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Copyright 2018 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. WCN 02-200-203
BIOCHEMISTRY
BIOCHEMISTRY
9TH EDITION
Mary K. Campbell
Mount Holyoke College
Shawn O. Farrell
Colorado State University
Owen M. McDougal
Boise State University
Australia ● Brazil ● Mexico ● Singapore ● United Kingdom ● United States
Biochemistry, Ninth Edition © 2018, 2015 Cengage Learning
Mary Campbell, Shawn O. Farrell, Owen ALL RIGHTS RESERVED. No part of this work covered by the copyright herein
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Printed in the United States of America

Print Number: 01 Print Year: 2016
This book is dedicated to the memory of Mary Campbell, who was
passionately involved in its creation. Her avid interest in writing and
devotion to student engagement led to the publication of the first eight
highly successful editions of this textbook.
—Mary K. Campbell
To the returning adult students in my classes, especially those with

children and a full-time job . . . my applause.
—Shawn O. Farrell
My recognition and appreciation go to those who saw the potential in me

that has taken so many years to develop, and to those students who are on
the path to fulfilling their dreams.
—Owen M. McDougal
About the Authors
Mary K. Campbell
Mary K. Campbell was a professor emeritus of chemistry at Mount Holyoke College,
where she taught for 36 years. Mary received her PhD from Indiana University and
did postdoctoral work in biophysical chemistry at Johns Hopkins University. Her area
of interest included researching the physical chemistry of biomolecules, specifically,
spectroscopic studies of protein–nucleic acid interactions.
Shawn O. Farrell
Shawn O. Farrell grew up in northern California and received a B.S. degree in
biochemistry from the University of California, Davis, where he studied carbohydrate
metabolism. He completed his Ph.D. in biochemistry at Michigan State University, where
he studied fatty acid metabolism. For 18 years, Shawn worked at Colorado State University
teaching undergraduate biochemistry lecture and laboratory courses. Because of his
interest in biochemical education, Shawn has written a number of scientific journal articles
about teaching biochemistry. He is the coauthor (with Lynn E. Taylor) of Experiments in
Biochemistry: A Hands-On Approach. Shawn became interested in biochemistry while in
college because it coincided with his passion for bicycle racing. An active outdoorsman,
Shawn raced competitively for 17 years and now officiates at bicycle races around the
world. He was the technical director of USA Cycling, the national governing body of bicycle
racing in the United States for 11 years before returning to teaching at CSU in Pueblo,
Colorado. He is also an avid fly fisherman, a third-degree black belt in Tae Kwon Do, and a
first-degree black belt in combat hapkido. Shawn has also written articles on fly fishing for
Salmon Trout Steelheader magazine. His other passions are music and foreign languages. He
is fluent in Spanish and French and is currently learning to play the guitar.
On his fiftieth birthday, he had his first downhill skiing lesson and now cannot get
enough of it. Never tired of education, he visited CSU again, this time from the other
side of the podium, and earned his Master of Business Administration in 2008.
Owen M. McDougal
Owen M. McDougal is a professor of chemistry and biochemistry at Boise State University.
He is a native of upstate New York where he earned chemistry degrees at State University of
New York at Morrisville (AS) and Oswego (BS). His love of the outdoors motivated him to
travel west for graduate school and pursue a PhD at the University of Utah in the laboratory
of C. Dale Poulter. His work to elucidate the three-dimensional structures of neuropeptides
by nuclear magnetic resonance spectroscopy involved the application of physical chemistry
to address problems in biological systems. Graduate studies in the heart of the Wasatch
Mountains in Utah led to his lifelong enthusiasm for mountain biking and telemark skiing.
In this capacity, Owen tested his skills at competitive mountain bike racing and pursued
what resulted in a ten-year stint on the National Ski Patrol. Upon completion of his PhD,
Owen sought an academic environment that allowed him to share his passion for science
with students in small classes. He taught general, organic, and biological chemistry at
Southern Oregon University, which allowed him to hone his instructional skills. Looking
to advance his love for writing, Owen shifted to a faculty position in the research intensive
environment at Boise State University, where he investigates the bioactivity of marine and
terrestrial natural products, including studies of food chemistry, nutraceutical products,
and specialty chemicals. Owen lives in Boise, Idaho, with wife Lynette, daughters McKenzie
and Riley, dog Tater, cat Melody, tortoise Touché, and rabbit Bixby.
vi
Brief Contents
1 Biochemistry and the Organization of Cells 1
2 Water: The Solvent for Biochemical Reactions 33
3 Amino Acids and Peptides 60
4 The Three-Dimensional Structure of Proteins 78
5 Protein Purification and Characterization Techniques 114
6 The Behavior of Proteins: Enzymes 141
7 The Behavior of Proteins: Enzymes, Mechanisms, and Control 168
8 Lipids and Proteins Are Associated in Biological Membranes 201
9 Nucleic Acids: How Structure Conveys Information 239
10 Biosynthesis of Nucleic Acids: Replication 270
11 Transcription of the Genetic Code: The Biosynthesis of RNA 300
12 Protein Synthesis: Translation of the Genetic Message 347
13 Nucleic Acid Biotechnology Techniques 380
14 Viruses, Cancer, and Immunology 422
15 The Importance of Energy Changes and Electron Transfer in Metabolism 467
16 Carbohydrates 490
17 Glycolysis 520
18 Storage Mechanisms and Control in Carbohydrate Metabolism 550
19 The Citric Acid Cycle 578
20 Electron Transport and Oxidative Phosphorylation 609
21 Lipid Metabolism 636
22 Photosynthesis 675
23 The Metabolism of Nitrogen 701
24 Integration of Metabolism: Cellular Signaling 732
vii
Contents
1 Biochemistry and the 3-3 Amino Acids Can Act as Both Acids
and Bases 66
Organization of Cells 1 3-4 The Peptide Bond 70
1-1 Basic Themes 1 3-5 Small Peptides with Physiological Activity 72
1-2 Chemical Foundations of Biochemistry 2 3A BIOCHEMICAL CONNECTIONS PHYSIOLOGY
1-3 The Beginnings of Biology 6 Peptide Hormones—Small Molecules with Big Effects 73
1-4 The Biggest Biological Distinction— Summary 74
Prokaryotes and Eukaryotes 16 Review exercises 75
1-5 How We Classify Eukaryotes Further Reading 77
and Prokaryotes 21
1A BIOCHEMICAL CONNECTIONS BIOTECHNOLOGY
Extremophiles: The Toast of the Industry 23 4 The Three-Dimensional
1-6 Biochemical Energetics 25 Structure of Proteins 78
1B BIOCHEMICAL CONNECTIONS THERMODYNAMICS
Predicting Reactions 28
4-1 Protein Structure and Function 78
4-2 Primary Structure of Proteins 79
Summary 29
4-3 Secondary Structure of Proteins 79
Review Exercises 30
4-4 Tertiary Structure of Proteins 87
Further Reading 32
4-5 Quaternary Structure of Proteins 93
4A BIOCHEMICAL CONNECTIONS MEDICINE
2 Water: The Solvent for Sickle Cell Anemia 98
Biochemical Reactions 33 4-6 Protein-Folding Dynamics 99
2-1 Water and Polarity 33 4B BIOCHEMICAL CONNECTIONS MEDICINE
2-2 Hydrogen Bonds 38 Protein-Folding Diseases 104
2A BIOCHEMICAL CONNECTIONS CHEMISTRY HOT TOPIC Aging—Looking for the Biochemical Fountain
How Basic Chemistry Affects Life: The Importance of the of Youth 106
Hydrogen Bond 41 Summary 110
2-3 Acids, Bases, and pH 41 Review Exercises 110
2-4 Titration Curves 45 Further Reading 112
2-5 Buffers 48
2B BIOCHEMICAL CONNECTIONS BUFFER CHEMISTRY
Buffer Selection 52 5 Protein Purification and
2C BIOCHEMICAL CONNECTIONS CHEMISTRY OF BLOOD Characterization Techniques 114
Some Physiological Consequences of Blood Buffering 54
5-1 Extracting Pure Proteins from Cells 114
2D BIOCHEMICAL CONNECTIONS ACIDS AND SPORTS 5-2 Column Chromatography 117
Lactic Acid—Not Always the Bad Guy 55
5-3 Electrophoresis 123
Summary 56
5-4 Determining the Primary Structure of a Protein 125
Review Exercises 57
5-5 Protein Detection Techniques 131
Further Reading 59
5A BIOCHEMICAL CONNECTIONS
INSTRUMENTATION
3 Amino Acids and Peptides 60 The Power of Mass Spectrometry 131
3-1 Amino Acids Are Three-Dimensional 60 5-6 Proteomics 136
3-2 Structures and Properties of Amino Acids 61
ix
x Contents
Summary 137 Summary 198

Review Exercises 138 Review Exercises 198
Further Reading 140 Further Reading 200
6 The Behavior of Proteins: 8 Lipids and Proteins Are Associated

Enzymes 141 in Biological Membranes 201
6-1 Enzyme Kinetics vs. Thermodynamics 141 8-1 The Definition of a Lipid 201
6A BIOCHEMICAL CONNECTIONS HEALTH SCIENCES 8-2 The Chemical Natures of the Lipid Types 201
Enzymes as Markers for Disease 144 8-3 Biological Membranes 208
6-2 Rate of Enzyme-Catalyzed Reactions 144 8A BIOCHEMICAL CONNECTIONS NUTRITION
6-3 Enzyme–Substrate Binding 146 Butter versus Margarine–Which Is Healthier? 211
6-4 The Michaelis–Menten Approach to Enzyme 8B BIOCHEMICAL CONNECTIONS BIOTECHNOLOGY
Kinetics 148 Membranes in Drug Delivery 212
6B BIOCHEMICAL CONNECTIONS NEUROSCIENCE 8-4 Membrane Proteins 213
Enzyme Lets You Enjoy Champagne 155 8-5 The Functions of Membranes 216
6C BIOCHEMICAL CONNECTIONS PHYSICAL ORGANIC 8C BIOCHEMICAL CONNECTIONS PHYSIOLOGY
CHEMISTRY Lipid Droplets Are Not Just Great Balls of Fat 220
Practical Information from Kinetic Data 155
8-6 Lipid-Soluble Vitamins and Their Functions 222
6-5 Examples of Enzyme-Catalyzed Reactions 156
8D BIOCHEMICAL CONNECTIONS NEUROSCIENCE
6-6 Enzyme Inhibition 157 Vision Has Great Chemistry 224
6D BIOCHEMICAL CONNECTIONS MEDICINE 8-7 Prostaglandins and Leukotrienes 228
Enzyme Inhibition in the Treatment of AIDS 163
8E BIOCHEMICAL CONNECTIONS NUTRITION
Summary 164 Why Should We Eat More Salmon? 229
Review Exercises 164 HOT TOPIC The Science of Happiness and Depression 231
Further Reading 167
Summary 236
Review Exercises 237
7 The Behavior of Proteins: Enzymes, Further Reading 238
Mechanisms, and Control 168
7-1 Behavior of Allosteric Enzymes 168
7-2 The Concerted and Sequential Models for Allosteric 9 Nucleic Acids: How Structure
Enzymes 172 Conveys Information 239
7A BIOCHEMICAL CONNECTIONS MEDICINE 9-1 Levels of Structure in Nucleic Acids 239
Allosterism: Drug Companies Exploit the Concept 175 9-2 The Covalent Structure of Polynucleotides 239
7-3 Control of Enzyme Activity by Phosphorylation 176 9A BIOCHEMICAL CONNECTIONS LAW
7B BIOCHEMICAL CONNECTIONS MEDICINE Who Owns Your Genes? 244
An Ancient Drug Works by Stimulating a Protein Kinase 178 9-3 The Structure of DNA 245
7-4 Zymogens 179 9B BIOCHEMICAL CONNECTIONS GENETICS
7-5 The Nature of the Active Site 180 The Human Genome Project: Treasure or Pandora’s Box? 252
7C BIOCHEMICAL CONNECTIONS ALLIED HEALTH 9-4 Denaturation of DNA 253
Families of Enzymes: Proteases 182 9-5 The Principal Kinds of RNA and Their Structures 254
7-6 Chemical Reactions Involved in Enzyme Mechanisms 185 9-6 Roles for RNA 256
7-7 The Active Site and Transition States 188 9-7 RNA and Medical Applications 260
7D BIOCHEMICAL CONNECTIONS ALLIED HEALTH 9C BIOCHEMICAL CONNECTIONS GENETICS
Catalytic Antibodies against Cocaine 189 Why Identical Twins Are Not Identical 262
7-8 Coenzymes 191 HOT TOPIC The Genetics of Breast Cancer 263
7E BIOCHEMICAL CONNECTIONS ENVIRONMENTAL
Summary 265
TOXICOLOGY
Catalysts for Green Chemistry 193 Review Exercises 266
HOT TOPIC Alzheimer’s Disease 194 Further Reading 268
Contents xi
10 Biosynthesis of Nucleic Acids: 12-3 Amino Acid Activation 353

12-4 Prokaryotic Translation 356
Replication 270
12-5 Eukaryotic Translation 365
10-1 The Flow of Genetic Information in the Cell 270
12B BIOCHEMICAL CONNECTIONS NEUROLOGY
10-2 Replication of DNA 270 Protein Synthesis Makes Memories 368
10-3 DNA Polymerase 273 12-6 Posttranslational Modification of Proteins 370
10-4 Proteins Required for DNA Replication 278 12C BIOCHEMICAL CONNECTIONS GENETICS
10-5 Proofreading and Repair 282 Silent Mutations Are Not Always Silent 371
10A BIOCHEMICAL CONNECTIONS GENETICS 12D BIOCHEMICAL CONNECTIONS BIOPHYSICAL
Why Does DNA Contain Thymine and Not Uracil? 287 CHEMISTRY
10-6 DNA Recombination 288 Chaperones: Preventing Unsuitable Associations 373
10B BIOCHEMICAL CONNECTIONS MICROBIOLOGY 12-7 Protein Degradation 374
The SOS Response in E. coli 290 12E BIOCHEMICAL CONNECTIONS PHYSIOLOGY
10-7 Eukaryotic DNA Replication 291 How Do We Adapt to High Altitude? 375
10C BIOCHEMICAL CONNECTIONS ALLIED HEALTH Summary 376
Telomerase and Cancer 295 Review Exercises 377
10D BIOCHEMICAL CONNECTIONS EVOLUTIONARY Further Reading 379
BIOLOGY
Self-Replicating RNAs 296
13 Nucleic Acid Biotechnology
Summary 297 Techniques 380
13-1 Purification and Detection of Nucleic Acids 380
Further Reading 299
13-2 Restriction Endonucleases 382
13-3 Cloning 385
11 Transcription of the Genetic Code: 13-4 Genetic Engineering 391
The Biosynthesis of RNA 300 13A BIOCHEMICAL CONNECTIONS PLANT SCIENCE
11-1 Overview of Transcription 300 Genetic Engineering in Agriculture 392
11-2 Transcription in Prokaryotes 300 13B BIOCHEMICAL CONNECTIONS ALLIED HEALTH
11-3 Transcription Regulation in Prokaryotes 306 Human Proteins through Genetic Recombination Techniques 396
11A BIOCHEMICAL CONNECTIONS BACTERIOLOGY 13-5 DNA Libraries 398
Riboswitches Provide Another Weapon against Pathogens 315 13C BIOCHEMICAL CONNECTIONS ANALYTICAL
11-4 Transcription in Eukaryotes 316 CHEMISTRY (CHROMATOGRAPHY)
Fusion Proteins and Fast Purifications 399
11-5 Transcription Regulation in Eukaryotes 321
11-6 Noncoding RNAs 326 13-6 The Polymerase Chain Reaction 401
13-7 DNA Fingerprinting 404
11B BIOCHEMICAL CONNECTIONS MEDICINE
A Micro RNA Helps Regenerate Nerve Synapses after Injury 329 13D BIOCHEMICAL CONNECTIONS FORENSICS
CSI: Biochemistry—Forensic Uses of DNA Testing 408
11-7 Structural Motifs in DNA-Binding Proteins 330
11-8 Posttranscriptional RNA Modifications 333 13-8 Sequencing DNA 408
11-9 Ribozymes 338 13-9 Genomics and Proteomics 410
HOT TOPIC CRISPR 415
HOT TOPIC Epigenetics 340
Summary 342 Summary 417
Review Exercises 344 Review Exercises 419
Further Reading 345 Further Reading 420
12 Protein Synthesis: Translation of the 14 Viruses, Cancer, and

Genetic Message 347 Immunology 422
14-1 Viruses 422
12-1 Translating the Genetic Message 347
14-2 Retroviruses 427
12-2 The Genetic Code 347
14A BIOCHEMICAL CONNECTIONS MEDICINE
12A BIOCHEMICAL CONNECTIONS VIROLOGY Viruses Are Used for Gene Therapy 428
Influenza A Virus Alters the Reading Frame to Lower Its
Morbidity 352
xii Contents
14-3 The Immune System 429 16-3 Some Important Oligosaccharides 504
14B BIOCHEMICAL CONNECTIONS MEDICINE 16C BIOCHEMICAL CONNECTIONS NUTRITION
The First Vaccine: Bad Science Gone Good 430 Lactose Intolerance: Why Do So Many People Not Want
14C BIOCHEMICAL CONNECTION VIROLOGY to Drink Milk? 506
Viral RNAs Outwit the Immune System 442 16-4 Structures and Functions of Polysaccharides 507
14-4 Cancer 442 16D BIOCHEMICAL CONNECTIONS ALLIED HEALTH
14D BIOCHEMICAL CONNECTIONS GENETICS Why Is Dietary Fiber So Good for You? 508
Cancer: The Dark Side of the Human Genome 443 16-5 Glycoproteins 514
14E BIOCHEMICAL CONNECTIONS BIOTECHNOLOGY 16E BIOCHEMICAL CONNECTIONS ALLIED HEALTH
Nanotech Tackles Cancer 450 Glycoproteins and Blood Transfusions 515
14F BIOCHEMICAL CONNECTIONS IMMUNOLOGY Summary 516
AND ONCOLOGY Review Exercises 517
Attacking the Symptoms Instead of the Disease? 451
Further Reading 519
14-5 AIDS 452
HOT TOPIC Stem Cells: Science and Politics 457
17 Glycolysis 520
Summary 462
17-1 The Overall Pathway of Glycolysis 520
17A BIOCHEMICAL CONNECTIONS ENVIRONMENTAL
Further Reading 465 SCIENCE
Biofuels from Fermentation 521
15 The Importance of Energy 17-2 Conversion of Six-Carbon Glucose to Three-Carbon
Changes and Electron Transfer in Glyceraldehyde-3-Phosphate 524
Metabolism 467 17B BIOCHEMICAL CONNECTIONS ALLIED HEALTH
15-1 Standard States for Free-Energy Changes 467 Dolphins as a Model for Humans with Diabetes 528
15-2 A Modified Standard State for Biochemical 17-3 Glyceraldehyde-3-Phosphate Is Converted to

Applications 470 Pyruvate 531
15-3 The Nature of Metabolism 471 17-4 Anaerobic Metabolism of Pyruvate 538
15A BIOCHEMICAL CONNECTIONS THERMODYNAMICS 17C BIOCHEMICAL CONNECTIONS ALLIED HEALTH
Living Things Are Unique Thermodynamic Systems 471 (Dentistry)
What Is the Connection between Anaerobic Metabolism and
15-4 The Role of Oxidation and Reduction in Dental Plaque? 539
Metabolism 472
17D BIOCHEMICAL CONNECTIONS ALLIED HEALTH
15-5 Coenzymes in Biologically Important Oxidation- Fetal Alcohol Syndrome 542
Reduction Reactions 473
17E BIOCHEMICAL CONNECTIONS CANCER RESEARCH
15-6 Coupling of Production and Use of Energy 477 Using Pyruvate Kinase Isozymes to Treat Cancer 543
15B BIOCHEMICAL CONNECTIONS PHYSIOLOGY 17-5 Energy Production in Glycolysis 543
ATP in Cell Signaling 480
17-6 Control of Glycolysis 544
15-7 Coenzyme A in Activation of Metabolic
Pathways 483 Summary 547
Summary 486
Further Reading 549
Further Reading 489
18 Storage Mechanisms and Control
16 Carbohydrates 490 in Carbohydrate Metabolism 550
16-1 Sugars: Their Structures and Stereochemistry 490 18-1 How Glycogen Is Degraded and Produced 550
16A BIOCHEMICAL CONNECTIONS NUTRITION AND 18A BIOCHEMICAL CONNECTIONS EXERCISE
HEALTH PHYSIOLOGY
Low-Carbohydrate Diets 495 Why Do Athletes Go in for Glycogen Loading? 552
16-2 Reactions of Monosaccharides 498 18-2 Gluconeogenesis Produces Glucose from
16B BIOCHEMICAL CONNECTIONS NUTRITION Pyruvate 557
Vitamin C is Related to Sugars 499 18-3 Control of Carbohydrate Metabolism 562
Contents xiii
18-4 Glucose Is Sometimes Diverted through the Pentose HOT TOPIC What Does Brown Adipose Tissue Have to Do
Phosphate Pathway 570 with Obesity? 629
18B BIOCHEMICAL CONNECTIONS ALLIED HEALTH Summary 631
The Pentose Phosphate Pathway and Hemolytic Anemia 573
Summary 575 Further Reading 634
Further Reading 577 21 Lipid Metabolism 636
19 The Citric Acid Cycle 578 21-1 Lipids Are Involved in the Generation and Storage
of Energy 636
19-1 The Central Role of the Citric Acid Cycle in 21-2 Catabolism of Lipids 636
Metabolism 578
21-3 The Energy Yield from the Oxidation of Fatty
19-2 The Overall Pathway of the Citric Acid Cycle 578 Acids 641
19-3 How Pyruvate is Converted to Acetyl-CoA 580 21-4 Catabolism of Unsaturated Fatty Acids and Odd-
19-4 The Individual Reactions of the Citric Acid Cycle 584 Carbon Fatty Acids 643
19A BIOCHEMICAL CONNECTIONS TOXICOLOGY 21-5 Ketone Bodies 646
Fluorine Compounds and Carbohydrate Metabolism 586 21-6 Fatty Acid Biosynthesis 647
19B BIOCHEMICAL CONNECTIONS LABELING METHODS 21A BIOCHEMICAL CONNECTIONS GENE EXPRESSION
What Is the Origin of the CO2 Released by the Citric Acid Transcription Activators in Lipid Biosynthesis 647
Cycle? 588
21B BIOCHEMICAL CONNECTIONS NUTRITION
19-5 Energetics and Control of the Citric Acid Cycle 593 Acetyl-CoA Carboxylase—A New Target in the Fight against
19-6 The Glyoxylate Cycle: A Related Pathway 596 Obesity 650
19-7 The Citric Acid Cycle in Catabolism 597 21C BIOCHEMICAL CONNECTIONS GENETICS
19-8 The Citric Acid Cycle in Anabolism 598 A Gene for Obesity 655
19C BIOCHEMICAL CONNECTIONS EVOLUTION 21-7 Synthesis of Acylglycerols and Compound Lipids 655
Why Can’t Animals Use All the Same Energy Sources as Plants 21-8 Cholesterol Biosynthesis 659
and Bacteria? 599
21D BIOCHEMICAL CONNECTIONS ALLIED HEALTH
19D BIOCHEMICAL CONNECTION NUTRITION Atherosclerosis 667
Why Is It So Hard to Lose Weight? 602
21-9 Hormonal Control of Appetite 669
19-9 The Link to Oxygen 604
Summary 671
Summary 605 Review Exercises 672
Review exercises 607 Further Reading 673
Further Reading 608
Electron Transport and Oxidative 22 Photosynthesis 675

20 22-1 Chloroplasts Are the Site of Photosynthesis 675
Phosphorylation 609
22A BIOCHEMICAL CONNECTIONS PHYSICS
20-1 The Role of Electron Transport in Metabolism 609 The Relationship between Wavelength and Energy of Light 678
20-2 Reduction Potentials in the Electron Transport 22-2 Photosystems I and II and the Light Reactions of
Chain 610 Photosynthesis 679
20-3 Organization of Electron Transport Complexes 613 22-3 Photosynthesis and ATP Production 685
20-4 The Connection between Electron Transport 22-4 Evolutionary Implications of Photosynthesis with
and Phosphorylation 620 and without Oxygen 686
20-5 The Mechanism of Coupling in Oxidative 22B BIOCHEMICAL CONNECTIONS APPLIED GENETICS
Phosphorylation 622 Improving the Yield of Antimalarial Plants 688
20-6 Shuttle Mechanisms 625 22-5 Dark Reactions of Photosynthesis Fix CO2 688
20A BIOCHEMICAL CONNECTIONS ALLIED HEALTH 22C BIOCHEMICAL CONNECTIONS AGRICULTURE
Sports and Metabolism 627 Plants Feed Animals—Plants Need Energy—Plants Can
20-7 The ATP Yield from Complete Oxidation Produce Energy 688
of Glucose 628 22D BIOCHEMICAL CONNECTIONS GENETICS
Chloroplast Genes 694
xiv Contents
22-6 CO2 Fixation in Tropical Plants 695

24 Integration of Metabolism:
Summary 697 Cellular Signaling 732
24-1 Connections between Metabolic Pathways 732
Further Reading 699
24A BIOCHEMICAL CONNECTIONS ALLIED HEALTH
Alcohol Consumption and Addiction 733
23 The Metabolism of Nitrogen 701 24-2 Biochemistry and Nutrition 734
23-1 Nitrogen Metabolism: An Overview 701 24B BIOCHEMICAL CONNECTIONS NUTRITION
23-2 Nitrogen Fixation 702 Iron: An Example of a Mineral Requirement 737
23A BIOCHEMICAL CONNECTIONS PLANT SCIENCE 24-3 Hormones and Second Messengers 741
Why Is the Nitrogen Content of Fertilizers So Important? 704 24-4 Hormones and the Control of Metabolism 749
23-3 Feedback Inhibition in Nitrogen Metabolism 704 24C BIOCHEMICAL CONNECTIONS NUTRITION
23-4 Amino Acid Biosynthesis 705 Insulin and Low-Carbohydrate Diets 751
23-5 Essential Amino Acids 713 24-5 Insulin and Its Effects 752
23-6 Amino Acid Catabolism 713 24D BIOCHEMICAL CONNECTIONS ALLIED HEALTH
23B BIOCHEMICAL CONNECTIONS PHYSIOLOGY A Workout a Day Keeps Diabetes Away? 754
Water and the Disposal of Nitrogen Wastes 715 24E BIOCHEMICAL CONNECTIONS ALLIED HEALTH
23-7 Purine Biosynthesis 718 Insulin, Diabetes, and Cancer 755
23-8 Purine Catabolism 721 HOT TOPIC G-Protein–Coupled Receptors 757
23-9 Pyrimidine Biosynthesis and Catabolism 723 Summary 761
23-10 Conversion of Ribonucleotides to Review Exercises 762
Deoxyribonucleotides 726 Further Reading 764
23-11 Conversion of dUDP to dTTP 727
23C BIOCHEMICAL CONNECTIONS MEDICINE Answers to Review Exercises A-1
Chemotherapy and Antibiotics—Taking Advantage of the
Need for Folic Acid 728 Index I-1
Summary 728
Further Reading 731
Preface
T his text is intended for students in any field of science or engineering who
want a one-semester introduction to biochemistry but who do not intend to
be biochemistry majors. Our main goal in writing this book is to make bio-
chemistry as clear and applied as possible and to familiarize science students with
the major aspects of biochemistry. For students of biology, chemistry, physics, geol-
ogy, nutrition, sports physiology, and agriculture, biochemistry impacts greatly on
the content of their fields, especially in the areas of medicine and biotechnology.
For engineers, studying biochemistry is especially important for those who hope
to enter a career in biomedical engineering or some form of biotechnology.
Students who will use this text are at an intermediate level in their studies.
A beginning biology course, general chemistry, and at least one semester of
organic chemistry are assumed as preparation.
What’s New
All textbooks evolve to meet the interests and needs of students and instructors
and to include the most current information. Several changes mark this edition.
Biochemistry Hot Topics These articles are

now conveniently located within the relevant chapters.
They highlight new breakthroughs and topics in the area HOT
of biochemistry such as CRISPR, Alzheimer’s disease, TOPIC CRISPR
epigenetics, brown fat, and more!
M
G enetic engineering is the process
by which scientists use biotech-
(2) site-directed zinc finger nucleases;
and (3) TAL effector nucleases. This
plasmids. CRISPR was first described in
1987 and fundamental research was per-
nology to manipulate the DNA of an segment will focus on the most recent, formed on the genome editing approach
organism by introducing/eliminating powerful, broadly applicable, and poten- up until a major breakthrough in 2012,
Updated Coverage Each chapter in the

genes or inserting/deleting mutations to tially impactful of these biotechnological when it was demonstrated that CRISPR/
achieve desired traits. One example of advancements: the CRISPR/Cas9 ge- Cas9 RNA-guided DNA endonuclease
genetic engineering introduced earlier in nome editing technique. Although effec- could be applied to mediate site-specific
UPDATED
text has been updated with the current this chapter is the Simplot Innate potato.
Researchers at J. R. Simplot Co. inserted
tive, site-directed zinc finger nucleases
have been limited in their utility due to
genome engineering in eukaryotic cells
including human cells. Since 2012, well
developments and scientific findings in genes from the wild potato into the ge-
nome of the Innate potato to eliminate
difficulties in the design of proteins that
target a DNA locus of interest, and TAL
over 1,000 studies have been published
in the scientific literature and the fun-
the production of enzymes that cause effector nucleases are challenged due to damental research on in vitro model
the biochemistry field. browning and bruising. The three most design, synthesis, and validation of pro- systems has shifted to in vivo mammal
common methods that scientists use to teins required as engineered nucleases. testing. To understand how genome
edit a genome are (1) clustered, regularly CRISPR/Cas9 is an RNA-based ge- editing with the CRISPR/Cas9 method
interspaced, short palindromic repeat nome editing strategy employing the works, let’s first begin with the four key
technology in combination with the Cas9 same cellular machinery used by bacte- components of the system CRISPR, Cas9,
RNA-guided nuclease (CRISPR/Cas9); ria to afford them immunity to viruses or sgRNA, and PAM (Table 13.2).
New Design and Updated Art
Table 13.2 Components of the CRISPR/Cas9 genome editing system.
Illustrations throughout the text Acronym Spelled out Significance Image
have been redrawn for improved CRISPR Clustered Loci on DNA that can serve as gene cas genes
Leader
Regularly insertion or deletion positions
consistency. In conjunction with the
consistency Interspaced
Palindromic
Repeat-spacer
array
Repeats
book’s updated art program, a more
Ramon Andrade 3D Ciencia/Science
contemporary design and color palette CRISPR associated Nuclease for cutting DNA
have been utilized.
Cas9
protein 9 (Cas 1 . . . 10 exist)
Photo Library
sgRNA Single guide A construct/chimera of CRISPR RNA sgRNA (single guide RNA)
ribonucleic acid (crRNA) and trans-activating CRISPR
RNA (tracrRNA); contains sequence
Further Reading An annotated information for insertion/deletion
bibliography is now provided in the Target-specific

crRNA sequence
tracrRNA
Further Reading section at the end of PAM Protospacer sgRNA binds to a target gene locus next S. pyogenes: NGG
each chapter
chapter, making these resources
adjacent motif to PAM; sequence NGG (any, guanine,
guanine) in S. pyogenes or 5’-NAG (any, Human: 5’-NAG
adenine, guanine) in humans
more easily accessible to the student. CRISPR - https://en.wikipedia.org/wiki/CRISPR [simplified view from Horvath, P. and R. Barrangou Science 327, 167 (2010)]; Cas9 - Jinek et al. Science 343,
6167 (2014); sgRNA - www.clontech.com/US/Productsme_Editing/CRISPR_cas9/Ress/Designing_sgRNA
HT-415
xv
xvi Preface
Table of Changes by Chapter

T
Chapter 1 Added summary of major types of biomolecules in combination with the Cas9 RNA-guided
nuclease (CRISPR/Cas9) method of genetic
Chapter 3 Expanded Biochemical Connection on oxytocin engineering, example of CRISPR/Cas9 to
and its social effects, added four new Review
engineer Innate potato
Exercises
Chapter 14 Updated content on vaccine development for
Chapter 4 Updated Biochemical Connection on prion Ebola and advances in stem cell research
diseases, added Hot Topic about aging
Chapter 16 New research findings that correlate the use
Chapter 6 Updated Biochemical Connection on enzyme of artificial sweeteners to gut microbiome,
markers for diseases
suggesting the reason diet products may not
Chapter 7 Added new Hot Topic on Alzheimer’s disease, result in weight loss
added four new Review Exercises
Chapter 17 Updated content associated with biofuels
Chapter 8 Added expanded Hot Topic on happiness and Chapter 19 New information on the use of the compound
depression, added two new Review Exercises
1080 (sodium fluoroacetate) for control of
Chapter 9 Added Hot Topic on breast cancer, added mammal populations in New Zealand
material on long noncoding RNA, added new
Chapter 20 Added a new Hot Topic on brown fat to include
section on medical applications of RNA, deleted
recent research developments demonstrating the
Biochemical Connection on synthetic genome
benefits of brown adipose tissue to maintenance
Chapter 10 Added brief mention of replication termination of healthy metabolism
Chapter 11 Added new Hot Topic on epigenetics, deleted Chapter 24 Added updated Hot Topic on G-protein–
Biochemical Connections box about CREB, coupled receptors to include recent research
deleted Biochemical Connections about on the biased agonism or functional selectivity
epigenetics and cancer model associated with opioid receptors
Chapter 13 Added new Hot Topic on clustered, regularly
interspaced, short palindromic repeat technology
Hormone
Receptor Plasma membrane
Proven Features
Adenylate cyclase Adipose cell
P P
ATP
AT cAMP
Protein kinase Protein kinase

Visual Impact Ideal for visual learners, this book’s state-of-the-art approach
helps students visualize key processes and understand important topics.
(inactive) (active)
ATP
AT ADP
Triacylglycerol
Triacylglycerol
lipase (inactive) Triacylglycerol
lipase (active) Fatty acid
Biochemical Connections The Biochemical Connections highlight special

P
P
Diacylglycerol
Phosphatase DAG
lipase
topics of particular interest to students. Topics frequently have clinical

Fatty acid
implications, such as cancer, AIDS, and nutrition. These essays help students
Monoacylglycerol
MAG
make the connection between biochemistry and the real-world. They are
lipase
Fatty acid
Glycerol
flowed in with the narrative and are placed exactly where they need to be
read in each chapter. And although they have a different
presentation than the rest of the narrative, they are meant to
be read with the narrative and should not be skipped. They are
12B BIOCHEMICAL CONNECTIONS like crescendos in classical music—the change in tempo from
the usual narrative to the unique visual presentation and voice
Neurology of the Biochemical Connections prevents the student’s level
of interest from dipping—students are always engaged. See a
Protein Synthesis Makes Memories
full listing of Biochemical Connections boxes in the Table of
Contents.
Apply Your Knowledge The Apply Your Knowledge boxes are interspersed
within chapters and are designed to provide students with problem-solving
2.1 APPLY YOUR KNOWLEDGE
experience. The topics chosen are areas of study where students usually have
the most difficulty. Solutions and problem-solving strategies are included,
pH Calculations
giving examples of the problem-solving approach for specific material.
Preface xvii
Marginal Glossary No flipping back and forth to read full definitions of key
titration an experiment in which a measured
terms. Terms are defined in the margins. amount of base is added to an acid
Early Inclusion of Thermodynamics Select material on thermodynamics

appears early in the text. Chapter 1 includes sections on energy and change,
spontaneity in biochemical reactions, and life and thermodynamics. Also,
Chapter 4 contains an extended section on protein-folding dynamics. We
feel it is critical that students understand the driving force of biological
© agsandrew/Shutterstock.com
processes and see that so much of biology (protein folding, protein–protein DSuniv.0
interactions, small molecule binding, etc.) is driven by the favorable
disordering of water molecules.
Summaries and Questions Each chapter closes with a concise

summary, a broad selection of questions, and an annotated
bibliography that suggests sources for further reading. The Review
Exercises fall into four categories: RECALL, REFLECT AND APPLY
L , BIOCHEMICAL
LY
CONNECTIONS, and MATHEMATICAL. The RECALL questions are designed for
students to quickly assess their mastery of the material, and the REFLECT AND
L questions are for students to work through more thought-provoking
APPLY
LY
questions. BIOCHEMICAL CONNECTIONS questions test students on the BIOCHEMICAL
CONNECTIONS essays in that chapter. The MATHEMATICAL questions are
quantitative in nature and focus on calculations.
Organization
Because biochemistry is a multidisciplinary science, the first task in presenting
it to students of widely varying backgrounds is to put it in context. The text is
organized into four categories. The first provides the necessary background
and connects biochemistry to other sciences. The next focuses on the structure Astronomy
and dynamics of important cellular components. This is followed by molecular
biology and then intermediary metabolism.
Chapters 1 & 2: Background and Connections

● Relationship between biochemistry and other sciences, particularly Geology Biochemistry Physics
concerning the origins of life
● Organic functional groups in the context of biochemistry
● Link between biochemistry and biology, especially the distinction
between prokaryotes and eukaryotes and the role of organelles in
eukaryotes Biology
● Biochemical view of buffers, solvent properties of water, and other
familiar general chemistry topics
xviii Preface
Chapters 3-8: Structure and

Dynamics of Cellular Components
● Amino acids, peptides, the structure
and action of proteins, including
© molekuul_be/Shutterstock.com
enzyme catalysis
● Thermodynamics, hydrophobic
interactions
● Techniques for isolating and
studying proteins
● Enzyme kinetics and mechanisms
● Structure of membranes and their
lipid components
Chapters 9-14: Molecular Biology

● Replication of DNA
● Transcription and gene regulation
● Biosynthesis of nucleic acids
● Translation of the genetic message and protein synthesis
© David Carillet/Shutterstock.com
● Biotechnology techniques
● Viruses, cancer, and immunology
Chapters 15-24: Intermediary Metabolism

● Thermodynamic concepts applied specifically to biochemical topics such as
coupled reactions
● Connection between metabolism and electron transfer (oxidation–
reduction) reactions
● Coenzymes
● Overview of the metabolic pathways: glycolysis
● Glycogen metabolism, gluconeogenesis, and the pentose phosphate
pathway
© Ashray Shah/Shutterstock.com
● Citric acid cycle, electron transport chain, and oxidative phosphorylation

● Catabolic and anabolic aspects of lipid metabolism
● Photosynthesis and carbohydrate metabolism
● Plant origin of antimalarials
● Metabolism of nitrogen-containing compounds such as amino acids,
porphyrins, and nucleobases
● Integrated look at metabolism, including a treatment of hormones and
second messengers
● Nutrition
● Immune system
Some topics such as enzymes and the biosynthesis of nucleic acids are
split into two chapters to give students ample time to fully understand the
concepts involved. Some are discussed several times, such as the control of
carbohydrate metabolism. Subsequent discussions make use of and build on
information students have already learned. It is particularly useful to return
to a topic after students have had time to assimilate and reflect on it.
This text gives an overview of important topics of interest to biochemists
and shows how the remarkable recent progress of biochemistry impinges on
other sciences. The length is intended to provide instructors with a choice of
favorite topics without being overwhelming for the limited amount of time
available in one semester.
Preface xix
Alternative Teaching
T Options
The order in which individual chapters are covered can be changed to suit the
needs of specific groups of students. Although we prefer an early discussion
of thermodynamics, the portions of Chapters 1 and 4 that deal with thermo-
dynamics can be covered at the beginning of Chapter 15. All of the molecular
biology chapters (Chapters 9 through 14) can precede metabolism or can fol-
low it, depending on the instructor’s choice. The order in which the material
on molecular biology is treated can be varied according to the preference of
the instructor.
Alternate Editions
Loose-Leaf Edition for Biochemistry 9e
ISBN: 978-1-305-96195-1
A loose-leaf (unbound, three-hole-punched) version of Biochemistry 9e, which
can be inserted in a binder, is also available.
Acknowledgments
We would like to acknowledge colleagues who contributed their ideas and
critiques of the manuscript. Some reviewers responded to specific queries
regarding the text itself. We thank them for their efforts and their helpful
suggestions.
Reviewers Acknowledgments
Ninth Edition Reviewers
Paul Adams, University of Kansas
Kenneth Balazovich, University of Michigan
Tory Hagen, Oregon State University
Marcy Henrick, Appalachian College of Pharmacy
Deborah Heyl-Clegg, Eastern Michigan University
Eighth Edition Reviewers
Kenneth Balazovich, PhD, University of Michigan
Laurent Dejean, California State University at Fresno
Marcy Hernick, Virginia Tech
Holly Huffman, Arizona State University
Mark Kearley, Florida State University
James Knopp, North Carolina State University
Paul Larsen, University of California–Riverside
Gerry Prody, Western Washington University
Sandra Turchi, Millersville University
Seventh Edition Reviewers
Paul D. Adams, University of Kansas
Dan Davis, University of Arkansas
Nick Flynn, Angelo State University
Denise Greathouse, University of Arkansas
James R. Paulson, University of Wisconsin–Oshkosh
Kerry Smith, Clemson University
Alexandre G. Volkov, Oakwood University
We would also like to thank the people at Cengage Learning, who were essen-
tial to the development of this book: Theresa Dearborn, content developer;
Teresa Trego, senior content project manager; Maureen Rosener, product
xx Preface
manager; and Dawn Giovanniello, product director. Thank you, Christine

Myaskovsky, our intellectual property analyst, and Kathryn Kucharek, our intel-
lectual property project manager, at Cengage. We also thank Marketing Man-
ager Ana Albinson, Content Developer Elizabeth Woods, and Product Assistant
Kristina Cannon.
Lynn Lustberg of MPS Limited served as our project manager. Photo and
text research was performed by Rupesh Kumar Jayakumar, Manojkiran Chan-
der, and Rashmi Manoharan of Lumina Datamatics.
Supporting Materials
Please visit http://www.cengage.com/chemistry/campbell/biochemistry9e for
information about student and instructor resources for this text.
A Final Note from Shawn Farrell

I cannot adequately convey how impossible this project would have been with-
out my wonderful family, who put up with a husband and father who became a
hermit in the back office. I would also like to thank David Hall, book represen-
tative, for starting me down this path, and the late John Vondeling for giving
me an opportunity to expand into other types of books and projects.
I met Mary Campbell in the mid-1990s when I was asked to collaborate on
the fourth edition of this textbook with her. She was a fascinating individual
and a visionary in this field. She believed that biochemistry should be acces-
sible not only to the hard-core chemistry and biochemistry majors, but also to
the wide range of majors that embrace biochemistry. Such was her inspiration
for this one-semester text. She was very generous with her time and helped me
immensely during the process of writing our first edition together. She also
had a rapier wit and was a hoot to hang out with at science conventions. Her
sudden passing in May 2014 was a shock to us all, and she will be sorely missed.
A Final Note from Owen McDougal

I wish to thank my wife Lynette for her patience and support, may the road rise
to meet you…, my children McKenzie and Riley for reminding me where my
priorities belong, and my parents Bob and Bobbie for unconditional support
and inspiration to be all I can be.
Chapter Outline
1-1 Basic Themes 1
1
Biochemistry and Life 1
Origin of Life on Earth 2
1-2 Chemical Foundations of Biochemistry 2
Biochemistry and the
Amino Acids 2
Carbohydrates 3
Nucleotides 4
Organization of Cells
Lipids 4
Functional Groups Important in Biochemistry 4
1-3 The Beginnings of Biology 6
The Earth and Its Age 6 1-1 Basic Themes
Biomolecules 8
Molecules to Cells 12 Biochemistry and Life
1-4 The Biggest Biological Distinction— c How does biochemistry describe life processes?
Prokaryotes and Eukaryotes 16
Prokaryotic Cells 17
Living organisms, such as humans, and even the individual cells of
Eukaryotic Cells 18 which they are composed, are enormously complex and diverse.
Nevertheless, certain unifying features are common to all living
1-5 How We Classify Eukaryotes
things from the simplest bacterium to the human being. They all
and Prokaryotes 21
Five-Kingdom Classification System 22 use the same types of biomolecules, and they all use energy. As a result,
1A BIOCHEMICAL CONNECTIONS
organisms can be studied via the methods of chemistry and physics.
BIOTECHNOLOGY Extremophiles: The Toast Biochemistry can be defined in many ways. From the name, it is
of the Industry 23 clear it is the chemistry of life. It combines biology and chemistry,
Three-Domain Classification System 23 and any given instructor may have more of a biology focus, a chemis-
Eukaryotic Origins 23 try focus, or anything in between.
1-6 Biochemical Energetics 25 Disciplines that appear to be unrelated to biochemistry can pro-
Thermodynamic Principles 25 vide answers to important biochemical questions. For example, the
Energy Changes 26 magnetic resonance imaging (MRI) tests that play an important role
Spontaneity in Biochemical Reactions 26 in the health sciences originated with physicists, became a vital tool
Life and Thermodynamics 27
for chemists, and currently play a large role in biochemical research.
1B BIOCHEMICAL CONNECTIONS The field of biochemistry draws on many disciplines, and its multidis-
THERMODYNAMICS Predicting Reactions 28
ciplinary nature allows it to use results from many sciences to answer
questions about the molecular nature of life processes. Important applica-
tions of this kind of knowledge are made in medically related fields;
an understanding of health and disease at the molecular level leads
to more effective treatment of illnesses of many kinds.
The activities within a cell are similar to the transportation sys-
tem of a city. The cars, buses, and taxis correspond to the mole-
cules involved in reactions (or series of reactions) within a cell. The
routes traveled by vehicles likewise can be compared to the reac-
tions that occur in the life of the cell. Note particularly that many
vehicles travel more than one route—for instance, cars and taxis
can go almost anywhere—whereas other, more specialized modes
of transportation, such as subways and streetcars, are confined to
single paths. Similarly, some molecules play multiple roles, whereas
others take part only in specific series of reactions. Also, the routes
operate simultaneously, and we shall see that this is true of the many
reactions within a cell.
To continue the comparison, the transportation system of a
large city has more kinds of transportation than does a smaller
2 CHAPTER 1 Biochemistry and the Organization of Cells
one. Although a small city may have only cars, buses, and taxis, a large city
may have all of these plus others, such as streetcars or subways. Analogously,
some reactions are found in all cells, and others are found only in specific
kinds of cells. Also, more structural features are found in the larger, more
complex cells of larger organisms than in the simpler cells of organisms such
as bacteria.
An inevitable consequence of this complexity is the large quantity of
terminology that is needed to describe it; learning considerable new vocabu-
lary is an essential part of the study of biochemistry. You will also see many
cross-references in this book, which reflect the many connections among the
processes that take place in the cell.
Origin of Life on Earth

The fundamental similarity of cells of all types makes speculating on the origins
of life a worthwhile question. How did the components of our bodies come to
be and to do the things that they do? What are the molecules of life? Even the
structures of comparatively small biomolecules consist of several parts. Large
biomolecules, such as proteins and nucleic acids, have complex structures, and
living cells are enormously more complex. Even so, both molecules and cells must
have arisen ultimately from very simple molecules, such as water, methane, carbon
dioxide, ammonia, nitrogen, and hydrogen (Figure 1.1). In turn, these simple
molecules must have arisen from atoms.
c How did living things originate?

The way in which the Universe itself, and the atoms of which it is com-
posed, came to be is a topic of great interest to astrophysicists as well as
other scientists. Simple molecules were formed by combining atoms, and
reactions of simple molecules led in turn to more complex molecules. The
molecules that play a role in living cells today are the same molecules as
those encountered in organic chemistry; they simply operate in a different
context.
1-2 Chemical Foundations of Biochemistry

organic chemistry the study of compounds of Organic chemistry is the study of compounds of carbon and hydrogen and
carbon, especially of carbon and hydrogen and their derivatives. Because the cellular apparatus of living organisms is made
their derivatives
up of carbon compounds, biomolecules are part of the subject matter of or-
ganic chemistry. Additionally, many carbon compounds are not found in any
organism, and many topics of importance to organic chemistry have little
connection with living things. We are going to concentrate on the aspects
of organic chemistry that we need in order to understand what goes on in
living cells.
The small molecules found in the cell can usually be lumped into four basic
classes. We will see these over and over again during our study of biochemistry.
They are the basic building blocks of life.
Amino Acids
The simplest compounds are the amino acids. They get their name from the
fact that they all contain an amino group and a carboxyl group, as shown in
Figure 1.2. Under physiological conditions both the carboxyl group and amino
group are ionized (-COO2 and –NH3+, respectively). Amino acids can be shown
in various ways, including a structural formula or a ball and stick formula.
Amino acids have a basic structure where a central carbon atom is bonded to
a carboxyl group, an amino group, a hydrogen, and a variable group, called
Body system of organism

Organ
Atoms
Oxygen and
hydrogen
Bone
Tissue
Molecules
H H
Water
Bone tissue
Cell
Macromolecules
Nucleus
Protein Plasma
Golgi membrane Bone cell
Nucleus
Organelles
Mitochondria
Figure 1.1 Levels of structural organization in the human body. Note the hierarchy from simple
to complex. COO2 COO–
1
H 3N C H +
the R group. It is the difference between the R groups that makes each NH3 C
amino acid unique. H
CH3
Carbohydrates L-Alanine
Carbohydrates are compounds made up of carbon, hydrogen, and oxy- CH3
gen, with a general formula of (CH2O)n, where n is at least 3. The sim-
plest forms are called monosaccharides, or sugars. The most common Figure 1.2 Basic structure of the amino acid, alanine.
H O monosaccharide is glucose, which has the formula C 6H 12O 6, as shown in

1 C Figure 1.3. For convenience, sugars are often drawn as a straight chain, but in
2
solution they form cyclic structures. Simple sugars often make up much larger
H C OH polymers and are used for energy storage and structural components.
3
HO C H CH2OH
H
4
C OH H
C O
H Nucleotides
H
5
C
OH H
C Nucleotides are the basic unit of the hereditary materials DNA and RNA. They
H C OH
HO C C OH also form the molecular currency of the cell, adenosine triphosphate (ATP). A
6
CH2OH nucleotide is composed of a five-carbon sugar, a nitrogen-containing ring, and
H OH
one or more phosphate groups. The important nucleotide, ATP, is shown in
D-Glucose -D-Glucopyranose
Figure 1.4. It is composed of the nitrogenous base adenine, the sugar ribose,
Figure 1.3 Straight chain and cyclic depictions and three phosphates.
of glucose, the most common monosaccharide.
Lipids
NH2
The fourth major group of biochemicals consists of lipids. They are the most
Phosphoric anhydride N N diverse and cannot be shown with a simple structure common to all lipids.
linkages However, they all have the common trait that they are poorly soluble in water.
N N This is because most of their structure is composed of long chains of hydrocar-
O O O bons. A simple lipid is palmitic acid, which has 16 carbons. There are several
–O P O P O P O CH2 ways to depict such a lipid, as shown in Figure 1.5.
O Another important lipid you have heard of is cholesterol, shown in
O– O– O–
H H Figure 1.6. It differs considerably in its structure from palmitic acid, but is still
H H very insoluble in water due to the chains of carbon and the fact that it has only
OH OH a single oxygen molecule in it.
ATP c Can a chemist make the molecules of life in a laboratory?

(adenosine-5'-triphosphate)
Until the early part of the 19th century, there was a widely held belief in “vital
Figure 1.4 The structure of ATP, an important
forces,” forces presumably unique to living things. This belief included the idea
nucleotide in energy production.
that the compounds found in living organisms could not be produced in the
laboratory. German chemist Friedrich Wöhler performed the critical experi-
O OH O OH
ment that disproved this belief in 1828. Wöhler synthesized urea, a well-known
C C
waste product of animal metabolism, from ammonium cyanate, a compound
CH2 obtained from mineral (i.e., nonliving) sources.
H2C
NH4OCN S H2NCONH2
CH2
H2C Ammonium Urea
CH2
cyanate
H2C It has subsequently been shown that any compound that occurs in a living
CH2 organism can be synthesized in the laboratory, although in many cases the
H2C synthesis represents a considerable challenge to even the most skilled organic
chemist.
CH2 Palmitic acid The reactions of biomolecules can be described by the methods of organic
H2C
chemistry, which requires the classification of compounds according to their
CH2 functional groups. The reactions of molecules are based on the reactions of their respec-
H2C tive functional groups.
CH2
H2C
Functional Groups Important in Biochemistry
CH3
Table 1.1 lists some biologically important functional groups. Note that most
Figure 1.5 The simple lipid palmitic acid, shown of these functional groups contain oxygen and nitrogen, which are among the
with a structural formula, an abbreviated formula, most electronegative elements. As a result, many of these functional groups
and a space-filling model. are polar, and their polar nature plays a crucial role in their reactivity. Some
functional groups groups of atoms that give rise to groups that are vitally important to organic chemists are missing from the
the characteristic reactions of organic compounds table because molecules containing these groups, such as alkyl halides and acyl
chlorides, do not have any particular applicability in biochemistry. Conversely, CH3

carbon-containing derivatives of phosphoric acid are mentioned infrequently CHCH2CH2CH2CH(CH3)2
H 3C
in beginning courses on organic chemistry, but esters and anhydrides of phos- H
phoric acid (Figure 1.7) are of vital importance in biochemistry. ATP, a mol- H3C H
ecule that is the energy currency of the cell, contains both ester and anhydride
linkages involving phosphoric acid. H H
HO
Important classes of biomolecules have characteristic functional groups
H
that determine their reactions. We shall discuss the reactions of the functional Cholesterol
groups when we consider the compounds in which they occur. Figure 1.6 The structure of cholesterol, an
important lipid in biological membranes.
Table 1.1 Functional Groups of Biochemical Importance

Classof
Class of General Characteristic
Characteristic NameName
of of
Compound
Compound General Structure
Structure Functional Group
Functional Group Functional Group
Functional Group ExampleExample
RCH CH2
RCH CHR
Alkenes C C Double bond CH2 CH2
R2C CHR
R2C CR2
Alcohols ROH OH Hydroxyl group CH3CH2OH
Ethers ROR O Ether group CH3OCH3
RNH2
Amines R2NH N Amino group CH3NH2
R3N
Thiols RSH SH Sulfhydryl group CH3SH
O O O
Aldehydes Carbonyl group
R C H C CH3CH
O O O
Carbonyl group
Ketones R C R C CH3CCH3
O O O
Carboxylic Carboxyl group
acids R C OH C OH CH3COH
O O O
Ester group
Esters R C OR C OR CH3COCH3
O O O
R C NR2 C N Amide group CH3CN(CH3)2
O
Amides
R C NHR
O
R C NH2
O O O
Phosphoric acid Phosphoric ester
R O P OH O P OH CH3 O P OH
esters group
OH OH OH
O O O O O O
Phosphoric acid Phosphoric
R O P O P OH P O P HO P O P OH
anhydrides anhydride group
OH OH OH OH OH OH
O O
HO P OH + HO R HO P O R
1 Reaction of phosphoric acid with a
hydroxyl group to form an ester, which OH H2O OH
contains a P-O-R linkage. Phosphoric Phosphoric acid Alcohol An ester of phosphoric acid
acid is shown in its nonionized form in
this figure. Space-filling models of
phosphoric acid and its methyl ester are
shown. The red spheres represent
oxygen; the white, hydrogen; the green, R
carbon; and the orange, phosphorus.
O O O O
HO P OH + HO P OH HO P O P OH
Reaction of two molecules of phosphoric OH OH H2O OH OH

2
acid to form an anhydride, which Anhydride of phosphoric acid
contains a P-O-P linkage. A space-filling
model of the anhydride of phosphoric
acid is shown.
NH2
Ester
O O O C
N
C N
HO P O P O P O HC
C CH
OH OH OH CH2 O N
N
3 The structure of ATP (adenosine
triphosphate), showing two anhydride C C
linkages and one ester. Anhydride H H
H C C H
OH OH
ATP
Figure 1.7 ATP and the reactions for its formation.
1-3 The Beginnings of Biology

The Earth and Its Age
Although humans in general and science fiction writers in particular are fas-
cinated by the idea of life on other planets, to date, we are aware of only one
planet that unequivocally supports life: our own. The Earth and its waters are
universally understood to be the source and mainstay of life as we know it. A
natural first question is how the Earth, along with the Universe of which it is a
part, came to be.
c How and when did the Earth come to be?

Currently, the most widely accepted cosmological theory for the origin of
the Universe is the big bang, a cataclysmic explosion. According to big-bang
cosmology, all the matter in the Universe was originally confined to a com-
paratively small volume of space. As a result of a tremendous explosion, this
“primordial fireball” started to expand with great force. Immediately after
the big bang, the Universe was extremely hot, on the order of 15 billion
1-3 The Beginnings of Biology 7
(15 3 109) K. (Note that Kelvin temperatures are written without a degree
symbol.) The average temperature of the Universe has been decreasing ever
since as a result of expansion, and the lower temperatures have permitted
the formation of stars and planets. In its earliest stages, the Universe had a
fairly simple composition. Hydrogen, helium, and some lithium (the three
smallest and simplest elements on the periodic table) were present, having
been formed in the original big-bang explosion. The rest of the chemical
elements are thought to have been formed in three ways: (1) by thermonu-
clear reactions that normally take place in stars, (2) in explosions of stars,
and (3) by the action of cosmic rays outside the stars since the formation of
the galaxy. The process by which the elements are formed in stars is a topic of
interest to chemists as well as to astrophysicists. For our purposes, note that
the most abundant isotopes of biologically important elements such as car-
bon, oxygen, nitrogen, phosphorus, and sulfur have particularly stable nuclei.
These elements were produced by nuclear reactions in first-generation stars,
the original stars produced after the beginning of the Universe (Table 1.2).
Many first-generation stars were destroyed by explosions called supernovas,
and their stellar material was recycled to produce second-generation stars,
such as our own Sun, along with our solar system. Radioactive dating, which
uses the decay of unstable nuclei, indicates that the age of the Earth (and the
rest of the solar system) is 4 billion to 5 billion (4 3 109 to 5 3 109) years. The
atmosphere of the early Earth was very different from the one we live in, and
it probably went through several stages before reaching its current composi-
tion. The most important difference is that, according to most theories of
the origins of the Earth, very little or no free oxygen (O2) existed in the early
stages (Figure 1.8). The early Earth was constantly irradiated with ultraviolet
light from the Sun because there was no ozone (O3) layer in the atmosphere
to block it. Under these conditions, the chemical reactions that produced
simple biomolecules took place.
The gases usually postulated to have been present in the atmosphere
of the early Earth include NH3, H2S, CO, CO2, CH4, N2, H2, and (in both
liquid and vapor forms) H2O. However, there is less agreement on the rela-
tive amounts of these components, from which biomolecules ultimately
arose. Many of the earlier theories of the origin of life postulated CH 4 as
Table 1.2 Abundance of Important Elements Relative to Carbon*

Element Abundance in Organisms Abundance in Universe
Hydrogen 80–250 10,000,000
Carbon 1,000 1,000
Nitrogen 60–300 1,600
Oxygen 500–800 5,000
Sodium 10–20 12
Magnesium 2–8 200
Phosphorus 8–50 3
Sulfur 4–20 80
Potassium 6–40 0.6
Calcium 25–50 10
Manganese 0.25–0.8 1.6
Iron 0.25–0.8 100
Zinc 0.1–0.4 0.12
*Each abundance is given as the number of atoms relative to a thousand atoms of carbon.
Figure 1.8 Formation of biomolecules on the early Earth. Conditions on early Earth would
have been inhospitable for most of today’s life. Very little or no oxygen (O2) existed. Volcanoes
erupted, spewing gases, and violent thunderstorms produced torrential rainfall that covered the
Earth. The green arrow indicates the formation of biomolecules from simple precursors.
the carbon source, but more recent studies have shown that appreciable
amounts of CO 2 must have existed in the atmosphere at least 3.8 billion
(3.8 3 109) years ago.
This conclusion is based on geological evidence: The earliest known rocks
are 3.8 billion years old, and they are carbonates, which arise from CO2. Any
NH3 originally present must have dissolved in the oceans, leaving N 2 in the
atmosphere as the nitrogen source required for the formation of proteins and
nucleic acids.
Biomolecules
c How were biomolecules likely to have formed on the early Earth?
Experiments have been performed in which the simple compounds of the
early atmosphere were allowed to react under the varied sets of conditions
that might have been present on the early Earth. The results of such experi-
ments indicate that these simple compounds react abiotically or, as the word
indicates (a, “not,” and bios, “life”), in the absence of life, to give rise to bi-
ologically important compounds such as the components of proteins and
nucleic acids. Of historic interest is the well-known Miller–Urey experiment.
In each trial, an electric discharge, simulating lightning, is passed through
a closed system that contains H 2, CH4, and NH3, in addition to H2O. Simple
organic molecules, such as formaldehyde (HCHO) and hydrogen cyanide
(HCN), are typical products of such reactions, as are amino acids, the build-
ing blocks of proteins. According to one theory, reactions such as these took
place in the Earth’s early oceans; other researchers postulate that such reac-
tions occurred on the surfaces of clay particles that were present on the early
Earth. It is certainly true that mineral substances similar to clay can serve as
catalysts in many types of reactions. Recent theories of the origin of life focus
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78 & 80 King Street East, Toronto.
C. W. COATES, Montreal. S. F. HUESTIS, Halifax, N.S.
Transcriber’s Note (continued)
The many conversations in Scots, along with archaic spelling and

inconsistencies in hyphenation, have been left unchanged except where
noted below. Minor typographical errors have been corrected without
note.
Page 6 – “offhand” changed to “off-hand” (the usual off-hand

remark)
Page 297 – “goodbye” changed to “good-bye” (after bidding good-

bye)
There are a small number of footnotes in the book. Most of these

provide a helpful translation into English of words expressed in Scots.
For that reason, all footnotes have been reindexed and placed
immediately below the paragraph in which they are referenced.
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Biochemistry Shawn O.

Educating Holden Wishing Well Texas 11 1st Edition

Lives in Architecture Terry Farrell 1st Edition Terry

Java Programming Joyce Farrell

Java Programming Joyce Farrell

Criminology of Serial Poisoners Michael Farrell

Integrative Human Biochemistry: A Textbook for Medical

Essential biochemistry Kathleen Cornely

Synoptic Analysis and Forecasting An Introductory

Australia ● Brazil ● Mexico ● Singapore ● United Kingdom ● United States

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To the returning adult students in my classes, especially those with

My recognition and appreciation go to those who saw the potential in me

Summary 137 Summary 198

6 The Behavior of Proteins: 8 Lipids and Proteins Are Associated

10 Biosynthesis of Nucleic Acids: 12-3 Amino Acid Activation 353

12 Protein Synthesis: Translation of the 14 Viruses, Cancer, and

15-2 A Modified Standard State for Biochemical 17-3 Glyceraldehyde-3-Phosphate Is Converted to

Electron Transport and Oxidative 22 Photosynthesis 675

22-6 CO2 Fixation in Tropical Plants 695

Biochemistry Hot Topics These articles are

Updated Coverage Each chapter in the

Further Reading An annotated information for insertion/deletion

bibliography is now provided in the Target-specific

Table of Changes by Chapter

Receptor Plasma membrane

Protein kinase Protein kinase

Biochemical Connections The Biochemical Connections highlight special

topics of particular interest to students. Topics frequently have clinical

Early Inclusion of Thermodynamics Select material on thermodynamics

Summaries and Questions Each chapter closes with a concise

Chapters 1 & 2: Background and Connections

Chapters 3-8: Structure and

Chapters 9-14: Molecular Biology

Chapters 15-24: Intermediary Metabolism

● Citric acid cycle, electron transport chain, and oxidative phosphorylation

manager; and Dawn Giovanniello, product director. Thank you, Christine

A Final Note from Shawn Farrell

A Final Note from Owen McDougal

Origin of Life on Earth

c How did living things originate?

1-2 Chemical Foundations of Biochemistry

Body system of organism

H O monosaccharide is glucose, which has the formula C 6H 12O 6, as shown in

ATP c Can a chemist make the molecules of life in a laboratory?

chlorides, do not have any particular applicability in biochemistry. Conversely, CH3

Table 1.1 Functional Groups of Biochemical Importance

Alcohols ROH OH Hydroxyl group CH3CH2OH

Ethers ROR O Ether group CH3OCH3

Thiols RSH SH Sulfhydryl group CH3SH

Reaction of two molecules of phosphoric OH OH H2O OH OH

1-3 The Beginnings of Biology

c How and when did the Earth come to be?

Table 1.2 Abundance of Important Elements Relative to Carbon*

By the Rev. John Lathern, D.D.

By the Rev. E. Barrass, M.A.

By the Rev. J. Cynddylan Jones.

By the Rev. J. Jackson Wray.

By the Rev. W. H. Withrow, D.D., F.R.S.C.