BCH 2301
Nucleic Acid Chemistry
Murtala Ya’u (PhD)
Nucleic acids
Nucleic acids, deoxyribonucleic acid (DNA) and
ribonucleic acid (RNA), carry genetic information which is
read in cells to make the RNA and proteins by which living
things function. The well-known structure of the DNA double
helix allows this information to be copied and passed on to
the next generation. Thus, nucleic acid conserves and
transmits genetic information with remarkable fidelity. It
simply holds the code of life!
Component
of DNA &
RNA
Chemic
2nd
al
messenge energy
rs Functio (ATP &
(cAMP & GTP)
cGMP) n in the
Cell
Activated Compone
precursor nt of
s NAD, FAD
e.g. UDP- & CoASH
glucose
Deoxyribonucleic acid, DNA
Nucleic acid
Ribonucleic acid, RNA
1. The components of DNA and RNA
• DNA and RNA are polymers of
nucleotide units.
•DNA (RNA) consists of 4 kinds of
ribonucleotide units linked together
through covalent bonds.
• Each nucleotide unit is
composed of a nitrogenous
base
a pentose sugar
a phosphate group
Nitrogenous Bases
Nitrogenous Base: They comprise
pyrimidine or purine base. DNA contains
adenine (A), guanine (G), cytosine (C) and
thymine (T) whereas RNA contains adenine,
guanine, cytosine and uracil (U)
The bases are planar, aromatic, and
heterocyclic.derivetives of purine or
pyrimidine
Numbering of bases is “unprimed”
Nitrogenous Bases contd……
Nucleic Acid Bases
Sugars
• Pentoses (5-C sugars)
• Numbering of sugars is
“primed”
Sugars
D- 2’
Ribose Deoxyribose
*Lacks a 2’-OH group
Nucleosides
• Result from linking one of
the sugars with a purine or
pyrimidine base through an
N-glycosidic linkage
– Purines bond to the C1’ carbon
of the sugar at their N9 atoms
– Pyrimidines bond to the C1’
carbon of the sugar at their
N1 atoms
Nucleosides
Phosphate Groups
• Mono-, di- or triphosphates
• Phosphates can be bonded to
either C3 or C5 atoms of the
sugar
Nucleotides
• Result from linking one or more
phosphates with a nucleoside onto
the 5’ end of the molecule through
esterification
Deoxyadenosine monophosphate
phosphate
nucleic acid nucleotides pentose
nucleosides
bases
NH2
N
O
HO O CH2 N O
O
P
OH OH OH
Nucleotides
• RNA (ribonucleic acid) is a
polymer of ribonucleotides
• DNA (deoxyribonucleic
acid) is a polymer of
deoxyribonucleotides
• Both deoxy- and
ribonucleotides contain
Adenine, Guanine and
Cytosine
Nucleotide Functions
1. Nucleotides are the building block of DNA and
RNA. They contain genetic information
2. Nucleotides act as coenzymes, which are required
to catalyse many biochemical reactions by enzymes
3. Energy is stored in our body as ATP. When there is
a need for the energy they get converted to ADP or
AMP. ATP also acts as a coenzyme
4. NAD, NADP has an essential role to play in many
redox reactions, they act as an electron carrier
5. cAMP helps in transporting chemical signals and
metabolic regulation
Naming Conventions
• Nucleosides:
– Purine nucleosides end in “-
sine”
• Adenosine, Guanosine
– Pyrimidine nucleosides end in
“-dine”
• Thymidine, Cytidine, Uridine
• Nucleotides:
– Start with the nucleoside name
from above and add
“mono-”, “di-”, or
Structure of RNA
RNA is a single stranded molecule containing a
ribose-phosphate backbone upon which
nucleobases; purines and pyrimidines are
attached to the C-1’ of the ribose moiety. The
single strand runs from 5’ to 3’ direction. There
are three types of RNAs; the messenger RNA
(mRNA), transfer RNA (tRNA) and ribosomal
RNA (rRNA)
5’end
Phosphodiest
er
bond
3’ end: free hydroxyl
(-OH) group
•3’,5’ phosphodiester bond link
nucleotides together to form
•Watson, Crick, and
Wilkins shared the Nobel
Prize in medicine or
physiology in 1962 for this
brilliant accomplishment.
•The discovery of the
DNA double helix
revolutionized biology: it
led the way to an
understanding of gene
function in molecular terms
(their work is recognized to
mark the beginning of
Structure of DNA
The Watson and Crick DNA model reveals
some salient features of the double stranded
DNA. The double helix have complementary
base sequences and anti-parallel orientations.
Alternating deoxyribose sugar and phosphates
form the backbone of the structure and the
nitrogenous bases are stacked inside, forming a
twisted rod-like structure of 2nm in diameter.
Purines always pair with pyrimidines: A-T and
G-C base pairing format.
Nucleic acids Denaturation
DNA denaturation refers to the loss of
hydrogen bonding between the complementary
paired bases due to an increase in temperature,
and the subsequent unwinding and separation
of double-stranded helical DNA into single-
stranded coiled DNA. The temperature at
which the double-stranded DNA separates into
single-stranded DNA is called DNA melting
temperature.
