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 lifes 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

HO

Short polymer

Unlinked monomer
H2O

Dehydration removes a water molecule, forming a new bond

HO Figure 5.2A 1 2 3 4

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

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 Polymers can disassemble by

Hydrolysis

HO

Hydrolysis adds a water molecule, breaking a bond

H2O

HO

HO

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

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 (C3H6O3) (C5H10O5)
H C H C OH H H H H O H C C C C C H OH OH OH OH H HO H H H O H C C C C C C H OH H OH OH OH H HO HO H H

Hexose sugars (C6H12O6)

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

Aldoses

C
H

OH

Glyceraldehyde

Ribose

Glucose
H H C OH C O H H H H H H

Galactose

C OH C O

C OH C O

Ketoses

C OH H

C OH C OH C OH H

HO H H H

C H C OH C OH C OH H

Dihydroxyacetone

Ribulose

Figure 5.3

Fructose

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 Monosaccharides
May be linear

Can form rings

H
1C 2 3 4

O
6CH OH 2 6CH OH 2

H HO H H

C C

OH

5C

H
H OH
4C

H H H
4C
1C

5C

O
1C

CH2OH
H
6

H
4

O
1 2

C
5

H OH
3

H OH

H
2C

OH
C OH

H OH
3C

H
2C

H OH
3

OH

HO
OH

OH

C
H

OH

OH

OH

Figure 5.4 (a) Linear and ring forms. Chemical equilibrium between the linear and 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 of two glucose units forms maltose. The glycosidic link joins the number 1 carbon of one glucose to the number 4 carbon of the second glucose. Joining the glucose monomers in a different way would result in a different disaccharide.

CH2OH
H HO H O H OH H H OH H

CH2OH O H OH H H2O H OH

CH2OH

CH2OH H
1 4 1 glycosidic linkage

H
OH OH

H HO

O H OH H H OH

H
4

O H OH H H OH

HO

OH

OH

Glucose

Glucose

Maltose

CH2OH H
(b) Dehydration reaction in the synthesis of HO sucrose. Sucrose is a disaccharide formed from glucose and fructose. Notice that fructose, though a hexose like glucose, forms a five-sided ring.

O H OH H H

CH2OH H OH HO H

CH2OH O HO CH2OH HO H OH
Sucrose

O H OH H

12 glycosidic 1 linkage

CH2OH O
2

HO

O OH H

CH2OH

OH H2O

OH

Glucose

Fructose

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 m

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 m

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 CH2O H O H OH H H OH C H OH H HO H H H C C C OH H OH OH OH O CH2O H H O OH H 4 1 OH H HO H H OH H
4

HO

C
C

glucose

glucose

(a) and glucose ring structures CH2O H O HO OH OH CH2O H O

1 4

CH2O H O O OH OH
1 4

CH2O H O O OH OH
1

CH2O H O O
4

OH OH

(b) Starch: 1 4 linkage of glucose monomers OH O

1

CH2O H O O OH O OH

OH

HO

OH

OH

Figure 5.7 AC

O O CH2O CH2O OH OH H H (c) Cellulose: 1 4 linkage of glucose monomers

OH

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 Is a major component of the tough walls that enclose plant cells

Cell walls Cellulose microfibrils in a plant cell wall Microfibril About 80 cellulose molecules associate to form a microfibril, the main architectural unit of the plant cell wall.

0.5 m

Plant cells

Parallel cellulose molecules are held together by hydrogen bonds between hydroxyl groups attached to carbon atoms 3 and 6.

Figure 5.8

OH CH2OH OH CH2OH O O O O OH OH OH OH O O O O O O CH OH OH CH2OH 2 H CH2OH OH CH2OH OH O O O O OH OH OH O OH O O O O O CH OH OH CH2OH 2 H CH2OH OH OH CH2OH O O O O OH OH OH O O OH O O O O CH OH OH CH2OH 2 H

Cellulose molecules

Glucose
monomer

A cellulose molecule is an unbranched glucose polymer.

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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 O OH H H OH H OH H H

NH
C
CH3

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

 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

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Fats Fats
Are constructed from two types of smaller molecules, a single glycerol and usually three fatty acids
H H H H O OH HO OH OH C

C
C 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 C H

H C

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

H H C O O C H C H C H H C H H C H H C H H C H H C H

H C
H

H C

H C
H

H C H H C

H C H H C H H C H

H C

H C H H C H H C H

H C

H C H H C H H C H

H C H H C

H C H H C H H C H

H C H H C

H
O H C

H
H C H H C H

H
H C

H
H C

H C H

H C
H H C H

H C
H H C H

H
H C H

H
H C H

H
H C H

H
H C H

H
H C H H

O H C H O C

H C H

Figure 5.11

(b) Fat molecule (triacylglycerol)

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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

Figure 5.12

(b) Unsaturated fat and fatty acid

cis double bond 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
CH2 CH2 O CH2 O C CH O O C O O P O CH2 O

+ N(CH )

3 3

Choline

Phosphate
Glycerol

Fatty acids
Hydrophilic head Hydrophobic tails

Figure 5.13

(a) Structural formula

(b) Space-filling model

(c) Phospholipid 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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 Enzymes
Are a type of protein that acts as a catalyst, speeding up chemical reactions
1 Active site is available for a molecule of substrate, the reactant on which the enzyme acts.
Substrate (sucrose)

2 Substrate binds to enzyme.

Glucose OH Fructose H O Enzyme (sucrase) H2O

4 Products are released. Figure 5.16

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3 Substrate is converted to products.

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 H3 O N+ C C O O H3N+ CH CH2 C C O O H3C CH3 CH3 CH2 CH C C O H Isoleucine (Ile) O

H
H3N+ C C

O H3N+ O

CH3
C C

H3N+

H Glycine (Gly) Nonpolar

H Alanine (Ala)

H Valine (Val)

H Leucine (Leu)

CH3 S CH2 CH2 H3N+ C H C O O H3N+ CH2 O CH2 NH CH2

H2C
H2N

CH2 C H C

O O

C
H

C
O

H3N+

C
H

C
O Proline (Pro)

Methionine (Met)

Phenylalanine (Phe)

Tryptophan (Trp)

Figure 5.17
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OH NH2 O C O C O H3N+ CH2 C C O O H3N+ CH2 C H C O H3N+ O

NH2 O C CH2 CH2 C H C O O

Polar
H3N+

OH CH2 O C O

OH

CH3 CH O C O H3N+ C H

SH CH2 C H

C
H

H3N+

Serine (Ser)

Threonine (Thr)

Cysteine (Cys)

Tyrosine (Tyr)

Asparagine (Asn)

Glutamine (Gln)

Acidic
O

Basic
O C O NH3+ CH2 CH2 O C O H3N+ CH2 CH2 C H C O H3N+ O NH2 C CH2 CH2 CH2 CH2 O C O H3N+ NH2+ NH+ NH CH2 O C C O H

O C

Electrically charged
H3N+

CH2

O C O H3N+

CH2 CH2 C

C
H

C
H

Aspartic acid (Asp)

Glutamic acid (Glu)

Lysine (Lys)

Arginine (Arg)

Histidine (His)

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Amino Acid Polymers Amino acids

Are linked by peptide bonds
Peptide bond OH CH2 H H OH SH CH2 H C OH O DESMOSOMES H O H
H2O

CH2

(a) OH

DESMOSOMES DESMOSOMES
OH CH2 H H N C C H O Peptide CH2 bond CH2 SH

Figure 5.18

(b)

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C C
H O

N C C OH H N C

Side chains

H
N C C H O

H
N C C OH H O Backbone

Amino end (N-terminus)

Carboxyl end (C-terminus)

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 proteins specific conformation

Determines how it functions

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 Two models of protein conformation

Groove

(a) A ribbon model

Groove

Figure 5.19

(b) A space-filling model

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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 Pro Thr Gly Thr Gly

Amino end

Glu Cys LysSeu LeuPro Met Val Lys Val Leu Asp AlaVal Arg Gly Ser Pro Ala

subunits

Glu Lle

Asp Thr Lys

Leu Ala Gly lle Ser

Ser Lys Trp Tyr

ProPhe His Glu

His Ala

Ala Thr PheVal Asn

Glu Val Thr lle Ala Ala Leu

Asp Tyr Arg Ser Arg Gly Pro

Thr Ser Thr Ala

Tyr

Leu Ser Pro SerTyr

Val Val LysGlu Thr AsnPro

o o

Figure 5.20
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Carboxyl end

 Secondary structure
Is the folding or coiling of the polypeptide into a repeating configuration Includes the helix and the pleated sheet
pleated sheet
Amino acid subunits
C N H O H H C C N R R O C H O R

C C N O H H

O H H C C N R R

C C N OH H

O H H C C N R R O

C C N OH H

O H H C C N R R C C O

C H H H C N HC C N HC N C N H H C O C C O R R R C N H

O C H H NH C N C H O C R

H C N HC N H O C

R C

O C O C N H N H N H O C O C H C R H C R H C R H C R N H O C N H O C O C H C O N H N C C H R H R

helix

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
Hyrdogen bond
CH CH 22 O H O CH2 CH H3C CH3 H3C CH3 CH

interactions and van der Waals interactions Polypeptide backbone

HO C CH2 S S CH2

Disulfide bridge O
CH2 NH3+ -O C CH2 Ionic bond

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 Quaternary structure
Is the overall protein structure that results from the aggregation of two or more polypeptide subunits
Polypeptide chain

Collagen Chains

Iron Heme Chains Hemoglobin

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 The four levels of protein structure

+H N 3

Amino end Amino acid subunits

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

Primary structure Secondary and tertiary structures Quaternary Hemoglobin A structure Normal hemoglobin
Val His Leu Thr Pro Glul Glu

. . . Primary

Sickle-cell hemoglobin
Val His Leu Thr Pro Val Glu

...

1 2 3 4 5 6 7

structure 1 2 3 4 5 6 7

Secondary subunit and tertiary structures Quaternary structure Function

Exposed hydrophobic region

subunit

Hemoglobin S
Molecules interact with one another to crystallize into a fiber, capacity to carry oxygen is greatly reduced. Fibers of abnormal hemoglobin deform cell into sickle shape.

Function

Molecules do not associate with one another, each carries oxygen. Normal cells are full of individual hemoglobin molecules, each carrying oxygen

10 m Red blood cell shape

10 m

Red blood cell shape

Figure 5.21
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What Determines Protein Conformation? Protein conformation

Depends on the physical and chemical conditions of the proteins environment

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

Normal protein
Renaturation

Denatured protein

Figure 5.22

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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
Polypeptide Cap Correctly folded protein

Hollow cylinder

Chaperonin (fully assembled)

Figure 5.23

Steps of Chaperonin Action: 1 An unfolded polypeptide enters the cylinder from one end.

2 The cap attaches, causing

3 The cap comes

the cylinder to change shape in off, and the properly such a way that it creates a folded protein is hydrophilic environment for the released. folding of the polypeptide.

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 X-ray crystallography
Is used to determine a proteins threeX-ray dimensional structure diffraction
pattern

Photographic film
Diffracted X-rays X-ray X-ray beam source 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 via nuclear pore 3 Synthesis
of protein

Ribosome

Figure 5.25

Polypeptide

Amino acids

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The Structure of Nucleic Acids Nucleic acids

Exist as polymers called polynucleotides
5 end 5C 3C O

5C 3C OH

O 3 end

Figure 5.26

(a) Polynucleotide, or nucleic acid

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 Each polynucleotide
Consists of monomers called nucleotides
Nucleoside Nitrogenous base

5C O CH2 O

P O

Phosphate group

3C

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 CH C 3 N CH C CH HN HN CH C CH C C CH N N O N O O H H H Cytosine Thymine (in DNA) Uracil (in RNA) Uracil (in RNA) U C U T Purines O NH2 N C C N CC NH N HC HC C CH N C N NH2 N N H H Adenine Guanine A G
5

Pentose sugars HOCH2 O OH

4 5

HOCH2 O OH
4

H H

H H

H H H 3 2 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 theOH 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 3 end

Figure 5.27

5 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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