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Chemistry 501 Handout 8 Nucleotides and Nucleic Acids Chapter 8

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Dep. of Chemistry & Biochemistry Prof. Indig Chemistry 501 Handout 8 Nucleotides and Nucleic Acids Chapter 8 Lehninger. Principles of Biochemistry. – PowerPoint PPT presentation

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Title: Chemistry 501 Handout 8 Nucleotides and Nucleic Acids Chapter 8


1
Chemistry 501 Handout 8 Nucleotides and
Nucleic Acids Chapter 8
Lehninger. Principles of Biochemistry. by Nelson
and Cox, 5th Edition W.H. Freeman and Company
2
Structure of nucleotides
3
Major purine and pyrimidine bases of nucleic
acids
4
Conformation of ribose
same side of the plane relative to the C-5 atom
opposite side of the plane relative to the C-5
atom
5
Ribonucleotides of nucleic acids
6
Deoxyribonucleotides of nucleic acids
7
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8
Some minor purine and pyrimidine bases, shown as
the nucleosides
Minor bases of DNA
Minor bases of tRNAs
9
Some adenosine monophosphates
10
Hydrolysis of RNA under alkaline conditions
11
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12
Phosphodiester bonds link successive nucleotides
in nucleic acids
Phosphodiester linkages in the covalent backbone
of DNA and RNA
Some adenosine monophosphates
13
Schematic representation of the nucleotide
sequences of nucleic acids
14
The properties of nucleotide bases affect the
three-dimensional structure of nucleic acids
Free pyrimidine and purine bases may exist in two
or more tautomeric forms depending on the pH.
As a result of resonance, all nucleotide bases
absorb UV light.
15
Hydrogen-bonding patters in the base pairs
defined by Watson and Crick
16
Watson-Crick model for the structure of DNA
X-ray diffraction pattern of DNA
17
Complementarity of strands in the DNA double
helix
18
Replication of DNA as suggested by Watson and
Crick
19
DNA can occur in different three-dimensional forms
Structural variations in DNA
20
Comparison of A, B, and Z forms of DNA
21
Certain DNA sequences adopt unusual structures
22
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23
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24
DNA structures containing three or four DNA
strands
Hoogsteen pairing
25
Messenger RNAs code for polypeptide chains
Messenger RNA is only one of several classes of
cellular RNA
26
The product of transcription of DNA is always
single-stranded RNA. The single strand tends to
assume a right-handed helical conformation
dominated by base-stacking interactions.
Bases P atoms Riboses and phosphate oxygens
27
Secondary structure of RNAs
28
Base-paired helical structures in an RNA
Non Watson-Crick base pairs
Complementary sequences that may be paired in the
3D structure
29
Three-dimensional structure in RNA
Some unusual base-pairing patters found in this
tRNA
Phenylalanine tRNA of yeast
A hammerhead ribozyme from a plant virus
An intron (segment of mRNA) from the ciliated
protozoan Tetrahymena thermophila
30
Double-helical DNA and RNA can be denatured
Reversible denaturation and annealing
(renaturation) of DNA
31
Heat denaturation of DNA
32
Partially denatured DNA
Bubbles Regions rich in AT base pairs
specifically denature, while most DNA remains
double-stranded
33
Nucleic acids from different species can form
hybrids
DNA hybridization
Can be used to detect similar DNA sequences in
two different species or within the genome of a
single species
34
Nucleotides and nucleic acids undergo
nonenzymatic transformations
In DNA, uracil residues are removed by the
repair system
100 per day per cell
10,000 per day per cell
1 per day per cell
35
Formation of pyrimidine dimers induced by UV
light
36
Alkylating agents can alter certain bases of DNA
Cannot base-pair with cytosine
37
Chemical agents that cause DNA damage
Deaminating agents
38
The sequences of long DNA strands can be
determined
DNA sequencing by the Sanger method
39
Strategy for automating DNA sequencing reactions
40
dimethoxytrityl
The chemical synthesis of DNA has been automated
41
Nucleotides carry chemical energy in
cells. Adenine nucleotides are components of
many enzyme cofactors. Some nucleotides are
regulatory molecules.
Other functions of nucleotides
Nucleoside phosphates
42
The phosphate ester and phosphoanhydride bonds of
ATP
43
Some coenzymes containing adenosine
44
Three regulatory nucleotides
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