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Lecturer

The document discusses nucleic acids, specifically DNA and RNA. It describes how nucleic acids were first discovered and their importance as carriers of genetic information. The key components of nucleotides, which are the monomers that make up nucleic acids, are discussed including the nitrogenous base, phosphate group, and pentose sugar. The structures of DNA and RNA are compared, noting they have complementary base pairing and that RNA contains ribose while DNA contains deoxyribose. The major types of RNA are also outlined.

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34 views42 pages

Lecturer

The document discusses nucleic acids, specifically DNA and RNA. It describes how nucleic acids were first discovered and their importance as carriers of genetic information. The key components of nucleotides, which are the monomers that make up nucleic acids, are discussed including the nitrogenous base, phosphate group, and pentose sugar. The structures of DNA and RNA are compared, noting they have complementary base pairing and that RNA contains ribose while DNA contains deoxyribose. The major types of RNA are also outlined.

Uploaded by

atef.salman.gr
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Chemistry of biomolecules

Lecturer 8
Lecturer 9

1
Nucleic acids
Introduction
The first isolation of what we now refer to as DNA
was accomplished by Johann Friedrich Miescher circa
‫حوالي‬1870. He reported finding a weakly acidic
substance of unknown function in the nuclei of human
white blood cells, and named this material "nuclein". A
few years later, Miescher separated nuclein into
protein and nucleic acid components.

In the 1920's nucleic acids were found to be major


components of chromosomes, small gene-carrying
bodies in the nuclei of complex cells. Elemental
analysis of nucleic acids showed the presence of
phosphorus, in addition to the usual C, H, N & O.
Unlike proteins, nucleic acids contained no sulfur.
Nucleic Acids
Importance:
-The chemical link between generations
-The source of genetic information in
chroamosomes
-Dictate amino-acid sequence in proteins
-Give information to chromosomes, which is
then passed from parent to offspring‫ذزية‬
Nucleic acids
The nucleic acids, Deoxyribonucleic
Acid (DNA) and Ribonucleic acid
(RNA) are respectively, the molecules
that preserve hereditary information
that translate it in a way that allow
the synthesis of varied proteins in
the cell.

Mild hydrolysis of these nucleic acids


yield their monomeric units,
compounds called nucleotides
Nucleotides and nucleic acids
Nucleotides are the building blocks of nucleic acids

Nucleotide
RNA DNA
Nucleotides also play other important roles in the cell
Xx Roles of nucleotides

• Building blocks of nucleic acids (RNA, DNA)


Analogous to amino acid role in proteins
• Energy currency in cellular metabolism (ATP:
adenosine triphosphate)
• Structural components of many enzyme
cofactors (NAD: nicotinamide adenine
dinucleotide)
Xx Roles of nucleic acids
• DNA contains genes, the information needed to
synthesize functional proteins and RNAs
• DNA contains segments that play a role in regulation of
gene expression (promoters)
• Ribosomal RNAs (rRNAs) are components of ribosomes,
playing a role in protein synthesis
• Messenger RNAs (mRNAs) carry genetic information
from a gene to the ribosome
• Transfer RNAs (tRNAs) translate information in mRNA
into an amino acid sequence
• RNAs have other functions, and can in some cases
perform catalysis
Structure of nucleotides
Nucleotides have three characteristic components:

A nitrogenous base
A phosphate group (pyrimidines or purine)

A pentose sugar
Structure of nucleosides

Remove the phosphate group, and you have a nucleoside.

H
Structure of nucleotides
Below is the general structure of a nucleotide. The
pentose sugar, the base, and the phosphate moieties
all show variations among nucleotides.
The ribose sugar
Ribose

• Ribose (b-D-furanose) is
a pentose sugar (5-
membered ring). 5
• Note numbering of the 1
carbons. In a nucleotide, 4
"prime" is used (to
differentiate from base 3
numbering). 2
Deoxyribose
• An important derivative of
ribose is 2'-deoxyribose,
or just deoxyribose, in
which the 2' OH is
replaced with H.
• Deoxyribose is in DNA
(deoxyribonucleic acid)
• Ribose is in RNA
(ribonucleic acid).
The purine or pyrimidine base
Major bases in nucleic acids
• The bases are
abbreviated by their first
letters (A, G, C, T, U).
• The purines (A, G) occur
in both RNA and DNA

• Among the pyrimidines, C


occurs in both RNA and
DNA, but
• T occurs in DNA, and
• U occurs in RNA
The phosphate
Variation in phosphate group

• Adenosine 3', 5'-cyclic


monophosphate (cyclic AMP,
or cAMP) is an important
regulatory nucleotide.
• In hydrolysis of RNA by
some enzymes,
ribonucleoside 2',3'-cyclic
monophosphates are isolable
intermediates;
ribonucleoside 3'-
monophosphates are end
products
• Another variation - multiple
phosphates (like ATP).
The structure elements of the most common nucleotides
Nucleotides in nucleic acids
• Bases attach to the C-1' of ribose or deoxyribose
• The pyrimidines attach to the pentose via the N-1 position of
the pyrimidine ring
• The purines attach through the N-9 position
• Some minor bases may have different attachments.
Deoxyribonucleotides
2'-deoxyribose sugar guanine
adenine
with a base (here, a purine,
adenine or guanine)
attached to the C-1'
position is a
deoxyribonucleoside
(here deoxyadenosine and
deoxyguanosine).

Phosphorylate the 5' position


and you have a nucleotide(here,
deoxyadenylate or
deoxyguanylate)

Deoxyribonucleotides are abbreviated (for example) A, or


dA (deoxyA), or dAMP (deoxyadenosine monophosphate)
The major deoxyribonucleotides

adenine guanine thymine cytosine


Ribonucleotides
• The ribose sugar with a uracil cytosine
base (here, a pyrimidine,
uracil or cytosine) attached
to the ribose C-1' position
is a ribonucleoside (here,
uridine or cytidine).
• Phosphorylate the 5'
position and you have a
ribonucleotide (here,
uridylate or cytidylate)

• Ribonucleotides are abbreviated (for example) U, or UMP


(uridine monophosphate)
The major ribonucleotides

adenine guanine uracil cytosine


Nucleotide nomenclature
Nucleotide nomenclature
Nucleic acids
Nucleotide monomers
can be linked together via a
phosphodiester linkage
formed between the 3' -OH
of a nucleotide
and the phosphate of the
next nucleotide.
Two ends of the resulting poly-
or oligonucleotide are defined:
The 5' end lacks a nucleotide at
the 5' position,
and the 3' end lacks a nucleotide
at the 3' end position.
Compare polynucleotides and polypeptides

• As in proteins, the sequence of side chains


(bases in nucleic acids) plays an important
role in function.
• Nucleic acid structure depends on the
sequence of bases and on the type of ribose
sugar (ribose, or 2'-deoxyribose).
• Hydrogen bonding interactions are
especially important in nucleic acids.
Nucleoside Base Distribution in DNA
Base Composition (mole %) Base Ratios
Organism Ratio (A+T)/(G+C)
A G T C A/T G/C

Human 30.9 19.9 29.4 19.8 1.05 1.00 1.52

Chicken 28.8 20.5 29.2 21.5 1.02 0.95 1.38

Yeast 31.3 18.7 32.9 17.1 0.95 1.09 1.79

Clostridium
perfringens
36.9 14.0 36.3 12.8 1.01 1.09 2.70

Sarcina
lutea
13.4 37.1 12.4 37.1 1.08 1.00 0.35
• From the last table it was found that the
amount of adenine (A) always equaled the
amount of thymine (T), and the amount of
guanine (G) always equaled the amount of
cytosine (C), regardless of the DNA source.
• But the total purines (A and G) and the total
pyrimidines (T and C) were always equal.
• Moreover: %A = %T, and %G = %C
Interstrand H-bonding between DNA bases
DNA structure
• DNA consists of two helical
chains wound around the
same axis in a right-handed
fashion aligned in an
antiparallel fashion.
• There are 10.5 base pairs, or
36 Å, per turn of the helix.
• Alternating deoxyribose and
phosphate groups on the
backbone form the outside
of the helix.
• The planar purine and
pyrimidine bases of both
strands are stacked ‫تتكدس‬
inside the helix.
Two strands of DNA were aligned anti-parallel to each other,
i.e. with opposite 3' and 5' ends, shown in part (a), cross-linked
ribbons in part (b)

.
DNA strands

• The antiparallel strands of DNA are


not identical, but are complementary.
• This means that they are positioned
to align complementary base pairs: C
with G, and A with T.
• So you can predict the sequence of
one strand given the sequence of its
complement.
• Useful for information storage and
transfer!
• Note sequence conventionally is given
from the 5' to 3' end
Write the complementary base
sequence for the matching strand in
the following DNA section:

-A-G-T-C-C-A-A-T-G-C-
• • • • • • • •
• • • • • • • •
• Solution
The complementary base sequence for the
matching strand in the following DNA section:

-A-G-T-C-C-A-A-T-G-C-
• • • • • • • •
• • • • • • • •
-T-C-A-G-G-T-T-A-C-G-
RNA has a rich and varied structure
Watson-Crick
base pairs
(helical segments;
Usually A-form).
Helix is secondary
structure.
Note A-U pairs in
RNA.

DNA can
form
structures
like this as
well.
RNA displays interesting tertiary structure

Single-stranded RNA
right-handed helix
types of RNA
• Messenger RNA (mRNA) carries
coded instructions for protein
synthesis
• Transfer RNA (tRNA) carries
specific amino acids to ribosomes
during protein assembly
• Ribosomal RNA (rRNA) part of
ribosomes
Comparison between DNA & RNA
DNA RNA
Sugar 2'- deoxyribose ribose
Bases Thymine, uracil instead of
cytosine, thymine
adenine,
guanine
Chain long chain of short chain of
nucleotides nucleotides
Occurrence chiefly in nuclei distributed through
the cell
Mol. weight high low
Stability more stable less stable

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