Purine & Pyrimid
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PyrimidinesPyrimidines& PurinesPurines
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Pyrimidines and Purines
In order to understand the structureand properties of DNA and RNA, weneed to look at their structuralcomponents.
We begin with certain heterocyclicaromatic compounds called pyrimidinesand purines.
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• Double helix,• Double strands,
DNADNA
…this structure was proposed in1953 by two Nobel prize winners:
The main role of DNA is the long-termstorage of genetic information (DNA asgenetic material)
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RNA
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Pyrimidines and PurinesPyrimidine and purine are the names ofthe parent compounds of two types ofnitrogen-containing heterocyclicaromatic compounds.
NN
NN
NN
NN
NN
NNHH
PyrimidinePyrimidine PurinePurine
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Pyrimidines that occur in DNA arecytosine and thymine. Cytosine anduracil are the pyrimidines in RNA.
Important Pyrimidines
HHNN
NNHH
OO
OO
UracilUracil
HHNN
NNHH
OO
OO
CHCH33
ThymineThymine
HHNN
NNHH
NNHH22
OO
CytosineCytosine
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Important PurinesAdenine and guanine are the principal
purines of both DNA and RNA.
AdenineAdenine
NN
NN
NNHH22
NN
NNHH
GuanineGuanine
OO
HHNN
NNHH
NN
NN
HH22NN
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Caffeine and Theobromine
Caffeine (coffee) and theobromine (coffeeand tea) are naturally occurring purines.
CaffeineCaffeine
NN
NN
OO
NN
NN
HH33CC
OO
CHCH33
CHCH33
TheobromineTheobromine
OO
HHNN
NNNN
NN
CHCH33
CHCH33
OO
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NucleosidesThe classical structural definition is that a
nucleoside is a pyrimidine or purine N-glycoside of D-ribofuranose or 2-deoxy-D-ribofuranose.
Informal use has extended this definition toapply to purine or pyrimidine N-glycosides ofalmost any carbohydrate.
The purine or pyrimidine part of a nucleosideis referred to as a purine or pyrimidine base.
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Uridine and AdenosineUridine and adenosine are pyrimidine and purine
nucleosides respectively of D-ribofuranose.
UridineUridine(a (a pyrimidinepyrimidine nucleoside) nucleoside)
AdenosineAdenosine(a (a purinepurine nucleoside) nucleoside)
OO
NNHOCHHOCH22
HHNN
OO
OHOHHOHO
OO
NN NN
NN NNHOCHHOCH22 OO
OHOHHOHO
NNHH22
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Nucleotides
They are phosphoric acid esters ofnucleosides.
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Adenosine 5'-Monophosphate (AMP)
Adenosine 5'-monophosphate (AMP) isalso called 5'-adenylic acid.
NN NN
NN NN
OO
OHOHHOHO
NNHH22
OCHOCH22PPHOHO
OO
HOHO
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Adenosine 5'-monophosphate (AMP) isalso called 5'-adenylic acid.
NN NN
NN NN
OO
OHOHHOHO
NNHH22
OCHOCH22PPHOHO
OO
HOHO1'1'
2'2'3'3'
4'4'5'5'
Adenosine 5'-Monophosphate (AMP)
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Adenosine Diphosphate (ADP)
NN NN
NN NN
OO
OHOHHOHO
NNHH22
OCHOCH22PPOO
OO
HOHO
PP
OO
HOHO
HOHO
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Adenosine Triphosphate (ATP)
NN NN
NN NN
OO
OHOHHOHO
NNHH22
OCHOCH22PPOO
OO
HOHO
PP
OO
HOHO
OOPP
OO
HOHO
HOHO
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ATP Stores Energy
AMPAMP
ADPADP
ATPATP Each step is endothermic. Energy for each step comes
from carbohydrate metabolism(glycolysis).
Reverse process is exothermicand is the source of biologicalenergy.
ΔG° for hydrolysis of ATP toADP is –35 kJ/mol
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Adenosine 3'-5'-CyclicMonophosphate (cAMP)
Cyclic AMP is an important regulatorof many biological processes.
NN NN
NN NN
OO
OHOHOO
NNHH22
CHCH22
PPOO
HOHO
OO
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To be continuedTo be continued……