nitrogen-containing base.
Phosphate.
What Pentose sugar do you find
in nucleic acids?
The pentose (five-carbon) sugar found in RNA is ribose.
While in DNA is deoxyribose with no O atom on carbon 2’.
Note that the carbon atoms in pentose sugars in nucleic acid are
numbered with primes to distinguish them from the atoms in nitrogen
bases thus.
What are nitrogenous bases?
Nitrogenous base are planar or almost planar heterocyclic
aromatic compound contain nitrogen as a heteroatom.
The Nitrogenous base found in nucleic acids are called purines and
pyrimidines.
Purines are nine membered heterocyclic nitrogenous base and
pyrimidines are six membered heterocyclic nitrogenous base.
Examples of pyrimidines includes:
Cytosine (C)
Guanine (G)
Thymine (T)
Uracil(U)
Examples of purines includes:
Guanine (G)
Adenine (A)
What are nitrogenous bases?
• The chemical structure of parent purines and pyrimidines
is given below.
• Note that the numbering of atoms in the ring in purines and
pyrimidines is different.
H 7
H C6 N
C4
1N 5 C
N 3 CH 8CH
5
2 HC2 3 4 C
HC 6CH N9
N
N H
1
Pyrimidine Purine
• The naturally occurring purines and pyrimidines are substituted.
• Most substituted pyrimidines are substituted on carbon 2 and carbon4
• A few are substituted at carbon 5.
• Most substituted purines are substituted on carbon 3 and carbon 6
5
What are specific examples of
nitrogenous base found
in nucleic acids?
(2-oxo-4-aminopyrimdine) 5-methyl-2,4 bis-oxo- pyrimidine
2,4 bis-oxo-pyrimidine
6-aminopurine (2-amino-6-oxo-purine)
What is a nitrogenous base?
O
C N
HN C
NH2 CH
C C
C H2N N N
N CH H
C CH
O N
H
Adenine Guanine
Purines
O O
C
C CH3
NH2 HN HN CH
C
C CH
C N C CH O N
N C O N H
CH H
HC C
N N Thymine (DNA) Uracil (RNA)
H
Cytosine Pyrimidines
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What is a minor base?
A modified major base is called minor base.
Both DNA and RNA contain minor bases.
In DNA most of these minor bases are methylated forms of major bases.
In some viral DNAs certain bases may be hydroxymethylated or
glycosylated.
Altered bases in DNA have roles in regulating and protecting the genetic
information.
Minor bases are also found in RNA especially tRNA.
What is the nomenclature of
minor bases?
When an atom on the ring is substituted the ring position
of the substituent is indicated by its number and the element to which
the substituent is attached is not indicated eg 5-methyguanosine.
When the substituent is attached to an exocyclic atom, the atom is
identified and the ring position to which its attached is denoted with a
superscript eg N6 methyladenosine.
Methylated heterocyclic bases of plants include the xanthine derivatives
Such as
caffeine of coffee,
theophylline of tea, and
theobromine of cocoa
What is a nucleoside?
The pentose sugars and nitrogenous base may combine in
condensation reaction to form a N-glycosidic linkage or bond.
In this combination the compound that is formed is called a glycoside
and is specifically called a nucleoside.
In the formation of a nucleoside usually a nitrogen of a base is linked by
a glycosidic bond to C1’ of a sugar either a ribose or deoxyribose.
Specifically N-1 of pyrimidines is linked by a glycosidic bond to C1’ of a
sugar either a ribose or deoxyribose and N-9 of purines is linked by a
glycosidic bond to C1’ of a sugar either a ribose or deoxyribose.
In both cases an N-β-glycosyl bond is formed.
When N-β-glycosyl bond is formed water is lost (a hydroxyl group from
the pentose and hydrogen from the base).
The name of the nucleoside is given by replacing ine in the pyrimidine
with idine
The name of the nucleoside is given by replacing ine in the purine with
osine for purines
What is a nucleoside?
Purine
Base Sugar Nucleoside
Adenine Ribose Adenosine
Adenine deoxy ribose deoxy adenosine.
Guanine ribose Guanosine .
Guanine deoxyribose deoxy guanosine
Pyrimidines
Base Sugar Nucleoside
Cytosine ribose Cytidine
Cytosine deoxyribose deoxycytidine
Thymine ribose Thymidine
Thymine deoxyribose deoxycytidine
Uracil ribose Uridine
Uracil deoxyribose deoxyuridine
What is a nucleoside?
Nucleoside are used as substrate in the synthesis of nucleic
acids.
However he nucleosides must be activated for them to participating in
the synthesis of nucleic acids.
Activation of nucleosides involves the phosphorylation reaction using a
high energy compound such as ATP.
This phosphorylation reaction is is an enzymatic reaction.
The product of phosphorylation is a nucleotide, which is the activated
substrate for synthesis of nucleic acid.
What are nucleoside analogues?
Nucleoside analogues are compound that have similar
chemical structure as nucleosides.
However he nucleosides must be activated for them to participating in
the synthesis of nucleic acids.
Activation of nucleosides involves the phosphorylation reaction using a
high energy compound such as ATP.
This phosphorylation reaction is is an enzymatic reaction.
The product of phosphorylation is a nucleotide, which is the activated
substrate for synthesis of nucleic acid.
What are nucleoside analogues?
Deoxythymidine may be modified by replacing the
hydroxide at C3’ with azido group to form 3’-Azido- 2’,3’ –dideoxy
thymidine a deoxythymidine analogue
The common name of 3’-Azido- 2’,3’ -dideoxy thymidine is Zidovudine oe
AZT or Retrovir.
What are nucleoside analogues?
Deoxythymidine may be modified by removing the
hydroxide at C3’ and a hydrogen at C2’, creating a double bond between
2’ and 3’ to form a deoxythymidine analogue called 2’,3’ –didehydroxy-
2’,3’ –dideoxythymidine.
The common name of 2’,3’ –didehydroxy- 2’,3’ –dideoxythymidine is
stavudine or d4T.
What are nucleoside analogues?
Deoxycytidine may be modified by replacing the
hydroxide at C3’ together with C3’ with Sulphur atom to form 2’,3’
–dideoxy- 3’-Thia- cytidine.
The common name of 2’,3’–dideoxy- 3’-Thia- cytidine is lamuvudine.
What are nucleotide?
Nucleotide is a phosphate salt of a nucleoside.
It is formed when a nucleosides is phosphorylated using a high energy
compound such as ATP.
Nucleotides may be classified as ribonucleotide and deoxyribonucleotide
depending on the pentose sugar present.
The nucleotides are the monomers of nucleic acids.
What are nucleotide?
Base Nucleoside Nucleotide Nucleic acid
Purines
Adenine Adenosine Adenylate RNA
Deoxyadenosine Deoxyadenylate DNA
Guanine Guanosine Guanylate RNA
Deoxyguanosine Deoxyguanylate DNA
Pyrimidines
Cytosine Cytidine Cytidylate RNA
Deoxycytidine Deoxycytidylate DNA
Thymine Thymidine or Thymidylate or DNA
deoxythymidine deoxythymidylate
Uracil Uridine Uridylate RNA
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