Chapter 22
Lecture
Outline
Prepared by
Andrea D. Leonard
University of Louisiana at Lafayette
Copyright © The McGraw-Hill Companies, Inc. Permission required for reproduction or display.
Nucleosides and Nucleotides
Introduction
•Nucleic acids are unbranched polymers composed
of repeating monomers called nucleotides.
•There are two types of nucleic acids: DNA and
RNA.
•DNA (deoxyribonucleic acid) stores the genetic
information of an organism and transmits that
information from one generation to another.
•RNA (ribonucleic acid) translates the genetic
information contained in DNA into proteins needed
for all cellular function.
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Nucleosides and Nucleotides
Introduction
•The nucleotide monomers that compose DNA and
RNA consist of: a monosaccharide, a N-containing
base, and a phosphate group:
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Nucleosides and Nucleotides
Introduction
•DNA molecules contain several million nucleotides,
while RNA molecules have only a few thousand.
•DNA is contained in the chromosomes of the
nucleus, each chromosome having a different type
of DNA.
•Humans have 46 chromosomes (23 pairs), each
made up of many genes.
•A gene is the portion of the DNA molecule
responsible for the synthesis of a single protein.
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Nucleosides
Joining a Monosaccharide and a Base
•In RNA the monosaccharide is the aldopentose
D-ribose.
•In DNA, the monosaccharide is the aldopentose
D-2-deoxyribose.
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Nucleosides
Joining a Monosaccharide and a Base
•The N-containing base is one of 5 types.
•Cytosine (C), uracil (U), and thymine (T) are all
based on the structure of pyrimidine.
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Nucleosides
Joining a Monosaccharide and a Base
•Adenine (A) and guanine (G) are based on the
structure of purine.
•DNA contains bases A, G, C, and T.
•RNA contains bases A, G, C, and U.
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Nucleosides
Joining a Monosaccharide and a Base
•A nucleoside is formed by joining the anomeric
carbon of the monosaccharide with a N atom
of the base.
•To name a nucleoside derived from a pyrimidine
base, use the suffix “-idine”.
•To name a nucleoside derived from a purine base,
use the suffix “-osine”.
•For deoxyribonucleosides, add the prefix “deoxy-”.
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Nucleosides
Joining a Monosaccharide and a Base
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Nucleosides
Joining a Monosaccharide and a Base
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Nucleotides
Joining a Nucleoside with a Phosphate
•Nucleotides are formed by adding a phosphate
group to the 5′-OH of a nucleoside.
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Nucleotides
Joining a Nucleoside with a Phosphate
•The resulting nucleotide:
•The name cytidine 5′-monophosphate is abbreviated
as CMP. 12
Nucleotides
Joining a Nucleoside with a Phosphate
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Nucleotides
Joining a Nucleoside with a Phosphate
•The resulting nucleotide:
•The name deoxyadenosine 5’-monophosphate is
abbreviated as dAMP.
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Nucleotides
Joining a Nucleoside with a Phosphate
•ADP is an example of a diphosphate:
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Nucleotides
Joining a Nucleoside with a Phosphate
•ATP is an example of a triphosphate:
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Nucleic Acids
•Nucleic acids (DNA and RNA) are polymers of
nucleotides joined by phosphodiester linkages.
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Nucleic Acids
•A polynucleotide contains a backbone consisting
of alternating sugar and phosphate groups.
•The identity and order of the bases distinguish
one polynucleotide from another (primary
structure).
•A polynucleotide has one free phosphate group
at the 5’ end and one free OH group at the 3’ end.
•In DNA, the sequence of the bases carries the
genetic information of the organism.
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Nucleic Acids
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Nucleic Acids
•The previous chain can
be abbreviated:
•This polynucleotide
would be named CATG,
reading from the 5’ end
to the 3’ end.
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The DNA Double Helix
•The DNA model was initially proposed by Watson
and Crick in 1953.
•DNA consists of two polynucleotide strands that
wind into a right-handed double helix.
•The two strands run in opposite directions; one
runs from the 5’ end to the 3’ end and the other
runs from the 3’ end to the 5’ end.
•The sugar-phosphate groups lie on the outside
of the helix and the bases lie on the inside.
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The DNA Double Helix
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The DNA Double Helix
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The DNA Double Helix
•The bases always line up so that a pyrimidine
derivative can hydrogen bond to a purine
derivative on the other strand.
•Thus, there are complementary base pairs that
always hydrogen bond together in a particular
manner.
•Adenine pairs with thymine with 2 hydrogen
bonds to form an A—T base pair.
•Cytosine pairs with guanine using 3 hydrogen
bonds to form a C—G base pair.
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