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Nucleic Acid Chemistry Dr: Hussein abdelaziz
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Objectives
By the end of lecture the student should:
Define nucleic acids.
Illustrate structure of nucleotides.
List functions of nucleotides.
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Nucleic acids (DNARNA) are long chains of repeated nucleotides A nucleotide consists of:
1- Nitrogenous base 2- Pentose sugar 3- One or more phosphate groups
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1- Nucleotides
Phosphate Base Sugar
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Sugars
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Nitrogenous bases
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A- Purines
In both DNA & RNA
Guanine Adenine
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B- Pyrimidines
Thymine (DNA) Cytosine Uracil (RNA)
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Nomenclature of nucleotides & nucleosides
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1
2
3
4
5
6
7
8
9
1
23
4
5
Base
(adenine)
Nucleotide
HO P O P O P O CH2
O O O
HOHO HO
Phosphates
C
C
O
C
C
HH H H
XOH
Nucleoside
C H
N
NC
C
C
N
HC
N
NH2
sugar
x = OH in ribose
x = H in deoxyribose
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Pyrimidines Purines
Uracil (U)
Thymine (T)
Cytosine (C)
Guanine (G) Adenine (A)
Uridine
deoxythymidine
Cytidine
deoxycytidine
Guanosine
deoxyguanosine
Adenosine
deoxyadenosine
Nucleoside (RNA)
Deoxynucleoside (DNA)
(base + sugar)
Uridylate
deoxythymidylate
Cytidylate
deoxycytidylate
Guanylate
deoxyguanylate
Adenylate
deoxyadenylate
Nucleotide (RNA) Deoxynucleotide
(DNA) (base + sugar +P)
UMP (Uridylic acid)
CMP
(Cytidylic acid )
GMP
(Guanylic acid )
AMP (Adenylic acid)
Nucleoside Monophosphate
UDP CDP GDP
ADP Nucleoside diphosphate
UTP CTP GTP ATP Nucleoside triphosphate
dTMP(Thymidylic acid) dTDP dTTP
dCMP
dCDP
dCTP
dGMP
dGDP
dGTP
dAMP dADP dATP
Deoxynucleoside mono-di-and tri-
phosphates
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Importance & Functions of nucleotides
A- Building blocks of DNA & RNA
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B- Nucleotide derivatives: 1- ATP formation which is a major source of energy in the cell 2- GTP, UTP, CTP are sources of energy in certain metabolic pathways 3- Formation of coenzymes NAD, NADP, FAD and coenzyme A
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4- cAMP acts as a second messenger inside the cell for many hormones and cGMP act as a cellular mediator
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5- Some nucleotides are important regulators for many metabolic reactions 6- Nucleotides act as carriers of activated intermediates such as: a- UDP- glucose in synthesis of glycogen
b- CDP choline in synthesis of phospholipids
c- GDP mannose in synthesis of glycoproteins
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A- These compounds inhibit the growth of cancer cells by:
• inhibiting their enzyme activity or • inhibiting the synthesis of either DNA or RNA
e.g. 5 flurouracil B- Allopurinol, a purine analog is widely used in the treatment of gout
C- Synthetic analogs of naturally occuring nucleotides