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The Organic Chemistry Of Biological Pathways

by: McMurry, John E.; BEGLEY, TADHG P.

The Organic Chemistry Of Biological Pathways

by: McMurry, John E.; BEGLEY, TADHG P.

ISBN 13:
9780974707716
ISBN 10:
0974707716
Format: Hardcover
Copyright: 02/11/2005
Publisher: Roberts & Co

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Summary

Intended for advanced undergraduates and graduate students in all areas of biochemistry, The Organic Chemistry of Biological Pathways provides an accurate treatment of the major biochemical pathways from the perspective of mechanistic organic chemistry.

Foreword

Preface

xvii

Reviewers

xix

The Authors

xxi

Common Mechanisms in Biological Chemistry

(42)

Functional Groups in Biological Chemistry

(3)

Acids and Bases; Electrophiles and Nucleophiles

(6)

Bronsted--Lowry Acids and Bases

(4)

Lewis Acids and Bases

(1)

Electrophiles and Nucleophiles

(1)

Mechanisms: Electrophilic Addition Reactions

(2)

Mechanisms: Nucleophilic Substitution Reactions

(3)

Mechanisms: Nucleophilic Carbonyl Addition Reactions

(9)

Nucleophilic Addition Reactions

(2)

Alcohol Formation

(1)

Imine (Schiff Base) Formation

(2)

Acetal Formation

(2)

Conjugate (1,4) Nucleophilic Additions

(2)

Mechanisms: Nucleophilic Acyl Substitution Reactions

(2)

Mechanisms: Carbonyl Condensation Reactions

(4)

Mechanisms: Elimination Reactions

(2)

Oxidations and Reductions

(9)

Problems

(6)

Biomolecules

(50)

Chirality and Biological Chemistry

(8)

Enantiomers

(2)

Diastereomers, Epimers, and Meso Compounds

(3)

Prochirality

(2)

Biomolecules: Lipids

(4)

Triacylglycerols

(2)

Other Lipids: Terpenoids, Steroids, and Prostaglandins

(2)

Biomolecules: Carbohydrates

(7)

Carbohydrate Stereochemistry

(1)

Monosaccharide Anomers

(3)

Disaccharides and Polysaccharides

(1)

Deoxy Sugars and Amino Sugars

(1)

Biomolecules: Amino Acids, Peptides, and Proteins

(9)

Amino Acids

(4)

Peptides and Proteins

(4)

Biomolecules: Nucleic Acids

(5)

DNA: Deoxyribonucleic Acid

(1)

RNA: Ribonucleic Acid

(1)

Biomolecules: Enzymes, Coenzymes, and Coupled Reactions

(16)

Enzymes

(3)

Coenzymes

(3)

Coupled Reactions and High-Energy Compounds

(3)

Problems

(7)

Lipid Metabolism

(68)

Digestion and Transport of Triacylglycerols

(8)

Triacylglycerol Hydrolysis

(2)

A Brief Note about Visualizing Enzyme Structures

(2)

Triacylglycerol Resynthesis

(3)

Triacylglycerol Catabolism: The Fate of Glycerol

102

(4)

Triacylglycerol Catabolism: Fatty-Acid Oxidation

106

(9)

Fatty-Acid Biosynthesis

115

(10)

Terpenoid Biosynthesis

125

(19)

The Mevalonate Pathway to Isopentenyl Diphosphate

126

(6)

The Deoxyxylulose Phosphate Pathway to Isopentenyl Diphosphate

132

(7)

Conversion of Isopentenyl Diphosphate to Terpenoids

139

(5)

Steroid Biosynthesis

144

(17)

Conversion of Farnesyl Diphosphate to Squalene

144

(4)

Conversion of Squalene to Lanosterol

148

(5)

References

153

(3)

Problems

156

(5)

Carbohydrate Metabolism

161

(60)

Digestion and Hydrolysis of Complex Carbohydrates

162

(2)

Glucose Catabolism: Glycolysis

164

(14)

Transformations of Pyruvate

178

(7)

Conversion of Pyruvate to Lactate

179

(1)

Conversion of Pyruvate to Ethanol

179

(2)

Conversion of Pyruvate to Acetyl CoA

181

(4)

The Citric Acid Cycle

185

(8)

Glucose Biosynthesis: Gluconeogenesis

193

(10)

The Pentose Phosphate Pathway

203

(8)

Photosynthesis: The Reductive Pentose Phosphate (Calvin) Cycle

211

(10)

References

216

(2)

Problems

218

(3)

Amino Acid Metabolism

221

(84)

Deamination of Amino Acids

223

(5)

Transamination of Amino Acids

223

(4)

Oxidative Deamination of Glutamate

227

(1)

The Urea Cycle

228

(4)

Catabolism of Amino Acid Carbon Chains

232

(39)

Alanine, Serine, Glycine, Cysteine, Threonine, and Tryptophan

234

(7)

A Brief Note about Oxidation States in Iron Complexes

241

(10)

A Brief Note about PLP Reactions

251

(1)

Asparagine and Aspartate

252

(1)

Glutamine, Glutamate, Arginine, Histidine, and Proline

252

(3)

Valine, Isoleucine, and Leucine

255

(4)

Methionine

259

(5)

Lysine

264

(1)

Phenylalanine and Tyrosine

265

(6)

Biosynthesis of Nonessential Amino Acids

271

(5)

Alanine, Aspartate, Glutamate, Asparagine, Glutamine, Arginine, and Proline

273

(1)

Serine, Cysteine, and Glycine

274

(2)

Biosynthesis of Essential Amino Acids

276

(29)

Lysine, Methionine, and Threonine

276

(8)

Isoleucine, Valine, and Leucine

284

(2)

Tryptophan, Phenylalanine, and Tyrosine

286

(9)

Histidine

295

(2)

References

297

(4)

Problems

301

(4)

Nucleotide Metabolism

305

(34)

Nucleotide Catabolism

307

(6)

Pyrimidines: Cytidine, Uridine, and Thymidine

307

(4)

Purines: Adenosine and Guanosine

311

(2)

Biosynthesis of Pyrimidine Ribonucleotides

313

(6)

Uridine Monophosphate

313

(5)

Cytidine Triphosphate

318

(1)

Biosynthesis of Purine Ribonucleotides

319

(8)

Inosine Monophosphate

319

(6)

Adenosine Monophosphate and Guanosine Monophosphate

325

(2)

Biosynthesis of Deoxyribonucleotides

327

(12)

Deoxyadenosine, Deoxyguanosine, Deoxycytidine, and Deoxyuridine Diphosphates

327

(2)

Thymidine Monophosphate

329

(3)

References

332

(2)

Problems

334

(5)

Biosynthesis of Some Natural Products

339

(70)

Biosynthesis of Penicillins and Cephalosporins

342

(10)

Penicillins

344

(5)

Cephalosporins

349

(3)

Biosynthesis of Morphine

352

(11)

Biosynthesis of Prostaglandins and Other Eicosanoids

363

(6)

Biosynthesis of Erythromycin

369

(10)

Biosynthesis of Coenzyme B12 and Other Tetrapyrroles

379

(30)

Uro'gen III

380

(4)

Heme

384

(3)

Coenzyme B12

387

(13)

References

400

(3)

Problems

403

(6)

A Summary of Biological Transformations

409

(20)

Hydrolyses, Esterifications, Thioesterifications, and Amidations

409

(2)

Carbonyl Condensations

411

(2)

Carboxylations and Decarboxylations

413

(3)

Aminations and Deaminations

416

(1)

1-Carbon Transfers

417

(2)

Rearrangements

419

(1)

Isomerizations and Epimerizations

420

(1)

Oxidations and Reductions of Carbonyl Compounds

421

(3)

Hydroxylations and Other Oxidations via Metal Complexes

424

(5)

Appendixes

429

(48)

A. Visualizing Protein Structures Using the Swiss PDB Viewer

429

(7)

B. Using the KEGG and BRENDA Databases

436

(5)

C. Answers to End-of-Chapter Problems

441

(33)

D. Abbreviations Used in This Book

474

(3)

Index

477

Amazon no longer offers textbook rentals. We do!

The Organic Chemistry Of Biological Pathways

The Organic Chemistry Of Biological Pathways

9780974707716

0974707716

Summary

Table of Contents

Supplemental Materials

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