MacromolecularStructure

Hierarchyofstructuralorganization
Emergentpropertiesofmacromolecules
Structureandfunction
Biologicalmacromoleculesarepolymersmadeby
linkingmonomerstogetherinachain
Carbohydrates
Lipids
Proteins
NucleicAcids

Fig. 5-2
Synthesis and
Breakdown of
Polymers

HO

HO

Unlinked monomer

Short polymer
Dehydration removes a water
molecule, forming a new bond

HO

H2O

Longer polymer
(a) Dehydration reaction in the synthesis of a polymer

HO

Hydrolysis adds a water

molecule, breaking a bond

HO

(b) Hydrolysis of a polymer

H2O

HO

Figure 5.3

Aldoses (Aldehyde Sugars)

Ketoses (Ketone Sugars)

Trioses: 3-carbon sugars (C3H6O3)

Glyceraldehyde

Dihydroxyacetone

Pentoses: 5-carbon sugars (C5H10O5)

Ribose

Ribulose

Hexoses: 6-carbon sugars (C6H12O6)

Glucose

Galactose

Fructose

CarbohydrateRingStructure

Figure 5.5 Examples of disaccharide synthesis

Polysaccharides

Figure 5.6 Storage polysaccharides

Figure 5.8 The arrangement of cellulose in plant cell walls

Figure5.9Cellulosedigestingbacteriaare
foundingrazinganimalssuchasthiscow

Figure5.10Chitin,astructural
polysaccharide
CH2O
H
O OH
H
H
OH H
OH
H
H

NH
C O
CH
3

(a) The structure of the (b) Chitin forms the exoskeleton

of arthropods. This cicada
chitin monomer.
is molting, shedding its old
exoskeleton and emerging
in adult form.

(c) Chitin is used to make a

strong and flexible surgical
thread that decomposes after
the wound or incision heals.

Figure5.11Thesynthesisandstructure
ofafat,ortriacylglycerol
H
H

OH

OH

OH

H
C

HO

C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

H
C
H

Fatty acid
(palmitic acid)

Glycerol
(a) Dehydration reaction in the synthesis of a fat
Ester linkage
O

H
H

H
C
H

O
H

H
C
H

O
H

C
H

H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

(b) Fat molecule (triacylglycerol)

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C
H
H
C
H
H
C
H

H
C

H
H
C

H
H
C
H

H
C
H

Saturatedvs.UnsaturatedFat

Phospholipids

MembraneFormationby
Phospholipids
WATER
Hydrophilic
head

WATER
Hydrophobic
tail

Cholesterol:ASteroid

Figure 5.15-a

Enzymatic proteins

Defensive proteins

Function: Selective acceleration of chemical reactions

Example: Digestive enzymes catalyze the hydrolysis
of bonds in food molecules.

Function: Protection against disease

Example: Antibodies inactivate and help destroy
viruses and bacteria.
Antibodies

Enzyme

Virus

Bacterium

Storage proteins

Transport proteins

Function: Storage of amino acids

Examples: Casein, the protein of milk, is the major
source of amino acids for baby mammals. Plants have
storage proteins in their seeds. Ovalbumin is the
protein of egg white, used as an amino acid source
for the developing embryo.

Function: Transport of substances

Examples: Hemoglobin, the iron-containing protein of
vertebrate blood, transports oxygen from the lungs to
other parts of the body. Other proteins transport
molecules across cell membranes.
Transport
protein

Ovalbumin

Amino acids
for embryo

Cell membrane

Figure 5.15-b

Hormonal proteins

Receptor proteins

Function: Coordination of an organisms activities

Example: Insulin, a hormone secreted by the
pancreas, causes other tissues to take up glucose,
thus regulating blood sugar concentration

Function: Response of cell to chemical stimuli

Example: Receptors built into the membrane of a
nerve cell detect signaling molecules released by
other nerve cells.

High
blood sugar

Insulin
secreted

Normal
blood sugar

Receptor
protein

Signaling
molecules

Contractile and motor proteins

Structural proteins

Function: Movement
Examples: Motor proteins are responsible for the
undulations of cilia and flagella. Actin and myosin
proteins are responsible for the contraction of
muscles.

Function: Support
Examples: Keratin is the protein of hair, horns,
feathers, and other skin appendages. Insects and
spiders use silk fibers to make their cocoons and webs,
respectively. Collagen and elastin proteins provide a
fibrous framework in animal connective tissues.

Actin

Myosin
Collagen

Muscle tissue

100 m

Connective
tissue

60 m

Fig. 5-UN1

carbon

Amino
group

Carboxyl
group

Figure5.17The20aminoacidsof
proteins
CH3
CH3
H
H3 N+

CH3

O
H3 N+

H
Glycine (Gly)

H3 N+

H
Alanine (Ala)

CH2

O
H3N+

H
Valine (Val)

CH2

CH

CH3
CH3

CH3

CH3

H3 N+

H
Leucine (Leu)

H3 C

CH
C

O
C

H
Isoleucine (Ile)

Nonpolar

CH3

CH2

S
NH

CH2
CH2
H3 N+

C
H

CH2

O
H3 N+

C
O

Methionine (Met)

C
H

CH2

O
H3 N+

C
O

Phenylalanine (Phe)

C
H

H2 C

CH2

H2 N

O
C

C
O

Tryptophan (Trp)

Proline (Pro)

Figure5.17The20aminoacidsof
proteins
OH

OH

Polar

CH2
H3 N

CH

O
H3 N+

C
O

Serine (Ser)

CH2

O
H3 N+

C
O

CH2

O
C

H3 N+

CH2

O
H3 N

Electrically
charged

H3N+

NH3+

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

CH2

O
O

H3 N+

O
C

H3N+

C
H

Aspartic acid
(Asp)

O
C
O

Glutamine
(Gln)

NH2

H3 N

CH2

Basic
O

CH2

Asparagine
(Asn)

Acidic

Tyrosine
(Tyr)

Cysteine
(Cys)

Threonine (Thr)

NH2 O
C

SH

CH3

OH

NH2 O

Glutamic acid
(Glu)

O
C

NH2+

Lysine (Lys)

H3 N+

C
H

NH
CH2
H3 N+

C
H

CH2
O

NH+

C
O

O
C
O

Arginine (Arg)

Histidine (His)

PeptideBond
Formation

Figure5.19Conformationofaprotein,theenzyme
lysozyme

Groove

(a) A ribbon model

Groove

(b) A space-filling model

Figure 5.19

Antibody protein

Protein from flu virus

Figure5.21Levelsofprotein
structure
pleated sheet

1
Gly Pro ThrGly
5
Thr

H3N
Amino end
+

15

Met
Val
Lya
Val
Leu

Gly

Leu

Seu
Pro Cya Lya

Amino acid
subunits

Glu

10

helix

20
Asp

Ala Val Arg

Gly

O H
H
O HH
O H H
H R O
H
R
R
C
C H
C CN
C CH
C C N C N CC N
CC N C
C C
R
R
R
R
OH H
OH H
O
O HH
R
R
R
R
O
C H O C H O C H O C H
H
H
H
N
N
N
N
C
C
C
C HC N C H N C H N C
H
C
H O C
H O C
C
H O C
H ON
R
R
R
R H
R H
C
C
O C N H
O C
N H
N H
N H
O C
O C
H
RH
C
R
C
H C
H C
R
R
N HO C
N HO C
O C N H
O C N H
C
C
R N
R H
C N
H

Ser

Pro
Ala

25

Figure5.21ExploringLevelsofProtein
Structure:Primarystructure
H3N
Amino end

Gly Pro Thr Gly

Thr

Amino acid
subunits

Gly

Leu
Met
Val

Seu
Pro Cys Lys

Glu

Lys
Val
Leu

Asp

Ala Val Arg Gly

Glu Lle
Asp

Ser
Pro
Ala

Thr
Lys
Ser

Gly

Lys Trp Tyr

Leu Ala

lle
Ser

Pro Phe

His Glu
His
Ala
Glu

Asn

Ala Thr Phe Val

Asp
Ser

Gly Pro

Thr

Arg

Arg

Val

Tyr

Thr

lle
Ala
Ala
Leu

Ser
Ser Tyr

Tyr Pro

Leu
Ser

Thr
Ala
Val
Val

Thr

Asn Pro

Lys Glu

o
o

Carboxyl end

Fig. 5-22
Normal hemoglobin
Primary
structure

Secondary
and tertiary
structures

subunit

Function

Normal
hemoglobin
(top view)

Secondary
and tertiary
structures

Val His Leu Thr Pro Val Glu

Function

Molecules do
not associate
with one
another; each
carries oxygen.

Sickle-cell
hemoglobin

Normal red blood

cells are full of
individual
hemoglobin
moledules, each
carrying oxygen.

Molecules
interact with
one another and
crystallize into
a fiber; capacity
to carry oxygen
is greatly reduced.

10 m
Red blood
cell shape

subunit

Exposed
hydrophobic
region

Quaternary
structure

Sickle-cell hemoglobin

Quaternary
structure

Primary
structure

Val His Leu Thr Pro Glu Glu

10 m
Red blood
cell shape

Fibers of abnormal
hemoglobin deform
red blood cell into
sickle shape.

Figure5.21ExploringLevelsofProteinStructure:
Secondarystructure
pleated sheet
H

Amino acid
subunits

C
N

N
C

N
O

N
O

O
C

C
R

H C
O

C
H

C
H

H
C

O
N
H

C
R

C
H

helix

N
H

R
C

N
C

N
C

H C
O

O
H

N
C
R

C
N
H

R
R

C
N

R
O

H
C
O

O
H

N
C
R

C
N
H

H C
O

N
C

Figure5.21ExploringLevelsofProtein
Structure:Tertiarystructure

CH2

Hydrogen
bond

H3C

CH

CH3
H3C
CH3
CH

O
H
O

Hydrophobic
interactions and
van der Waals
interactions

OH C
CH2

CH2 S S CH2
Disulfide bridge

O
CH2 NH3+ -O C CH2
Ionic bond

Polypeptide
backbone

ProteinQuaternaryStructure

Figure 5.23 Denaturation and renaturation of a protein

Figure5.26DNARNAprotein:a
diagrammaticoverviewofinformationflowina
cell
DNA

1 Synthesis of
mRNA in the nucleus

mRNA

NUCLEUS
CYTOPLASM
mRNA
2 Movement of
mRNA into cytoplasm
via nuclear pore

Ribosome

3 Synthesis
of protein

Polypeptide

Amino
acids

Figure5.27Thecomponentsofnucleicacids
Nitrogenous bases
Pyrimidines

5 end
5C

NH2

3C
Nucleoside
O

5C

3C

Nitrogenous
base
O

O P O

O
C

CH3
C
HN
C
HN
CH
C
CH
C
CH
N
N
O
N
O
O
H
H
H
Cytosine Thymine (in DNA) Uracil (in RNA)
C
U
T
N
C

CH
CH

5C
CH2 O

Purines
NH2

O
Phosphate 3C
Pentose
group
sugar

HC

N C C
N

CH
N C
N
H
Adenine
A

(b) Nucleotide

OH
3 end
(a) Polynucleotide,
or nucleic acid

N
HC

OH

HOCH2 O
H

NH
C

NH2

HOCH2 O OH

H 3 2 H
OH H
Deoxyribose (in DNA)

N C N
H
Guanine
G

Pentose sugars

H 3 2 H
OH OH
Ribose (in RNA)

(c) Nucleoside components

Figure5.28TheDNAdoublehelixanditsreplication
3 end

5 end
G

Sugar-phosphate
backbone

T
C

Base pair (joined

by
hydrogen bonding)
Old strands

G
A

T
A

A
A

Nucleotide
about to be
added to a
new strand

C
G

3 end
G

A
C

5 end

5 end

3 end

New
strands

G
A

3 end

A
T

5 end