The Structure and Function of Macromolecules: Powerpoint Lectures For

Chapter 5
The Structure and Function of Macromolecules

PowerPoint Lectures for Biology, Seventh Edition
Neil Campbell and Jane Reece
Lectures by Chris Romero

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings
Overview: The Molecules of Life

Another level in the hierarchy of biological organization is reached when small organic molecules are joined together
Macromolecules
Are large molecules composed of smaller molecules Are complex in their structures
Figure 5.1
Concept 5.1: Most macromolecules are polymers, built from monomers Three of the classes of lifes organic molecules are polymers
Carbohydrates Proteins Nucleic acids
A polymer
Is a long molecule consisting of many similar building blocks called monomers
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
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
The Diversity of Polymers Each class of polymer

Is formed from a specific set of monomers
1 2
HO
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
Concept 5.2: Carbohydrates serve as fuel and building material Carbohydrates

Include both sugars and their polymers
Sugars Monosaccharides
Are the simplest sugars
Can be used for fuel

Can be converted into other organic molecules
Can be combined into polymers
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
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.
Disaccharides
Consist of two monosaccharides
Are joined by a glycosidic linkage
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
Polysaccharides Polysaccharides
Are polymers of sugars
Serve many roles in organisms
Storage Polysaccharides Starch

Is a polymer consisting entirely of glucose monomers
Is the major storage form of glucose in plants

Chloroplast Starch
1 m
Amylose
Amylopectin
Figure 5.6 (a) Starch: a plant polysaccharide

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

Structural Polysaccharides Cellulose

Is a polymer of glucose
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
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.
Cellulose is difficult to digest

Cows have microbes in their stomachs to facilitate this process
Figure 5.9
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.
(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
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)
Fatty acids
Vary in the length and number and locations of double bonds they contain
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

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
Phospholipids Phospholipids
Have only two fatty acids
Have a phosphate group instead of a third fatty acid
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
The structure of phospholipids

Results in a bilayer arrangement found in cell membranes
WATER Hydrophilic head
WATER Hydrophobic tail
Figure 5.14
Steroids Steroids
Are lipids characterized by a carbon skeleton consisting of four fused rings
One steroid, cholesterol

Is found in cell membranes
Is a precursor for some hormones

H3C CH3 CH3
CH3
CH3
Figure 5.15
HO
Concept 5.4: Proteins have many structures, resulting in a wide range of functions
Proteins Have many roles inside the cell
An overview of protein functions
Table 5.1
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

3 Substrate is converted to products.
Polypeptides Polypeptides
Are polymers of amino acids
A protein
Consists of one or more polypeptides
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
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
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)
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)
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
Protein Conformation and Function A proteins specific conformation

Determines how it functions
Two models of protein conformation
Groove
(a) A ribbon model
Groove
Figure 5.19
(b) A space-filling model
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
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
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
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

The four levels of protein structure
+H N 3
Amino end Amino acid subunits
helix
Sickle-Cell Disease: A Simple Change in Primary Structure Sickle-cell disease

Results from a single amino acid substitution in the protein hemoglobin
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
What Determines Protein Conformation? Protein conformation

Depends on the physical and chemical conditions of the proteins environment
Denaturation
Is when a protein unravels and loses its native conformation
Denaturation
Normal protein
Renaturation
Denatured protein
Figure 5.22
The Protein-Folding Problem Most proteins

Probably go through several intermediate states on their way to a stable conformation
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.
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
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
The Roles of Nucleic Acids There are two types of nucleic acids
Deoxyribonucleic acid (DNA)
Ribonucleic acid (RNA)
DNA
Stores information for the synthesis of specific proteins
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
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
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
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
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
The sequence of bases along a nucleotide polymer

Is unique for each gene
The DNA Double Helix Cellular DNA molecules

Have two polynucleotides that spiral around an imaginary axis Form a double helix
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
The nitrogenous bases in DNA

Form hydrogen bonds in a complementary fashion (A with T only, and C with G only)
DNA and Proteins as Tape Measures of Evolution Molecular comparisons

Help biologists sort out the evolutionary connections among species
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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Chapter 5

The Structure and Function of Macromolecules

Lectures by Chris Romero

Overview: The Molecules of Life

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Dehydration removes a water molecule, forming a new bond

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

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Polymers can disassemble by

Hydrolysis adds a water molecule, breaking a bond

Figure 5.2B (b) Hydrolysis of a polymer

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

The Diversity of Polymers Each class of polymer

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Concept 5.2: Carbohydrates serve as fuel and building material Carbohydrates

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Can be used for fuel

Can be combined into polymers

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Hexose sugars (C6H12O6)

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Can form rings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Are joined by a glycosidic linkage

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Serve many roles in organisms

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Storage Polysaccharides Starch

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Is the major storage form of glucose in plants

Figure 5.6 (a) Starch: a plant polysaccharide

Is the major storage form of glucose in animals

Glycogen Figure 5.6 (b) Glycogen: an animal polysaccharide

Structural Polysaccharides Cellulose

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Has different glycosidic linkages than starch

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

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

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

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

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

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

A cellulose molecule is an unbranched glucose polymer.

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Cellulose is difficult to digest

Chitin, another important structural polysaccharide

Concept 5.3: Lipids are a diverse group of hydrophobic molecules Lipids

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Fatty acid (palmitic acid)

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

(b) Fat molecule (triacylglycerol)

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings

Saturated fatty acids

Figure 5.12 (a) Saturated fat and fatty acid

Unsaturated fatty acids

(b) Unsaturated fat and fatty acid

cis double bond causes bending

Copyright 2005 Pearson Education, Inc. publishing as Benjamin Cummings