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Contents in Brief
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Detailed Contents
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Detailed Contents ix
2.4 What Properties of Water Give It a Unique Role There Are 20 Common Amino Acids 77
in the Environment? 50 Are There Other Ways to Classify Amino Acids? 80
SUMMARY 50 Amino Acids 21 and 22—and More? 81
PROBLEMS 51 Several Amino Acids Occur Only Rarely in Proteins 81
FURTHER READING 52 Amino Acid Derivatives 82
3 Thermodynamics of Biological Systems 53 4.2 What Are the Acid–Base Properties of Amino
Acids? 82
3.1 What Are the Basic Concepts of
Amino Acids Are Weak Polyprotic Acids 82
Thermodynamics? 54
The First Law: The Total Energy of an Isolated System Side Chains of Amino Acids Undergo Characteristic
Is Conserved 54 Ionizations 84
Enthalpy Is a More Useful Function for Biological Isoelectric Points of Amino Acids 85
Systems 55 4.3 What Are the Post-translational Modifications
The Second Law: Systems Tend Toward Disorder and of Amino Acids? 86
Randomness 57 4.4 What Are the Optical and Stereochemical
A DEEPER LOOK: Entropy, Information, and the Properties of Amino Acids? 86
Importance of “Negentropy” 58 Amino Acids Are Chiral Molecules 86
The Third Law: Why Is “Absolute Zero” So Important? 58 Chiral Molecules Are Described by the d,l and R,S
Free Energy Provides a Simple Criterion for Equilibrium 58 Naming Conventions 86
3.2 What Can Thermodynamic Parameters Tell CRITICAL DEVELOPMENTS IN BIOCHEMISTRY:
Us about Biochemical Events? 60 Green Fluorescent Protein—The “Light Fantastic” from
Jellyfish to Gene Expression 87
3.3 What Are the Characteristics of High-Energy
Biomolecules? 61 4.5 What Are the Spectroscopic Properties
ATP Is an Intermediate Energy-Shuttle Molecule 62 of Amino Acids? 87
Group Transfer Potentials Quantify the Reactivity CRITICAL DEVELOPMENTS IN BIOCHEMISTRY:
of Functional Groups 63 Discovery of Optically Active Molecules and
Determination of Absolute Configuration 88
The Hydrolysis of Phosphoric Acid Anhydrides
Is Highly Favourable 64 Phenylalanine, Tyrosine, and Tryptophan Absorb
Ultraviolet Light 88
The Hydrolysis ⌬G°’ of ATP and ADP Is Greater Than
That of AMP 66 Amino Acids Can Be Characterized by Nuclear
Magnetic Resonance 89
Acetyl Phosphate and 1,3-Bisphosphoglycerate
Are Phosphoric-Carboxylic Anhydrides 67 A DEEPER LOOK: The Murchison Meteorite—
Discovery of Extraterrestrial Handedness 90
Enol Phosphates Are Potent Phosphorylating Agents 67
CRITICAL DEVELOPMENTS IN BIOCHEMISTRY:
Guanidino Phosphates Are Energy Reserve
Rules for Description of Chiral Centres in the (R,S)
Compounds 68
System 91
3.4 What Are the Complex Equilibria Involved
4.6 What Is the Fundamental Structural Pattern
in ATP Hydrolysis? 69
in Proteins? 91
The ⌬G°’ of Hydrolysis for ATP Is pH Dependent 69
The Peptide Bond Has Partial Double-Bond
Metal Ions Affect the Free Energy of Hydrolysis of ATP 70 Character 92
Concentration Affects the Free Energy of Hydrolysis The Polypeptide Backbone Is Relatively Polar 92
of ATP 70
Peptides Can Be Classified According to How Many
3.5 Why Are Coupled Processes Important Amino Acids They Contain 94
to Living Things? 71 Proteins Are Composed of One or More Polypeptide
3.6 What Is the Daily Human Requirement for ATP? 71 Chains 94
A DEEPER LOOK: ATP Changes the Keq by a Factor of SUMMARY 95
108 72
PROBLEMS 96
SUMMARY 73
FURTHER READING 97
PROBLEMS 73
FURTHER READING 74 5 Proteins: Their Primary Structure and Biological
Functions 98
4 Amino Acids 75 5.1 What Architectural Arrangements Characterize
4.1 What Are the Structures and Properties Protein Structure? 99
of Amino Acids? 76 Protein Structure Is Described in Terms of Four Levels
Typical Amino Acids Contain a Central Tetrahedral of Organization 99
Carbon Atom 76 Non-covalent Forces Drive Formation of the Higher
Amino Acids Can Join via Peptide Bonds 76 Orders of Protein Structure 101
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x Detailed Contents
Proteins Fall into Three Basic Classes According A Mutant Protein Is a Protein with a Slightly Different
to Shape and Solubility 101 Amino Acid Sequence 128
A Protein’s Conformation Can Be Described as Its A DEEPER LOOK: Bovine Spongiform Encephalopathy
Overall Three-Dimensional Structure 102 (BSE) and Its Effect on the Canadian Economy 130
5.2 How Are Proteins Isolated and Purified 5.7 Can Polypeptides Be Synthesized in the
from Cells? 102 Laboratory? 130
Dialysis and Ultrafiltration 103 Solid-Phase Methods Are Very Useful in Peptide
A Number of Protein Separation Methods Exploit Synthesis 130
Differences in Size and Charge 103 5.8 Do Proteins Have Chemical Groups Other Than
A Typical Protein Purification Scheme Uses a Series Amino Acids? 132
of Separation Methods 104 5.9 What Are the Many Biological Functions of
A DEEPER LOOK: Estimation of Protein Concentrations Proteins? 133
in Solutions of Biological Origin 104 SUMMARY 135
5.3 How Are Amino Acid Mixtures Separated? 105 PROBLEMS 136
Amino Acids Can Be Separated by FURTHER READING 138
Chromatography 105
Summary of the Types of Chromatographic 6 Proteins: Secondary, Tertiary, and Quaternary
Techniques 105 Structure 140
5.4 How Is the Amino Acid Analysis of Proteins 6.1 What Non-covalent Interactions Stabilize
Performed? 111 Protein Structure? 141
Acid Hydrolysis Liberates the Amino Acids of a Hydrogen Bonds Are Formed Whenever Possible 142
Protein 111
Hydrophobic Interactions Drive Protein Folding 142
Chromatographic Methods Are Used to Separate
Ionic Interactions Usually Occur on the Protein
the Amino Acids 111
Surface 142
The Amino Acid Compositions of Different Proteins
Van der Waals Interactions Are Ubiquitous 142
Are Different 111
6.2 What Role Does the Amino Acid Sequence Play
5.5 How Is the Primary Structure of a Protein
in Protein Structure? 143
Determined? 111
The Sequence of Amino Acids in a Protein Is 6.3 What Are the Elements of Secondary Structure
Distinctive 111 in Proteins, and How Are They Formed? 143
Sanger Was the First to Determine the Sequence All Protein Structure Is Based on the Amide Plane 143
of a Protein 112 The Alpha-Helix Is a Key Secondary Structure 145
Both Chemical and Enzymatic Methodologies A DEEPER LOOK: Knowing What the Right Hand and
Are Used in Protein Sequencing 112 Left Hand Are Doing 146
Step 1. Separation of Polypeptide Chains 112 The b-Pleated Sheet Is a Core Structure in
A DEEPER LOOK: The Virtually Limitless Number of Proteins 149
Different Amino Acid Sequences 113 CRITICAL DEVELOPMENTS IN BIOCHEMISTRY: In
Step 2. Cleavage of Disulfide Bridges 113 Bed with a Cold, Pauling Stumbles onto the a-Helix
and a Nobel Prize 150
Step 3. N- and C-Terminal Analysis 113
Helix–Sheet Composites in Spider Silk 151
Steps 4 and 5. Fragmentation of the Polypeptide
Chain 115 b-Turns Allow the Protein Strand to Change
Direction 152
Step 6. Reconstruction of the Overall Amino Acid
Sequence 118 6.4 How Do Polypeptides Fold into Three-Dimensional
Protein Structures? 152
The Amino Acid Sequence of a Protein Can Be
Determined by Mass Spectrometry 118 Fibrous Proteins Usually Play a Structural Role 153
Sequence Databases Contain the Amino Acid A DEEPER LOOK: The Coiled-Coil Motif in
Sequences of Millions of Different Proteins 122 Proteins 155
5.6 What Is the Nature of Amino Acid Sequences? 122 Globular Proteins Mediate Cellular Function 159
Homologous Proteins from Different Organisms Helices and Sheets Make Up the Core of Most
Have Homologous Amino Acid Sequences 122 Globular Proteins 159
Computer Programs Can Align Sequences and Waters on the Protein Surface Stabilize the
Discover Homology between Proteins 123 Structure 160
Related Proteins Share a Common Evolutionary Packing Considerations 160
Origin 125 HUMAN BIOCHEMISTRY: Collagen-Related
Apparently Different Proteins May Share a Common Diseases 162
Ancestry 128 Protein Domains Are Nature’s Modular Strategy
for Protein Design 162
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Detailed Contents xi
Classification Schemes for the Protein Universe Are Haworth Projections Are a Convenient Device
Based on Domains 164 for Drawing Sugars 195
Denaturation Leads to Loss of Protein Structure and Monosaccharides Can Be Converted to Several
Function 166 Derivative Forms 196
Anfinsen’s Classic Experiment Proved That Sequence A DEEPER LOOK: Honey: An Ancestral Carbohydrate
Determines Structure 168 Treat 199
Is There a Single Mechanism for Protein Folding? 169 7.3 What Is the Structure and Chemistry
What Is the Thermodynamic Driving Force for Folding of Oligosaccharides? 200
of Globular Proteins? 170 Disaccharides Are the Simplest Oligosaccharides 200
Marginal Stability of the Tertiary Structure Makes A DEEPER LOOK: Trehalose: A Natural Protectant for
Proteins Flexible 171 Bugs 202
Motion in Globular Proteins 172 A Variety of Higher Oligosaccharides Occur in
The Folding Tendencies and Patterns of Globular Nature 202
Proteins 172 7.4 What Is the Structure and Chemistry of
Most Globular Proteins Belong to One of Four Polysaccharides? 203
Structural Classes 174 Nomenclature for Polysaccharides Is Based
Molecular Chaperones Are Proteins That Help Other on Their Composition and Structure 203
Proteins to Fold 176 Polysaccharides Serve Energy Storage, Structure,
Some Proteins Are Intrinsically Unstructured 176 and Protection Functions 203
HUMAN BIOCHEMISTRY: A1-Antitrypsin: A Tale of Polysaccharides Provide Stores of Energy 204
Molecular Mousetraps and a Folding Disease 178 Polysaccharides Provide Physical Structure
HUMAN BIOCHEMISTRY: Diseases of Protein and Strength to Organisms 205
Folding 179 A DEEPER LOOK: A Complex Polysaccharide in Red
HUMAN BIOCHEMISTRY: Structural Genomics 179 Wine: The Strange Story of Rhamnogalacturonan II 208
6.5 How Do Protein Subunits Interact at the A DEEPER LOOK: Billiard Balls, Exploding Teeth, and
Quaternary Level of Protein Structure? 179 Dynamite: The Colourful History of Cellulose 210
There Is Symmetry in Quaternary Structures 181 Polysaccharides Provide Strength and Rigidity to
Quaternary Association Is Driven by Weak Forces 183 Bacterial Cell Walls 210
A DEEPER LOOK: Immunoglobulins: All the Features Peptidoglycan Is the Polysaccharide of Bacterial
of Protein Structure Brought Together 184 Cell Walls 210
Immunoglobulin-Based Techniques 184 Animals Display a Variety of Cell Surface
Polysaccharides 212
Open Quaternary Structures Can Polymerize 184
There Are Structural and Functional Advantages to 7.5 What Are Glycoproteins, and How Do They
Quaternary Association 184 Function in Cells? 213
HUMAN BIOCHEMISTRY: Faster-Acting Insulin: Polar Fish Depend on Antifreeze Glycoproteins 215
Genetic Engineering Solves a Quaternary Structure A DEEPER LOOK: Drug Research Finds a Sweet Spot 216
Problem 185 N-Linked Oligosaccharides Can Affect the Physical
CRITICAL DEVELOPMENTS IN BIOCHEMISTRY: Properties and Functions of a Protein 216
Banting and Best: The Great Canadian Discovery 185 Oligosaccharide Cleavage Can Serve as a Timing
SUMMARY 186 Device for Protein Degradation 216
PROBLEMS 187 A DEEPER LOOK: N-Linked Oligosaccharides Help
Proteins Fold 218
FURTHER READING 187
7.6 How Do Proteoglycans Modulate Processes in
7 Carbohydrates and the Glycoconjugates of Cell Cells and Organisms? 218
Surfaces 189 Functions of Proteoglycans Involve Binding to Other
Proteins 218
BIOCHEMISTRY: A CANADIAN CONTEXT: The
Proteoglycans May Modulate Cell Growth
Synthesis of Sucrose 190
Processes 220
7.1 What Are Carbohydrates, and How Are They
Proteoglycans Make Cartilage Flexible and
Named? 190
Resilient 221
7.2 What Is the Structure and Chemistry
7.7 Do Carbohydrates Provide a Structural Code? 222
of Monosaccharides? 191
Selectins, Rolling Leukocytes, and the Inflammatory
Monosaccharides Are Classified as Aldoses and
Response 222
Ketoses 191
Galectins: Mediators of Inflammation, Immunity, and
Stereochemistry Is a Prominent Feature of
Cancer 223
Monosaccharides 192
C-Reactive Protein: A Lectin That Limits Inflammation
Monosaccharides Exist in Cyclic and Anomeric Forms 193
Damage 224
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xii Detailed Contents
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Detailed Contents xiii
Eicosanoids Are Local Hormones 278 Lipids Form Ordered Structures Spontaneously in
Prostaglandins Are Formed from Arachidonate Water 302
by Oxidation and Cyclization 278 The Fluid Mosaic Model Describes Membrane
A Variety of Stimuli Trigger Arachidonate Release Dynamics 304
and Eicosanoid Synthesis 278 10.2 What Are the Structure and Chemistry
A DEEPER LOOK: The Discovery of Prostaglandins 278 of Membrane Proteins? 306
A DEEPER LOOK: The Molecular Basis for the Action Peripheral Membrane Proteins Associate Loosely
of Non-steroidal Anti-inflammatory Drugs 280 with the Membrane 306
“Take Two Aspirin and…” Inhibit Your Prostaglandin Integral Membrane Proteins Are Firmly Anchored
Synthesis 281 in the Membrane 307
9.4 How Is Cholesterol Synthesized? 282 Lipid-Anchored Membrane Proteins Are Switching
Mevalonate Is Synthesized from Acetyl-CoA via Devices 314
HMG-CoA Synthase 282 A DEEPER LOOK: Exterminator Proteins—Biological
A Thiolase Brainteaser Asks Why Thiolase Cannot Be Pest Control at the Membrane 315
Used in Fatty Acid Synthesis 283 HUMAN BIOCHEMISTRY: Prenylation Reactions as
Squalene Is Synthesized from Mevalonate 283 Possible Chemotherapy Targets 317
CRITICAL DEVELOPMENTS IN BIOCHEMISTRY: 10.3 How Are Biological Membranes Organized? 318
The Long Search for the Route of Cholesterol Membranes Are Asymmetric and Heterogeneous
Biosynthesis 285 Structures 318
HUMAN BIOCHEMISTRY: Statins Lower Serum 10.4 What Are the Dynamic Processes That Modulate
Cholesterol Levels 286 Membrane Function? 319
Conversion of Lanosterol to Cholesterol Requires Lipids and Proteins Undergo a Variety of Movements
Twenty Additional Steps 286 in Membranes 319
9.5 How Are Lipids Transported throughout the Body? 288 Membrane Lipids Can Be Ordered to Different
Lipoprotein Complexes Transport Triacylglycerols Extents 320
and Cholesterol Esters 288 10.5 How Does Transport Occur across Biological
Lipoproteins in Circulation Are Progressively Degraded Membranes? 327
by Lipoprotein Lipase 289 10.6 What Is Passive Diffusion? 328
The Structure of the LDL Receptor Involves Five Charged Species May Cross Membranes by Passive
Domains 289 Diffusion 329
The LDL Receptor -Propeller Displaces LDL Particles 10.7 How Does Facilitated Diffusion Occur? 329
in Endosomes 291 Membrane Channel Proteins Facilitate
Defects in Lipoprotein Metabolism Can Lead to Diffusion 329
Elevated Serum Cholesterol 291 The Bacillus cereus NaK Channel Uses a Variation on
9.6 How Are Bile Acids Biosynthesized? 292 the K+ Selectivity Filter 333
HUMAN BIOCHEMISTRY: Steroid 5a-Reductase: CorA Is a Pentameric Mg2+ Channel 333
A Factor in Male Baldness, Prostatic Hyperplasia, and Chloride, Water, Glycerol, and Ammonia Flow
Prostate Cancer 293 through Single-Subunit Pores 334
9.7 How Are Steroid Hormones Synthesized and 10.8 How Does Energy Input Drive Active Transport
Utilized? 293 Processes? 335
Pregnenolone and Progesterone Are the Precursors All Active Transport Systems Are Energy-Coupling
of All Other Steroid Hormones 293 Devices 335
Steroid Hormones Modulate Transcription in the Many Active Transport Processes Are Driven by
Nucleus 294 ATP 335
Cortisol and Other Corticosteroids Regulate a Variety A DEEPER LOOK: Cardiac Glycosides: Potent Drugs
of Body Processes 295 from Ancient Times 340
Anabolic Steroids Have Been Used Illegally to ABC Transporters Use ATP to Drive Import and Export
Enhance Athletic Performance 295 Functions and Provide Multidrug Resistance 340
SUMMARY 295 10.9 How Are Certain Transport Processes Driven
PROBLEMS 296 by Light Energy? 341
FURTHER READING 297 Bacteriorhodopsin Uses Light Energy to Drive Proton
Transport 343
10 Membranes and Membrane Transport 299 10.10 How Is Secondary Active Transport Driven
10.1 What Are the Chemical and Physical Properties by Ion Gradients? 343
of Membranes 300 Na+ and H+ Drive Secondary Active Transport 343
The Composition of Membranes Suits Their AcrB Is a Secondary Active Transport System 343
Functions 301
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xiv Detailed Contents
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Detailed Contents xv
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xvi Detailed Contents
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deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Detailed Contents xvii
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xviii Detailed Contents
Amphibolic Intermediates Play Dual Roles 546 Reaction 7: Phosphoglycerate Kinase Is the Break-
Corresponding Pathways of Catabolism and Even Reaction 575
Anabolism Differ in Important Ways 546 Reaction 8: Phosphoglycerate Mutase Catalyzes
ATP Serves in a Cellular Energy Cycle 546 a Phosphoryl Transfer 576
NAD Collects Electrons Released in Catabolism 547 Reaction 9: Dehydration by Enolase Creates PEP 577
NADPH Provides the Reducing Power for Anabolic Reaction 10: Pyruvate Kinase Yields More ATP 577
Processes 548 17.5 What Are the Metabolic Fates of NADH and
Coenzymes and Vitamins Provide Unique Chemistry Pyruvate Produced in Glycolysis? 580
and Essential Nutrients to Pathways 549 Anaerobic Metabolism of Pyruvate Leads
16.4 What Experiments Can Be Used to Elucidate to Lactate or Ethanol 580
Metabolic Pathways? 550 Lactate Accumulates under Anaerobic Conditions
Mutations Create Specific Metabolic Blocks 551 in Animal Tissues 581
Isotopic Tracers Can Be Used as Metabolic Probes 551 17.6 How Do Cells Regulate Glycolysis? 581
NMR Spectroscopy Is a Non-invasive Metabolic 17.7 Are Substrates Other Than Glucose Used
Probe 552 in Glycolysis? 581
Metabolic Pathways Are Compartmentalized within HUMAN BIOCHEMISTRY: Tumour Diagnosis Using
Cells 553 Positron Emission Tomography (PET) 582
16.5 What Can the Metabolome Tell Us about Mannose Enters Glycolysis in Two Steps 583
a Biological System? 555 Galactose Enters Glycolysis via the Leloir Pathway 583
16.6 What Food Substances Form the Basis of Human An Enzyme Deficiency Causes Lactose Intolerance 585
Nutrition? 557 Glycerol Can Also Enter Glycolysis 585
Humans Require Protein 557 HUMAN BIOCHEMISTRY: Lactose—From Mother’s
Carbohydrates Provide Metabolic Energy 557 Milk to Yogurt—and Lactose Intolerance 585
A DEEPER LOOK: A Popular Fad Diet—Low 17.8 How Do Cells Respond to Hypoxic Stress? 586
Carbohydrates, High Protein, High Fat 557 SUMMARY 587
Lipids Are Essential, But in Moderation 558
PROBLEMS 588
Fibre May Be Soluble or Insoluble 558
FURTHER READING 589
SUMMARY 558
PROBLEMS 559 18 The Tricarboxylic Acid Cycle 591
FURTHER READING 559 18.1 What Is the Chemical Logic of the TCA
Cycle? 593
17 Glycolysis 561 The TCA Cycle Provides a Chemically Feasible Way of
17.1 What Are the Essential Features of Glycolysis? 562 Cleaving a 2-Carbon Compound 593
17.2 Why Are Coupled Reactions Important in 18.2 How Is Pyruvate Oxidatively Decarboxylated
Glycolysis? 563 to Acetyl-CoA? 595
17.3 What Are the Chemical Principles and Features A DEEPER LOOK: The Coenzymes of the Pyruvate
of the First Phase of Glycolysis? 564 Dehydrogenase Complex 597
Reaction 1: Glucose Is Phosphorylated by Hexokinase 18.3 How Are 2 CO2 Molecules Produced from
or Glucokinase—The First Priming Reaction 565 Acetyl-CoA? 600
Reaction 2: Phosphoglucoisomerase Catalyzes the The Citrate Synthase Reaction Initiates the TCA
Isomerization of Glucose-6-Phosphate 568 Cycle 600
Reaction 3: ATP Drives a Second Phosphorylation Isocitrate Dehydrogenase Catalyzes the First Oxidative
by Phosphofructokinase—The Second Priming Decarboxylation in the Cycle 602
Reaction 569 a-Ketoglutarate Dehydrogenase Catalyzes the Second
A DEEPER LOOK: Phosphoglucoisomerase: Oxidative Decarboxylation of the TCA Cycle 603
A Moonlighting Protein 570 18.4 How Is Oxaloacetate Regenerated to Complete
Reaction 4: Cleavage by Fructose Bisphosphate the TCA Cycle? 604
Aldolase Creates Two, Three-Carbon Succinyl-CoA Synthetase Catalyzes Substrate Level
Intermediates 571 Phosphorylation 604
Reaction 5: Triose Phosphate Isomerase Completes The First 5 Steps of the TCA Cycle Produce NADH,
the First Phase of Glycolysis 572 CO2, GTP (ATP), and Succinate 605
17.4 What Are the Chemical Principles and Features Succinate Dehydrogenase Is FAD Dependent 605
of the Second Phase of Glycolysis? 573 Fumarase Catalyzes the Trans-Hydration of Fumarate
Reaction 6: Glyceraldehyde-3-Phosphate to Form l-Malate 606
Dehydrogenase Creates a High-Energy Malate Dehydrogenase Completes the Cycle by
Intermediate 573 Oxidizing Malate to Oxaloacetate 606
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Detailed Contents xix
18.5 What Are the Energetic Consequences HUMAN BIOCHEMISTRY: Solving a Medical Mystery
of the TCA Cycle? 607 Revolutionized Our Treatment of Parkinson’s
The Carbon Atoms of Acetyl-CoA Have Different Fates Disease 631
in the TCA Cycle 607 Complex II Oxidizes Succinate and Reduces
A DEEPER LOOK: Steric Preferences in NAD- Coenzyme Q 631
Dependent Dehydrogenases 608 Complex III Mediates Electron Transport from
18.6 Can the TCA Cycle Provide Intermediates Coenzyme Q to Cytochrome c 633
for Biosynthesis? 610 Complex IV Transfers Electrons from
HUMAN BIOCHEMISTRY: Mitochondrial Diseases Cytochrome c to Reduce Oxygen on the Matrix
Are Rare 611 Side 635
18.7 What Are the Anaplerotic, or “Filling-Up,” Proton Transport across Cytochrome c Oxidase
Reactions? 611 Is Coupled to Oxygen Reduction 637
A DEEPER LOOK: Fool’s Gold and the Reductive Citric The Four Electron-Transport Complexes Are
Acid Cycle—The First Metabolic Pathway? 612 Independent 638
Electron Transfer Energy Stored in a Proton Gradient:
18.8 How Is the TCA Cycle Regulated? 613
The Mitchell Hypothesis 639
Pyruvate Dehydrogenase Is Regulated by
Phosphorylation/Dephosphorylation 613 19.4 What Are the Thermodynamic Implications
of Chemiosmotic Coupling? 640
Isocitrate Dehydrogenase Is Strongly Regulated 615
19.5 How Does a Proton Gradient Drive
18.9 Can Any Organisms Use Acetate as Their Sole the Synthesis of ATP? 641
Carbon Source? 615
ATP Synthase Is Composed of F1 and F0 641
The Glyoxylate Cycle Operates in Specialized
Organelles 616 The Catalytic Sites of ATP Synthase Adopt Three
Different Conformations 643
Isocitrate Lyase Short-Circuits the TCA Cycle by
Producing Glyoxylate and Succinate 616 Boyer’s 18O Exchange Experiment Identified
the Energy-Requiring Step 643
The Glyoxylate Cycle Helps Plants Grow in
the Dark 617 Boyer’s Binding Change Mechanism Describes
the Events of Rotational Catalysis 644
Glyoxysomes Must Borrow 3 Reactions from
Mitochondria 617 Proton Flow through F0 Drives Rotation of the Motor
and Synthesis of ATP 644
SUMMARY 618
Racker and Stoeckenius Confirmed the Mitchell Model
PROBLEMS 619 in a Reconstitution Experiment 646
FURTHER READING 620 Inhibitors of Oxidative Phosphorylation Reveal Insights
about the Mechanism 646
19 Electron Transport and Oxidative Uncouplers Disrupt the Coupling of Electron Transport
Phosphorylation 621 and ATP Synthase 647
19.1 Where in the Cell Do Electron Transport ATP–ADP Translocase Mediates the Movement
and Oxidative Phosphorylation Occur? 622 of ATP and ADP across the Mitochondrial
Mitochondrial Functions Are Localized in Specific Membrane 648
Compartments 622 HUMAN BIOCHEMISTRY: Endogenous
The Mitochondrial Matrix Contains the Enzymes of the Uncouplers Enable Organisms to Generate
TCA Cycle 623 Heat 649
19.2 What Are Reduction Potentials, and How Are 19.6 What Is the P/O Ratio for Mitochondrial Oxidative
They Used to Account for Free Energy Changes Phosphorylation? 649
in Redox Reactions? 623 19.7 How Are the Electrons of Cytosolic NADH Fed
Standard Reduction Potentials Are Measured into Electron Transport? 650
in Reaction Half-Cells 624 The Glycerophosphate Shuttle Ensures Efficient
e0’ Values Can Be Used to Predict the Direction Use of Cytosolic NADH 651
of Redox Reactions 625 The Malate–Aspartate Shuttle Is Reversible 651
e0’ Values Can Be Used to Analyze Energy Changes The Net Yield of ATP from Glucose Oxidation
in Redox Reactions 626 Depends on the Shuttle Used 652
The Reduction Potential Depends on 3.5 Billion Years of Evolution Have Resulted
Concentration 626 in a Very Efficient System 653
19.3 How Is the Electron-Transport Chain 19.8 How Do Mitochondria Mediate Apoptosis? 653
Organized? 627 Cytochrome c Triggers Apoptosome Assembly 654
The Electron-Transport Chain Can Be Isolated in
SUMMARY 655
Four Complexes 628
PROBLEMS 656
Complex I Oxidizes NADH and Reduces
Coenzyme Q 629 FURTHER READING 658
NEL
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xx Detailed Contents
20 Photosynthesis 659
Cyclic Photophosphorylation Generates ATP but Not
NADPH or O2 679
20.1 What Are the General Properties of
20.7 How Is Carbon Dioxide Used to Make Organic
Photosynthesis? 660
Molecules? 680
Photosynthesis Occurs in Membranes 660
Ribulose-1,5-Bisphosphate Is the CO2 Acceptor in CO2
Photosynthesis Consists of Both Light Reactions Fixation 680
and Dark Reactions 662
2-Carboxy-3-Keto-Arabinitol Is an Intermediate in the
Water Is the Ultimate e Donor for Photosynthetic Ribulose-1,5-Bisphosphate Carboxylase Reaction 681
NADP Reduction 663
Ribulose-1,5-Bisphosphate Carboxylase Exists in
20.2 How Is Solar Energy Captured by Chlorophyll? 663 Inactive and Active Forms 681
Chlorophylls and Accessory Light-Harvesting Pigments CO2 Fixation into Carbohydrate Proceeds
Absorb Light of Different Wavelengths 664 via the Calvin–Benson Cycle 682
The Light Energy Absorbed by Photosynthetic The Enzymes of the Calvin Cycle Serve 3 Metabolic
Pigments Has Several Possible Fates 665 Purposes 682
The Transduction of Light Energy into Chemical Energy The Calvin Cycle Reactions Can Account for Net
Involves Oxidation–Reduction 666 Hexose Synthesis 683
Photosynthetic Units Consist of Many Chlorophyll The Carbon Dioxide Fixation Pathway Is Indirectly
Molecules but Only a Single Reaction Centre 667 Activated by Light 683
20.3 What Kinds of Photosystems Are Used to Capture Light Induces Movement of Mg2 Ions from the
Light Energy? 667 Thylakoid Vesicles into the Stroma 686
Chlorophyll Exists in Plant Membranes in Association Protein–Protein Interactions Mediated by an
with Proteins 668 Intrinsically Unstructured Protein Also Regulate
PSI and PSII Participate in the Overall Process of Calvin–Benson Cycle Activity 686
Photosynthesis 668 20.8 How Does Photorespiration Limit CO2
The Pathway of Photosynthetic Electron Transfer Fixation? 686
Is Called the Z Scheme 668 Tropical Grasses Use the Hatch–Slack Pathway to
Oxygen Evolution Requires the Accumulation of 4 Capture Carbon Dioxide for CO2 Fixation 686
Oxidizing Equivalents in PSII 670 Cacti and Other Desert Plants Capture CO2 at
Electrons Are Taken from H2O to Replace Electrons Night 689
Lost from P680 670 SUMMARY 689
Electrons from PSII Are Transferred to PSI via the PROBLEMS 690
Cytochrome b6f Complex 670
FURTHER READING 691
Plastocyanin Transfers Electrons from the Cytochrome
b6f Complex to PSI 671
21 Gluconeogenesis, Glycogen Metabolism, and
20.4 What Is the Molecular Architecture of the Pentose Phosphate Pathway 693
Photosynthetic Reaction Centres? 671
21.1 What Is Gluconeogenesis, and How Does It
The R. viridis Photosynthetic Reaction Centre Is an
Operate? 694
Integral Membrane Protein 672
BIOCHEMISTRY: A CANADIAN CONTEXT:
Photosynthetic Electron Transfer by the R. viridis
Reaction Centre Leads to ATP Synthesis 672 Determining the Kinetic Mechanism of
Phosphoenolpyruvate Carboxykinase 694
The Molecular Architecture of PSII Resembles the
R. viridis Reaction Centre Architecture 673 The Substrates for Gluconeogenesis Include Pyruvate,
Lactate, and Amino Acids 695
How Does PSII Generate O2 from H2O? 674
Nearly All Gluconeogenesis Occurs in the Liver and
The Molecular Architecture of PSI Resembles the
Kidneys in Animals 695
R. viridis Reaction Centre and PSII Architecture 675
HUMAN BIOCHEMISTRY: The Chemistry of Glucose
How Do Green Plants Carry Out Photosynthesis? 675
Monitoring Devices 695
20.5 What Is the Quantum Yield of Photosynthesis? 677
Gluconeogenesis Is Not Merely the Reverse of
Calculation of the Photosynthetic Energy Glycolysis 696
Requirements for Hexose Synthesis Depends on
Gluconeogenesis: Something Borrowed, Something
H/hn and ATP/H Ratios 677
New 696
20.6 How Does Light Drive the Synthesis of ATP? 677 Four Reactions Are Unique to Gluconeogenesis 696
The Mechanism of Photophosphorylation Is HUMAN BIOCHEMISTRY: Gluconeogenesis Inhibitors
Chemiosmotic 678 and Other Diabetes Therapy Strategies 701
CF1CF0–ATP Synthase Is the Chloroplast Equivalent of
21.2 How Is Gluconeogenesis Regulated? 701
the Mitochondrial F1F0–ATP Synthase 678
CRITICAL DEVELOPMENTS IN BIOCHEMISTRY:
Photophosphorylation Can Occur in Either a
The Pioneering Studies of Carl and Gerty Cori 702
Non-cyclic or a Cyclic Mode 678
NEL
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Detailed Contents xxi
NEL
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xxii Detailed Contents
Ketone Bodies Are a Significant Source of Fuel and A DEEPER LOOK: Amino Acid Biosynthesis Inhibitors
Energy for Certain Tissues 756 as Herbicides 795
HUMAN BIOCHEMISTRY: Large Amounts of Ketone A DEEPER LOOK: Intramolecular Tunnels Connect
Bodies Are Produced in Diabetes Mellitus 757 Distant Active Sites in Some Enzymes 796
SUMMARY 757 Histidine Biosynthesis and Purine Biosynthesis Are
PROBLEMS 758 Connected by Common Intermediates 796
FURTHER READING 759 23.5 How Does Amino Acid Catabolism Lead into
Pathways of Energy Production? 798
23 Nitrogen Acquisition and Amino Acid The Twenty Common Amino Acids Are Degraded
Metabolism 761 by Twenty Different Pathways That Converge to Just
Seven Metabolic Intermediates 798
23.1 Which Metabolic Pathways Allow Organisms
A DEEPER LOOK: Histidine—A Clue to Understanding
to Live on Inorganic Forms of Nitrogen? 762
Early Evolution? 800
Nitrogen Is Cycled between Organisms
A DEEPER LOOK: The Serine Dehydratase Reaction:
and the Inanimate Environment 762
A b-Elimination 801
Nitrate Assimilation Is the Principal Pathway
HUMAN BIOCHEMISTRY: Hereditary Defects
for Ammonium Biosynthesis 763
in Phe Catabolism Underlie Alkaptonuria and
Nitrate Reductase Contains Cytochrome b557 and Phenylketonuria 804
Molybdenum Cofactor 763
Animals Differ in the Form of Nitrogen That They
Organisms Gain Access to Atmospheric N2 via the Excrete 804
Pathway of Nitrogen Fixation 764
SUMMARY 804
23.2 What Is the Metabolic Fate of Ammonium? 768
PROBLEMS 805
The Major Pathways of Ammonium Assimilation Lead
to Glutamine Synthesis 769 FURTHER READING 806
23.3 What Regulatory Mechanisms Act on Escherichia
coli Glutamine Synthetase? 770
Glutamine Synthetase Is Allosterically Regulated 771 PART IV Nucleic Acids
Glutamine Synthetase Is Regulated by Covalent
Modification 771
Glutamine Synthetase Is Regulated through Gene
24 Nucleotides and Nucleic Acids 808
Expression 773 24.1 What Are the Structure and Chemistry
of Nitrogenous Bases? 809
23.4 How Do Organisms Synthesize Amino Acids? 773
Three Pyrimidines and 2 Purines are Commonly
HUMAN BIOCHEMISTRY: Human Dietary
Found in Cells 810
Requirements for Amino Acids 775
The Properties of Pyrimidines and Purines Can Be
Amino Acids Are Formed from a-Keto Acids by
Traced to Their Electron-Rich Nature 810
Transamination 775
24.2 What Are Nucleosides? 811
A DEEPER LOOK: The Mechanism of the
Aminotransferase (Transamination) Reaction 776 HUMAN BIOCHEMISTRY: Adenosine: A Nucleoside
with Physiological Activity 812
The Pathways of Amino Acid Biosynthesis Can Be
Organized into Families 776 24.3 What Are the Structure and Chemistry
The a-Ketoglutarate Family of Amino Acids Includes of Nucleotides? 813
Glu, Gln, Pro, Arg, and Lys 777 Cyclic Nucleotides Are Cyclic Phosphodiesters 813
The Urea Cycle Acts to Excrete Excess N Through Arg Nucleoside Diphosphates and Triphosphates Are
Breakdown 778 Nucleotides with 2 or 3 Phosphate Groups 813
A DEEPER LOOK: The Urea Cycle as Both an NDPs and NTPs Are Polyprotic Acids 814
Ammonium and a Bicarbonate Disposal Mechanism 782 Nucleoside 5-Triphosphates Are Carriers of Chemical
The Aspartate Family of Amino Acids Includes Asp, Energy 814
Asn, Lys, Met, Thr, and Ile 782 24.4 What Are Nucleic Acids? 815
HUMAN BIOCHEMISTRY: Asparagine and The Base Sequence of a Nucleic Acid Is Its Distinctive
Leukemia 783 Characteristic 815
The Pyruvate Family of Amino Acids Includes Ala, Val, 24.5 What Are the Different Classes of Nucleic
and Leu 785 Acids? 816
The 3-Phosphoglycerate Family of Amino Acids The Fundamental Structure of DNA Is a Double
Includes Ser, Gly, and Cys 788 Helix 817
The Aromatic Amino Acids Are Synthesized from Various Forms of RNA Serve Different Roles in
Chorismate 790 Cells 819
HUMAN BIOCHEMISTRY: Phenylketonuria and A DEEPER LOOK: Do the Properties of DNA Invite
Aspartame 793 Practical Applications? 820
NEL
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Detailed Contents xxiii
A DEEPER LOOK: The RNA World and Early Single-Stranded DNA Can Renature to Form DNA
Evolution 823 Duplexes 849
The Chemical Differences between DNA and RNA The Rate of DNA Renaturation Is an Index of DNA
Have Biological Significance 824 Sequence Complexity 849
24.6 Are Nucleic Acids Susceptible to Hydrolysis? 825 A DEEPER LOOK: The Buoyant Density of DNA 849
RNA Is Susceptible to Hydrolysis by Base, but DNA Is Nucleic Acid Hybridization: Different DNA Strands of
Not 826 Similar Sequence Can Form Hybrid Duplexes 850
The Enzymes That Hydrolyze Nucleic Acids Are 25.4 Can DNA Adopt Structures of Higher
Phosphodiesterases 826 Complexity? 850
Nucleases Differ in Their Specificity for Different Forms Supercoils Are One Kind of Structural Complexity in
of Nucleic Acid 827 DNA 851
Restriction Enzymes Are Nucleases That Cleave 25.5 What Is the Structure of Eukaryotic
Double-Stranded DNA Molecules 827 Chromosomes? 853
Type II Restriction Endonucleases Are Useful Nucleosomes Are the Fundamental Structural Unit in
for Manipulating DNA in the Lab 827 Chromatin 853
Restriction Endonucleases Can Be Used to Map Higher-Order Structural Organization of Chromatin
the Structure of a DNA Fragment 828 Gives Rise to Chromosomes 854
SUMMARY 831 SMC Proteins Establish Chromosome Organization
PROBLEMS 831 and Mediate Chromosome Dynamics 855
FURTHER READING 832 25.6 Can Nucleic Acids Be Synthesized Chemically? 856
HUMAN BIOCHEMISTRY: Telomeres and
25 Structure of Nucleic Acids 833 Tumours 857
25.1 How Do Scientists Determine the Primary Phosphoramidite Chemistry Is Used to Form
Structure of Nucleic Acids? 834 Oligonucleotides from Nucleotides 857
The Nucleotide Sequence of DNA Can Be Determined Genes Can Be Synthesized Chemically 858
from the Electrophoretic Migration of a Defined 25.7 What Are the Secondary and Tertiary Structures
Set of Polynucleotide Fragments 834 of RNA? 858
Sanger’s Chain Termination, or Dideoxy, Method Transfer RNA Adopts Higher-Order Structure through
Uses DNA Replication to Generate a Defined Set of Intrastrand Base Pairing 861
Polynucleotide Fragments 834 Ribosomal RNA Also Adopts Higher-Order Structure
High-Throughput DNA Sequencing by the Light of through Intrastrand Base Pairing 863
Fireflies 836 Aptamers Are Oligonucleotides Specifically Selected
25.2 What Sorts of Secondary Structures Can Double- for Their Ligand-Binding Ability 865
Stranded DNA Molecules Adopt? 837 SUMMARY 867
Conformational Variation in Polynucleotide PROBLEMS 868
Strands 837
FURTHER READING 869
DNA Usually Occurs in the Form of Double-Stranded
Molecules 838
26 Synthesis and Degradation of Nucleotides 871
Watson–Crick Base Pairs Have Virtually Identical
26.1 Can Cells Synthesize Nucleotides? 872
Dimensions 838
The DNA Double Helix Is a Stable Structure 839 26.2 How Do Cells Synthesize Purines? 872
Double-Helical Structures Can Adopt a Number of IMP Is the Immediate Precursor to GMP and
Stable Conformations 839 AMP 872
A-Form DNA Is an Alternative Form of Right-Handed A DEEPER LOOK: Tetrahydrofolate and 1-Carbon
DNA 841 Units 875
Z-DNA Is a Conformational Variation in the Form AMP and GMP Are Synthesized from IMP 876
of a Left-Handed Double Helix 841 HUMAN BIOCHEMISTRY: Folate Analogs as
The Double Helix Is a Very Dynamic Structure 843 Antimicrobial and Anticancer Agents 877
Alternative Hydrogen-Bonding Interactions Give Rise The Purine Biosynthetic Pathway Is Regulated at
to Novel DNA Structures: Cruciforms, Triplexes, and Several Steps 877
Quadruplexes 845 ATP-Dependent Kinases Form Nucleoside
Diphosphates and Triphosphates from the Nucleoside
25.3 Can the Secondary Structure of DNA Be Denatured
Monophosphates 878
and Renatured? 847
Thermal Denaturation of DNA Can Be Observed by 26.3 Can Cells Salvage Purines? 879
Changes in UV Absorbance 847 26.4 How Are Purines Degraded? 880
pH Extremes or Strong H-Bonding Solutes Also The Major Pathways of Purine Catabolism Lead to Uric
Denature DNA Duplexes 847 Acid 880
NEL
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