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The Organic Chemistry of Biological Pathways

Second Edition ©2016 John E. McMurry; Tadhg P. Begley

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The Organic Chemistry of Biological Pathways was written for an audience of advanced undergraduates and graduate students who want a deeper understanding of the chemical reactions that take place in living organisms. The authors assume readers have a background in organic chemistry at the level of the typical two-semester college course. Although enzymes are crucial to biological reactions, the authors’ focus always remains on the reactivity patterns of the substrate molecules and on the organic, arrow-pushing details of the individual reactions.

The authors begin the book with a brief review chapter on the fundamental organic reaction mechanisms commonly found in biochemical pathways. Following this brush up on reaction mechanisms is a general introduction to the main classes of biomolecules. Then comes the heart of the book: full chapters devoted to the major metabolic pathways of the main classes of biomolecules—lipids, carbohydrates, proteins, nucleotides, and secondary metabolites. In the course of these chapters, readers cover the chemistry of the common coenzymes, see examples of the common sorts of biological transformations, and ultimately begin to develop an understanding of the patterns found throughout bioorganic chemistry. The authors conclude with a summary of the reaction patterns and mechanisms frequently used in nature to effect chemical transformations, followed by a brief chapter summarizing some general themes of enzymatic catalysis.

All mechanisms have been updated in this second edition, and several hundred references to recent literature are given for those students who want more detail.

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New to This Edition

"The book's greatest strength is its emphasis on the conceptual unity of organic chemistry and biochemistry. The chemical structures are presented with great care and accompanied by lucid explanations." —Charles Clapp, Bucknell University
"This textbook elegantly portrays the complementary nature of chemistry and biology. By describing biological processes in detailed chemical terms, the authors have provided a resource that provides an unparalleled look into the fascinating and emerging field of chemical biology." —Hung-wen Liu, University of Texas
"This textbook satisfies a major need in chemistry curricula, bridging the gap between introductory organic chemistry and biochemistry/biology. It is the first book written for students that presents biological transformations from the perspective of organic mechanism. The book significantly augments modern biochemistry curricula and may catalyze a resurgence of interest in biological mechanism." —Carolyn R. Bertozzi, University of California, Berkeley
"This text provides a contemporary and authoritative treatment of the molecular logic of the chemistry of life." —Christopher T. Walsh, Harvard University
"This text/reference book uniquely bridges organic chemistry and biochemistry and appears at an opportune time when an understanding of chemical biology is becoming essential. It should be indispensable for all bioscientists interested in a chemistry-based clarification of biological pathways." —Koji Nakanishi, Columbia University
"McMurry and Begley present the logic of biosynthetic pathways in the language of organic chemistry. This text will serve as an essential guide for new students of biological chemistry and will also prove a resource for the experienced student who aims to understand the molecular basis of biological chemistry." —Milan Mrksich, Northwestern University

The Organic Chemistry of Biological Pathways

John E. McMurry; Tadhg P. Begley

The Organic Chemistry of Biological Pathways

Second Edition 2016

John E. McMurry; Tadhg P. Begley

1. Organic Mechanisms in Biological Chemistry

2. Biomolecules and Their Chirality

3. Lipids and Their Metabolism

5. Amino Acid Metabolism

6. Nucleotide Metabolism

7. Biosynthesis of Some Natural Products

8. A Summary of Biological Transformations

9. Chemical Principles of Enzymatic Catalysis

Appendixes

A. Visualizing Protein Structures Using PyMOL

B. Using the KEGG and BRENDA Databases

C. Answers to End-of-Chapter Problems

D. Abbreviations Used in this Book

Index

The Organic Chemistry of Biological Pathways

Second Edition 2016

John E. McMurry; Tadhg P. Begley

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John E. McMurry

John E. McMurry received his B.A. from Harvard University and his Ph.D. at Columbia University. Dr. McMurry is a Fellow of the American Association for the Advancement of Science, and an Alfred P. Sloan Research Foundation Fellow. He has received several awards, which include the National Institutes of Health Career Development Award, the Alexander von Humboldt Senior Scientist Award, and the Max Planck Research Award. In addition to The Organic Chemistry of Biological Pathways, he is also the author of Organic Chemistry, Fundamentals of Organic Chemistry, and Chemistry (with Robert Fay).

Tadhg P. Begley

Tadhg P. Begley received his B.Sc. from National University of Ireland and his Ph.D. at the California Institute of Technology. Dr. Begley is the recipient of many awards, including the Merck Faculty Development Award and the Camille and Henry Dreyfus Teacher-Scholar Award. His research group uses the principles and techniques of organic chemistry to study complex organic transformations found in vitamin biosynthetic pathways. In addition to The Organic Chemistry of Biological Pathways, Dr. Begley has edited Cofactor Biosynthesis: A Mechanistic Perspective.

The Organic Chemistry of Biological Pathways

Second Edition 2016

John E. McMurry; Tadhg P. Begley

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The Organic Chemistry of Biological Pathways

Second Edition ©2016 John E. McMurry; Tadhg P. Begley

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Table of Contents

Authors

John E. McMurry

Tadhg P. Begley

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Equations

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The Organic Chemistry of Biological Pathways

Second Edition| ©2016 John E. McMurry; Tadhg P. Begley

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Authors

John E. McMurry

Tadhg P. Begley

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Second Edition ©2016 John E. McMurry; Tadhg P. Begley