Purines and Nucleic acids

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 Purine

 Any of a class of organic compounds of the heterocyclic series

characterized by a two-ringed structure composed of carbon and
nitrogen atoms.
 The simplest of the purine family is purine itself, a compound
with a molecular formula C5H4N4.
 Purine is not common, but the purine structure occurs in many
natural substances.
 Nitrogenous bases,
 common purine bases – adenine and guanine – in the tautomeric
forms predominant at pH 7.

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PURINE RIBONUCLEOTIDES: formed de novo
– i.e., purines are not initially synthesized as free bases
– First purine derivative formed is Inosine Mono-phosphate (IMP)
• The purine base is hypoxanthine
• AMP and GMP are formed from IMP

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Other naturally occurring purine derivatives – hypoxanthine, xanthine,
and uric acid.
IMP is deribosylated
to hypoxanthine

Uric acid
 the first purine derivative to be
discovered, was isolated in 1776 from
urinary calculi; xanthine was obtained
from the same source in 1817.
 Uric acid is the end product of purine
metabolism in humans

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 Purine biodegradation in mammals (humans) leads to uric
acid
Xanthine oxidase oxidizes hypoxanthine to xanthine and
xanthine to uric acid Guanine can be
deaminated to
give xanthine

Uric acid is
excreted as urate
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 Nucleic acids
• Nucleic acids (DNA and RNA) are polymers whose building
blocks are nucleotides,
Nucleosides and nucleotides
• Nucleotides are the combinations of three parts:
• a heterocyclic base,
• a sugar, and
• phosphate.
• The most significant difference in the nucleotides comprising
DNA and RNA is the sugar unit, which is deoxyribose in DNA
and ribose in RNA.
• Nucleoside is a nucleotide lacking of phosphate group (base–sugar
combination).

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• Nucleic acids (DNA & RNA) 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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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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C)Synthetic analogs of naturally occurring
nucleotides. e.g.
a- 5flurouracil These compounds inhibit the
growth of cancer cells by:
• inhibiting their enzyme activity or
• inhibiting the synthesis of either DNA or RNA
b- Allopurinol, a purine analog is
widely used in the treatment of gout

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Xanthine
• Is a purine base found in most human body
tissues, fluids and in other organisms.
Eg. caffeine and Theo bromine (stimulants).
• Xanthine is a product on the pathway of purine
degradation.
• It is created from guanine by guanine
deaminase.
• It is created from hypoxanthine by xanthine
oxidoreductase.

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Selected xanthines

IUPAC nomenclature
Name R1 R2 R3 Found In

3,7-dihydro-purine-
Xanthine H H H Plants, animals
2,6-dione

Theophylli Tea, Cacao (chocolate),

1,3-dimethyl-7H-
ne CH3 CH3 H Yerba mate, Kola
purine-2,6-dione

Cacao (chocolate), Yerba

Theobromi
CH3 CH3 ??-3,7-dimethyl-1H- mate, Kola, Guayusa, Ho
ne H
purine-2,6-dione lly
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Basic ring structure of
xanthine Theobromine

Caffeine
Theophylline
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 Caffeine
• Caffeine belongs to a group of chemicals called
methylxanthines.
• Occur naturally in a number of plant derived
foodstuffs, in particular coffee, tea, cola drinks
and cocoa products.
• Caffeine is both water and fat-soluble

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Properties
• Caffeine is
• a bitter, white crystalline purine,
• a methylxanthine alkaloid, and
• Chemically related to
the adenine and guanine bases

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Chemistry of caffeine
– Pure anhydrous caffeine is a bitter-tasting white
odorless powder with a melting point of 235–238 °C.
– Moderately soluble in water at room temperature, but
very soluble in boiling water.
– It is also moderately soluble in ethanol.
– It is weakly basic
– It does not contain any stereogenic centers
– The xanthine core of caffeine contains two fused
rings, a pyrimidinedione and imidazole.

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 Theobromine
• Formerly known as xantheose, is a
bitter alkaloid of the cacao plant,
• It is found in chocolate, as well as in a number of
other foods, including the leaves of the tea plant,
and the kola (or cola) nut.
• It is classified as a xanthine alkaloid.

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Uses
• Theobromine is
– a vasodilator (a blood vessel widener),
– a diuretic (urination aid), and
– heart stimulant.

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 Theophylline
• Known as 1,3‑dimethylxanthine, is a methylxant
hine drug.
Uses
• Theophylline is used in therapy for respiratory
diseases such as chronic obstructive pulmonary
disease (COPD) and asthma.

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 Medical uses of theophylline
The main actions of theophylline involve:
– relaxing bronchial smooth muscle
– increasing heart muscle contractility and efficiency
– increasing heart rate
– increasing renal blood flow
– anti-inflammatory effects
– central nervous system stimulatory effect mainly on
the medullary respiratory center.

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 THANKS

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