Nucleic Acids

Pedro Javier del Rivero

Morfín
Definition and Application
• A nucleic acid is a
macromolecule
composed of chains
of monomeric
nucleotides.
• These molecules
carry genetic
information, form
structures and
store energy in
high energy
(phosphonahydric)
bonds.
Definition and Application
• The most common
nucleic acids
found in nature
are ribonucleic
and
deoxyribonucleic
acid (RNA and DNA,
respectively).
• They are universal
in all living
things and were
first discovered
Friedrich
Miescherin 1871.
Structure
• Nucleotides are the building blocks of
nucleic acids; they are composed of
three main parts:
▫ A nitrogen containing base
▫ A 5-carbon sugar (ribose or deoxyribose)
▫ A phosphate group

Structure
• The combination of bases and sugars is
called nucleoside; these also exist in
activated forms containing two or three
phosphates.
• This phosphorylated form of nucleosides
forms the nucleotide itself.
•
Structure
• The three kinds
of chemical
bonds acting
over this kind
of molecules are
▫ β-N-glycosisdic
bonds between
C-1 of the
pentose and N-1
of the
pyrimidines or
the N-9 of the
purines
Structure
▫ Phosphodiester
linkages
between the
phosphoryl
groups and the
C-2, C-3 and C-5
of the pentose;
these form the
backbone of the
nucleic acids.
▫ Hydrogen bonds
between purine
and pyrimidine
Differences between Ribose and
Deoxyribose
• The main structural difference between
ribose and deoxyribose is the lack of a
hydroxyl group in the second carbon of
deoxyribose (that is the reason for the
name), having instead just another
hydrogen.
Differences between Ribose and
Deoxyribose
• This leaves
deoxyribose with
only two active
sites for
phosphorylation (3’
and 5’), while
ribose has 3 (2’, 3’
and 5’).
• Ribose is the
pentose sugar
found in RNA, while
deoxyribose is the
sugar found in DNA. Lack
• of O
Purines and Pyrimidines
• Bases found in
nucleotides are
derivativesof
either purine or
pyrimidine.
• Pyrimidine has a
single ring
containing four
carbons and two
nitrogen atoms,
while purine has a
fused pyrimidine-
imidazole ring
system.
Purines and Pyrimidines
• There are 5common
bases found in
nature: thymine,
cytosine, uracil
(pyrimidines),
adenine and
guanine (purines);
uracil is just
found in
ribonucleotides,
and thymine is
just found in
deoxyribonucleotid
Adenosine Triphosphate
• ATP is a
multifunctional
nucleotide used in
cells as a
coenzyme. It is
often called the
“molecular unit of
currency” of
energy transfer.
• It is formed by the
nucleotide
adenosine bonded
to 3 phosphates,
each one joined by
Adenosine Triphosphate
• This bonds are
formed by the
dehydration of
phosphoric acid
derivatives.
• Therefore, the
release of energy
stored in these
bonds is achieved
after hyrolysis.
• ATP is the final
product of the
cellular
respiration.
Synthesis of Nucleic Acids
• DNA Replication.
Synthesis of a new
strand of DNA is
achieved by the
successive
addition of
nucleotides to the
end of a growing
chain; this
polymerization is
catalyzed by DNA
polymerase.
Synthesis of Nucleic Acids
• This enzyme
catalyzes the
formation of a
phosphodiester
linkage between
the incoming
deoxyribonucleosid
e triphosphate
(dNTP) and the
growing chain;
then it forms a
base pair with a
residue of the
Synthesis of Nucleic Acids
• Once a correct base
pair has formed,
the free 3’
hydroxyl of the
DNA chain carries
out a nucleophilic
attack on the α-
phosphorus of the
incoming dNTP; the
resting phosphates
are hydrolyzed,
which makes the
polymerization
irreversible.
Forces Stabilizing DNA Helix
• Stacking
Interactions.
Stacked base pairs
form van der Waals
contacts. These
forces are based
on the dipolarity
of nuclei in atoms,
which generate
attraction and
repulsion forces.

Forces Stabilizing DNA Helix
• Hydrogen Bonds.
Stabilizing force.
They are strong
enough to confer
structural stability,
but weak enough to
be broken readily.
This happens when a
hydrogen atom bonded
to a highly
electronegative atom
gets close enough to
another highly EN
atom.
Forces Stabilizing DNA Helix
• Hydrophobic Effects. Burying hydrophobic
bases in the interior of the double helix
gives more stability to the chain.

Forces Stabilizing DNA Helix
• Charge-Charge Interactions. Electrostatic
repulsion of the negatively charged
phosphate groups in the backbone chain is
a potential instability source, so this
repulsion is minimized by the presence of
cationssuch as Mg 2+

References

• Horton HR, Moran LA, Scrimgeour KG,

Perry MD, Rawn JD. (2006). Principles
of Biochemistry. (4th ed.) Upper
Saddle River, NJ: Pearson Education
Inc.