Section:

BIOMOLECULES
Subsection:
Nucleic acids

PhD. Luis Eduardo García

Amézquita
garcia.amezquita@tec.mx
Major nitrogenous bases
Can be found in large
quantities in the nucleic
acids of all species
Purines Pyrimidines

Adenine Cytosine
DNA, RNA DNA, RNA

Uracil
Guanine Thymine RNA
DNA, RNA DNA
NUCLEIC ACIDS 1
Minor nitrogenous bases
Can be found in small quantities
in the nucleic acids of many
species, and are derived from
the major bases
1-methyl adenine N6-methyl adenine
tRNA DNA, bacteria, and
inferior organisms

5-hydroximehylcytosine 5-methyl cytosine N4-methyl cytosine

DNA, Phage T4 DNA, bacteria, plantae DNA, bacteria
and vertebrates NUCLEIC ACIDS 2
 Nucleosides N-glycosidic
bond
N9 Purines Nitrogenous Sugar
N1 Pyrimidines bases
+ (Pentose)
C1

β-D-Ribofuranose β-D-Deoxyribofuranose

Ribonucleoside Deoxyribonucleoside
Adenosine (A) Deoxyadenosine (dA)
Guanosine (G) Deoxyguanosine (dG)
Cytidine (C) Deoxycytidine (dC)
Uridine (U) Thymidine (dT)

NUCLEIC ACIDS 3
 Nucleosides
Purines

Adenine 9´

condensation
H
H2O
+ N-glycosidic
H2O bond
OH hydrolysis

Adenosine (A)
β-D-Ribofuranose

NUCLEIC ACIDS 4
 Nucleosides
Pyrimidines

Cytosine 1´

H condensation
H2O
+ N-glycosidic
H2O bond
OH hydrolysis

Cytidine (C)
β-D-Ribofuranose

NUCLEIC ACIDS 5
 Nucleosides
Conformers

Anti Syn Anti Syn

Deoxyadenosine (dA) Deoxycytidine (dC)

NUCLEIC ACIDS 6
 Nucleosides
Products and medical uses

N9- β-D-Arabinofuranosyladenine 2’3’ dideoxyinosine

N9- β-D-Arabinofuranosylcytosine 3’azido-2,3 dideoxythymine

Microbial source. Antiviral and Synthetic sources. Antiviral function.

anticarcinogenic activity. Ophthalmic use A competitive inhibitor of the reverse
(Type I Herpes) transcriptase enzyme of HIV
NUCLEIC ACIDS 7
 Nucleotides
Basic structural unit

C5
Nitrogenous Sugar Phosphoric
+ +
bases (Pentose) acid (1 – 3)

Phosphoric
Nucleosides ester

NUCLEIC ACIDS 8
 Nucleotides
Basic structural unit
H
(ATP)

+ +

condensation
H2O
HO
H2O
hydrolysis
Adenosine
5’-monophosphate
(AMP)
Adenosine (A) NUCLEIC ACIDS 9
NUCLEIC ACIDS 10
 Nucleotides
Basic structural unit

Ribonucleotides
NUCLEIC ACIDS 11
 Nucleotides
Basic structural unit

Deoxyribonucleotides
NUCLEIC ACIDS 12
Primary Structure
Polynucleotides 3’
Is the linear order of
nucleotides in polymeric
nucleic acids 5’

4’ 1’
3’ 2’ 5’
Pyrophosphate
(PPi)

Phosphodiester
+ 5’

5’ 4’ 1’ 5’

3’ 2’
4’ 1’ 4’ 1’

3’ 2’ 3’ 2’

Deoxynucleoside
Polynucleotide with triphosphate Polynucleotide with
N residues N+1 residues NUCLEIC ACIDS 13
Primary Structure
Polynucleotides
“directionality”
Characteristics 1st

5’ phosphate 3’ hydroxyl

2nd “sequence” Gene is a particular

DNA sequence

NUCLEIC ACIDS 14
Primary Structure
Polynucleotides
Genetic information is
stored in the primary
structure

Oswald Avery
Fred Griffith

https://www.dnalc.org/view/16375-Animation-17-A-gene-is-made-of-DNA-.html

NUCLEIC ACIDS 15
Secondary structure
Polynucleotides
Is the three-dimensional
arrangements of the nucleotide
residues with respect to one another

Watson and
Crick
Rosalind
Franklin
Double-helix model
NUCLEIC ACIDS 16
Secondary structure
Polynucleotides

Adenine Thymine
DNA, RNA = DNA

Guanine Cytosine
DNA, RNA = DNA, RNA

Erwin
Chargaff =
Purines Pyrimidines
NUCLEIC ACIDS 17
Secondary structure
Polynucleotides
Watson and Crick Helical structures with a repeat distance of
double-helix model 10 nucleotides (10.5)
The distance at which the helix makes one
turn is 3.4 nm
The distance between two successive
nucleotides is 0.34 nm

NUCLEIC ACIDS 18
Secondary structure
Polynucleotides
Watson and Crick
double-helix model

Hydrogen bonds

NUCLEIC ACIDS 19
Secondary structure
Polynucleotides
Watson and Crick
double-helix model
1. Two spiral grooves (major and
minor)
2. Two stranded DNA structures run
in opposite directions Minor
5’ groove
3’

Major
groove

3’ 5’ NUCLEIC ACIDS 20
 Three models of DNA
Secondary structure
Polynucleotides Replication

Watson and Crick Parental

double-helix model DNA

Parent
strand
Conservative

Semi
Daughter strands conservative

Dispersive

NUCLEIC ACIDS 21
Secondary structure
Polynucleotides
Alternatives structures: A helix

B helix
Watson and
Crick’s
Minor Major
groove groove

DNA

Low humidity DNA, RNA,

and DNA-RNA hybrids
NUCLEIC ACIDS 22
Secondary structure
Polynucleotides
Alternatives structures:

There is not convincing evidence of the existence of Z

structure in alive cells. However, the transition to this form may
regulate the gene expression. NUCLEIC ACIDS 23
Secondary structure
Polynucleotides 2012

Phage λ Phage ϕX174

E. coli

NUCLEIC ACIDS 24
Tertiary structure
Polynucleotides
Is the higher-order folding of the
secondary structure
SUPERCOILING

DNA-ligases

Topoisomerases

Topoisomers NUCLEIC ACIDS 25

Tertiary structure
Polynucleotides
Hairpins and Cruciforms

palindromic

tRNA

Hoogsteen-type
Triple-stranded DNA NUCLEIC ACIDS 26
 RNA polymerase
Functions
Polynucleotides

Transcription

Translation

NUCLEIC ACIDS 27