David L. Nelson and Michael M.

Cox

LEHNINGER
PRINCIPLES OF BIOCHEMISTRY
Sixth Edition

CHAPTER 8
Nucleotides and Nucleic Acids

© 2013 W. H. Freeman and Company

 Cellular Processes

replication
DNA
transcription

RNA (mRNA)

translation

Proteins

Lipids Carbohydrates
Structure of Nucleotides
 Phosphodiester
linkages in the
covalent backbone
of DNA and RNA
Hydrolysis of RNA under alkaline conditions
 Absorption
spectra of the
common
nucleotides
 Hydrogen bonding between
complementary DNA strands
Watson – Crick model for the structure of DNA
Certain DNA sequences adopt unusual structures
A single DNA strand with self complementary
sequences can form a hairpin structure
Double stranded DNA
with self
complementary
sequences can form a
cruciform structure
 Hoogsteen base pairs form in triplex DNA
A single strand of DNA, typically a string of pyrimidines, hydrogen bonds in the
major groove of a double-stranded DNA

Red strand is in the

major groove
Four DNA strands containing a high proportion of
guanosines can form a G tetraplex
 Cellular Processes

replication
DNA
transcription

RNA (mRNA)

translation

Proteins

Lipids Carbohydrates
 mRNA molecules can be monocistronic (containing
one gene) or polycistronic (containing multiple genes)
In eukaryotes most mRNAs are monocistronic
In prokaryotes many mRNAs are polycistronic
Secondary structure of RNA
 M1 RNA
component of the
enzyme Rnase P of
E. coli
 Reversible
denaturation and
annealing (renaturation)
of DNA
When DNA is denatured the melting point is when half
of the DNA is present as separated single strands

The greater the G-C content, the higher the melting point (tm)
Electron micrograph showing partially denatured DNA
Red arrows indicate regions of high A-T content, which denature first
Spontaneous loss of
an exocyclic amino
group is deamination

Around 100 times

per day in a cell
Nitrous acid (HNO2) promotes deamination reactions
 Hydrolysis of the
bond between the
base and the ribose
creates an apurininc
site in DNA

Around 10,000 times

per day in a cell
Pyrimidine dimers are induced by exposure to UV light
 Nucleotides
found in
biomolecules