Chapter 5

The Structure and Function of

Macromolecules

PowerPoint Lectures for

Biology, Seventh Edition
Neil Campbell and Jane Reece

Lectures by Chris Romero

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 • Overview: The Molecules of Life
– Another level in the hierarchy of biological
organization is reached when small organic
molecules are joined together

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 • Macromolecules
– Are large molecules composed of smaller
molecules
– Are complex in their structures

Figure 5.1

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 Concept 5.1: Most macromolecules are
polymers, built from monomers
• Three of the classes of life’s organic
molecules are polymers
– Carbohydrates
– Proteins
– Nucleic acids

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 • A polymer
– Is a long molecule consisting of many similar
building blocks called monomers

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 The Synthesis and Breakdown of Polymers
• Monomers form larger molecules by
condensation reactions called dehydration
reactions

HO 1 2 3 H HO H

Short polymer Unlinked monomer

Dehydration removes a water

H2O
molecule, forming a new bond

HO 1 2 3 4 H
Longer polymer
Figure 5.2A (a) Dehydration reaction in the synthesis of a polymer

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 • Polymers can disassemble by
– Hydrolysis

HO 1 2 3 4 H

Hydrolysis adds a water

H2O
molecule, breaking a bond

HO 1 2 3 H HO H

Figure 5.2B (b) Hydrolysis of a polymer

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 The Diversity of Polymers
• Each class of polymer
– Is formed from a specific set of monomers
1 2 3 H HO

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 • Although organisms share the same limited
number of monomer types, each organism is
unique based on the arrangement of
monomers into polymers
• An immense variety of polymers can be built
from a small set of monomers

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 • Concept 5.2: Carbohydrates serve as fuel and
building material
• Carbohydrates
– Include both sugars and their polymers

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 Sugars
• Monosaccharides
– Are the simplest sugars
– Can be used for fuel
– Can be converted into other organic molecules
– Can be combined into polymers

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 • Examples of monosaccharides
Triose sugars Pentose sugars Hexose sugars
(C3H6O3) (C5H10O5) (C6H12O6)
H O H O H O H O
C C C C
H C OH H C OH H C OH H C OH

Aldoses
H C OH H C OH HO C H HO C H
H H C OH H C OH HO C H
H C OH H C OH H C OH
Glyceraldehyde
H H C OH H C OH
Ribose H H
Glucose Galactose

H H H
H C OH H C OH H C OH
C O C O C O
Ketoses

H C OH H C OH HO C H

H H C OH H C OH
Dihydroxyacetone H C OH H C OH

H H C OH
Ribulose H
Figure 5.3 Fructose

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 • Monosaccharides
– May be linear
– Can form rings
H O
1C 6
CH2OH 6
CH2OH
2
CH2OH
H C OH 5C O H 5
C O 6
3 H H H H H O
HO C H
5 H
4 H 1 4 H 1 H
4 C C C C 4 1
OH H OH H OH
H C OH O 3 2
HO OH
5 OH 2 OH 3 2 OH
3 C C C C
H C OH
H OH
6 H OH H OH
H C OH

H
(a) Linear and ring forms. Chemical equilibrium between the linear and
Figure 5.4 ring
structures greatly favors the formation of rings. To form the glucose ring,
carbon 1 bonds to the oxygen attached to carbon 5.

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 • Disaccharides
– Consist of two monosaccharides
– Are joined by a glycosidic linkage

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 • Examples of disaccharides
(a) Dehydration reaction
in the synthesis of
maltose. The bonding CH2OH CH2OH CH2OH CH2OH
of two glucose units O O O O
forms maltose. The H H H H H H 1– 4 H H
H H H 1 glycosidic 4 H
glycosidic link joins
OH H OH H OH H linkage OH H
OHOH
the number 1 carbon OH HO
of one glucose to the HO HO O OH
number 4 carbon of
the second glucose. H OH H OH H OH H OH
Joining the glucose H2O
monomers in a Glucose Maltose
Glucose
different way would
result in a different
disaccharide.
CH2OH CH2OH
CH2OH CH2OH
H O O H O H 1–2 O
H H H
H H 1 glycosidic 2
(b) Dehydration reaction OH H H HO OH H linkage H HO
OH HO
in the synthesis of HO CH2OH HO O CH2OH
sucrose. Sucrose is
a disaccharide formed H OH OH H H OH OH H
from glucose and fructose.
Notice that fructose,
H2O
though a hexose like Glucose Fructose Sucrose
glucose, forms a
five-sided ring.

Figure 5.5

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 Polysaccharides
• Polysaccharides
– Are polymers of sugars
– Serve many roles in organisms

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 Storage Polysaccharides
• Starch
– Is a polymer consisting entirely of glucose
monomers

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 – Is the major storage form of glucose in plants
Chloroplast Starch

1 μm

Amylose Amylopectin

Figure 5.6 (a) Starch: a plant polysaccharide

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 • Glycogen
– Consists of glucose monomers
– Is the major storage form of glucose in animals
Mitochondria Giycogen
granules

0.5 μm

Glycogen

Figure 5.6 (b) Glycogen: an animal polysaccharide

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 Structural Polysaccharides
• Cellulose
– Is a polymer of glucose

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 – Has different glycosidic linkages than starch
H O
CH2O C CH2O
H H
O H C OH H O OH
H H
H H
4
OH H HO C H 4 1
OH H
HO OH HO H
H C OH
H OH C H OH
H OH
α glucose H C OH β glucose

(a) α and β glucose ring structures

CH2O CH2O CH2O CH2O

H H H H
O O O O
1 4 1 4 1 4 1
OH OH O OH O OH O
HO O

OH OH OH OH
(b) Starch: 1– 4 linkage of α glucose monomers
CH2O CH2O
OH OH
H H
O O
O OH O OH
OH 1 4 O OH
HO OH
O O
CH2O CH2O
OH OH
(c) Cellulose: 1– 4Hlinkage of β glucose H
Figure 5.7 A–C monomers

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 – Is a major component of the tough walls that
enclose plant cells
About 80 cellulose
Cellulose microfibrils molecules associate
in a plant cell wall Microfibril to form a microfibril, the
Cell walls main architectural unit

∩
of the plant cell wall.

0.5 μm

Plant cells

CH2OH OH CH2OH OH
O O O O
OH OH OH OH
O O O O O
OH CH2OH OH CH2OH Cellulose
CH2OH OH CH2OH OH molecules
O O O O
OH OH OH OH
Parallel cellulose molecules are O O O O O
held together by hydrogen OH CH2
OH OH CH2
OH
bonds between hydroxyl CH2OH OH CH2OH OH
O O O O
groups attached to carbon OH OH
O OH O O
OH O
atoms 3 and 6. O A cellulose molecule
OH CH2OH OH CH OH
2 is an unbranched β
Figure 5.8 β Glucose glucose polymer.
monomer
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 • Cellulose is difficult to digest
– Cows have microbes in their stomachs to
facilitate this process

Figure 5.9

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 • Chitin, another important structural
polysaccharide
– Is found in the exoskeleton of arthropods
– Can be used as surgical thread
CH2O
H
H O OH
H
OH H
OH H
H NH
C O
CH3

(a) The structure of the (b) Chitin forms the exoskeleton (c) Chitin is used to make a
chitin monomer. of arthropods. This cicada strong and flexible surgical
is molting, shedding its old thread that decomposes after
exoskeleton and emerging the wound or incision heals.
Figure 5.10 A–C in adult form.

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 • Concept 5.3: Lipids are a diverse group of
hydrophobic molecules
• Lipids
– Are the one class of large biological molecules
that do not consist of polymers
– Share the common trait of being hydrophobic
– Most important lipids to biology: fats,
phospholipids and steroids

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 Fats
• Fats
– Are constructed from two types of smaller
molecules, a single glycerol and usually three
fatty acids

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 • Fatty acids
– Vary in the length and number and locations of
double bonds they contain

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 • Saturated fatty acids
– Have the maximum number of hydrogen atoms
possible
– Have no double bonds

Stearic acid

Figure 5.12 (a) Saturated fat and fatty acid

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 • Unsaturated fatty acids
– Have one or more double bonds

Oleic acid

cis double bond

Figure 5.12 (b) Unsaturated fat and fatty acid causes bending

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 Phospholipids
• Phospholipids
– Have only two fatty acids
– Have a phosphate group instead of a third
fatty acid

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 • Phospholipid structure
– Consists of a hydrophilic “head” and
hydrophobic “tails”
+
Hydrophilic head

CH2 N(CH )
3 3 Choline
CH2
O
O P O–
Phosphate
O
CH2 CH CH2
Glycerol
O O
C O C O

Fatty acids
Hydrophobic tails

Hydrophilic
head
Hydrophobic
tails

(c) Phospholipid
(a) Structural formula (b) Space-filling model
Figure 5.13 symbol
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 • The structure of phospholipids
– Results in a bilayer arrangement found in cell
membranes
WATER
Hydrophilic
head

WATER
Hydrophobic
tail
Figure 5.14

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 Steroids
• Steroids
– Are lipids characterized by a carbon skeleton
consisting of four fused rings

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 • One steroid, cholesterol
– Is found in cell membranes
– Is a precursor for some hormones

H3C CH3

CH3 CH3

CH3

Figure 5.15 HO

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 • Concept 5.4: Proteins have many structures,
resulting in a wide range of functions
– Proteins
• Have many roles inside the cell

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 • An overview of protein functions

Table 5.1

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Copyright © 2005 Pearson Education, Inc. publishing as Benjamin Cummings
 • Enzymes
– Are a type of protein that acts as a catalyst,
speeding up chemical reactions
1 Active site is available for 2 Substrate binds to
a molecule of substrate, the enzyme.
Substrate
reactant on which the enzyme acts. (sucrose)

Glucose
Enzyme
OH (sucrase)
H2O
Fructose

H O

4 Products are released. 3 Substrate is converted

Figure 5.16 to products.
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 Polypeptides
• Polypeptides
– Are polymers of amino acids
• A protein
– Consists of one or more polypeptides

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 Amino Acid Monomers
• Amino acids
– Are organic molecules possessing both
carboxyl and amino groups
– Differ in their properties due to differing side
chains, called R groups

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 • 20 different amino acids make up proteins

CH3
CH3 CH3

CH3 CH3 CH CH2

H CH3 CH3 CH2 H3C CH
O O O O O
+ + + +
H3N C C H3N C C H3N C C H3N C C H3N + C C
O –
O – O –
O – O–
H H H H H
Glycine (Gly) Alanine (Ala) Valine (Val) Leucine (Leu) Isoleucine (Ile)
Nonpolar

CH3
CH2
S
H2C CH2 O
NH
CH2
H2N C C
CH2 O CH2 CH2 O–
O O H
H3N+ C C H3N+ C C H3N+ C C
O– O– O–
H H H
Methionine (Met) Phenylalanine (Phe) Tryptophan (Trp) Proline (Pro)

Figure 5.17

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 OH NH2 O
NH2 O C
OH SH C CH2
Polar OH CH3
CH2 CH CH2 CH2 CH2 O CH2
O O O O O
+ + + + +
H3N C C H3N C C H3N C C H3N +
C C H3N C C H3N C C
O– O– O– O– O– O–
H H H H H H
Cysteine Tyrosine Asparagine Glutamine
Serine (Ser) Threonine (Thr) (Gln)
(Cys) (Tyr) (Asn)

Acidic Basic

NH3+ NH2 NH+

–
O O O– O
C C CH2 C NH2+
NH
Electrically CH2
CH2 O CH2 CH2 CH2
charged O
H3N +
C C CH2 CH2 CH2 H3N+ C C
–
O
O CH2 O–
H3N+ C C O CH2 H
H –
O +
H H3N C C CH2
–
O
O
H H3N+ C C
O–
H
Aspartic acid Glutamic acid Lysine (Lys) Arginine (Arg) Histidine (His)
(Asp) (Glu)

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 Amino Acid Polymers
• Amino acids
– Are linked by peptide bonds
OH
Peptide
bond
OH SH
CH2 CH2 CH2
H H H
N
H C C N C C OH H N C C OH
H O H O H O DESMOSOMES
(a) H2O

OH
DESMOSOMES
DESMOSOMES Side
OH SH
Peptide chains
CH2 CH2 bond CH2
H H H
H N C C N C C N C C OH Backbone
H O H O H O

Amino end Carboxyl end

Figure 5.18 (b) (N-terminus) (C-terminus)

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 Determining the Amino Acid Sequence of a Polypeptide
• The amino acid sequences of polypeptides
– Were first determined using chemical means
– Can now be determined by automated
machines

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 Protein Conformation and Function
• A protein’s specific conformation
– Determines how it functions

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 Four Levels of Protein Structure
• Primary structure
– Is the unique sequence of amino acids in a
polypeptide HN Amino acid
+
3
Gly ProThr Gly
Thr
Gly

Amino LeuPro
CysLysSeu
Glu
subunits
end Met
Val
Lys
Val
Leu
Asp
Ala Val Arg Gly
Ser
Pro
Ala

Glu Lle
Asp
Thr
Lys
Ser
Lys Trp Tyr
Leu Ala
Gly
lle
Ser
ProPheHis
Glu His
Ala
Glu
Val
Ala Thr PheVal
Asn
lle
Thr
Asp Tyr Ala
Arg
Ser Arg Ala
Gly Pro
Leu
Leu
Ser
Pro
SerTyr
Tyr
ThrSer
Thr
Ala
Val o
Val
ThrAsnProLys
Glu c –
o

Figure 5.20 Carboxyl end

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Copyright © 2005 Pearson Education, Inc. publishing as Benjamin Cummings
 • Secondary structure
– Is the folding or coiling of the polypeptide into a
repeating configuration
– Includes the α helix and the β pleated sheet
β pleated sheet
O H H O H H O H H O H H
R R R
Amino acid C C N C C N C C N C C N
C N C C N C C N C C N C C
subunits R R R R
H O H H OH H OH H O

R R R R
O C O O C O H
C H H H C
H C N HC H H
C N HC N N C NH C N C N HC N
H H C H O C H
C O C O O C
R R R
R H R H
C C
N H O C N H O C
N H N H
O C O C α helix
H C R H C H C R H C R
R
N H O C N H
O C
O C N H O C N H
C C
R H R H

Figure 5.20
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 • Tertiary structure
– Is the overall three-dimensional shape of a
polypeptide
– Results from interactions between amino acids
and R groups
Hydrophobic
interactions and
CH van der Waals
CH2
CH 2 H3C CH3 interactions
O
Hyrdogen H H3C CH3 Polypeptide
bond O CH backbone
HO C
CH2 CH2 S S CH2
Disulfide bridge
O
CH2 NH3+ -O C CH2
Ionic bond

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Copyright © 2005 Pearson Education, Inc. publishing as Benjamin Cummings
 • Quaternary structure
– Is the overall protein structure that results from
the aggregation of two or more polypeptide
subunits

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 • The four levels of protein structure

+
H3N
Amino end

Amino acid
subunits
α helix

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 Sickle-Cell Disease: A Simple Change in
Primary Structure

• Sickle-cell disease
– Results from a single amino acid substitution in
the protein hemoglobin

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 • Hemoglobin structure and sickle-cell disease

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 What Determines Protein Conformation?
• Protein conformation
– Depends on the physical and chemical
conditions of the protein’s environment

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 • Denaturation
– Is when a protein unravels and loses its native
conformation
Denaturation

Normal protein Denatured protein

Figure 5.22 Renaturation

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 The Protein-Folding Problem
• Most proteins
– Probably go through several intermediate
states on their way to a stable conformation

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 • Chaperonins
– Are protein molecules that assist in the proper
folding of other proteins
Correctly
folded
Polypeptide
protein
Cap

Hollow
cylinder

Chaperonin Steps of Chaperonin 2 The cap attaches, causing 3 The cap comes
(fully assembled) Action: the cylinder to change shape in off, and the properly
1 An unfolded poly- such a way that it creates a folded protein is
peptide enters the hydrophilic environment for the released.
Figure 5.23 cylinder from one end. folding of the polypeptide.

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 • X-ray crystallography
– Is used to determine a protein’s
three-dimensional structure X-ray
diffraction
pattern
Photographic film
Diffracted X-rays
X-ray X-ray
source beam

Crystal Nucleic acid Protein

Figure 5.24 (a) X-ray diffraction pattern (b) 3D computer model

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 • Concept 5.5: Nucleic acids store and transmit
hereditary information
• Genes
– Are the units of inheritance
– Program the amino acid sequence of
polypeptides
– Are made of nucleic acids

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 The Roles of Nucleic Acids
• There are two types of nucleic acids
– Deoxyribonucleic acid (DNA)
– Ribonucleic acid (RNA)

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 • DNA
– Stores information for the synthesis of specific
proteins

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 – Directs RNA synthesis
– Directs protein synthesis through RNA
DNA

1 Synthesis of
mRNA in the nucleus mRNA

NUCLEUS
CYTOPLASM

mRNA
2 Movement of
mRNA into cytoplasm Ribosome
via nuclear pore

3 Synthesis
of protein

Amino
Figure 5.25 Polypeptide acids

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 The Structure of Nucleic Acids
• Nucleic acids
– Exist as polymers called polynucleotides

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 • Each polynucleotide
– Consists of monomers called nucleotides

Nucleoside

Nitrogenous
base

O 5’C
−
O P O CH2
O
O−
Phosphate
3’C
group Pentose
sugar

Figure 5.26 (b) Nucleotide

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 Nucleotide Monomers
• Nucleotide monomers
– Are made up of nucleosides and phosphate
groups Nitrogenous bases
Pyrimidines
NH2 O O
C C CH3 C
N CH HN C HN CH
C CH C CH C CH
O N O N O N
H H H
Cytosine Thymine (in DNA) Uracil (in RNA)
Uracil (in RNA)
C T UU

Purines
NH2 O
N CC N C C
N NH
HC HC
N C CH N C
N N NH2
H H
Adenine Guanine
A G

Pentose sugars
5” 5”
HOCH2 O OH HOCH2 O OH
4’ H H 1’ 4’ H H 1’

H 3’ 2’ H H H
3’ 2’
OH H OH OH
Deoxyribose (in DNA) Ribose (in RNA)

Figure 5.26 (c) Nucleoside components

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 Nucleotide Polymers
• Nucleotide polymers
– Are made up of nucleotides linked by the–OH
group on the 3´ carbon of one nucleotide and
the phosphate on the 5´ carbon on the next

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 • The sequence of bases along a nucleotide
polymer
– Is unique for each gene

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 The DNA Double Helix
• Cellular DNA molecules
– Have two polynucleotides that spiral around an
imaginary axis
– Form a double helix

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 • The DNA double helix
– Consists of two antiparallel nucleotide strands
5’ end 3’ end

Sugar-phosphate
backbone
Base pair (joined by
hydrogen bonding)
Old strands

Nucleotide
about to be
added to a
new strand
A 3’ end

5’ end

3’ end New
strands

Figure 5.27 5’ end 3’ end

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 • The nitrogenous bases in DNA
– Form hydrogen bonds in a complementary
fashion (A with T only, and C with G only)

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 DNA and Proteins as Tape Measures of Evolution
• Molecular comparisons
– Help biologists sort out the evolutionary
connections among species

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 The Theme of Emergent Properties in the
Chemistry of Life: A Review

• Higher levels of organization

– Result in the emergence of new properties
• Organization
– Is the key to the chemistry of life

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