Biochemistry: An Organic Chemistry Approach

Book Preface

The focus of this book is to use organic chemistry principles and reactions to explain the fundamentals of biochemistry. The inspiration for this book came from teaching the second semester of  organic chemistry with many students who were taking introductory biochemistry at the same time.
Many students commented that the things we were discussing in organic chemistry helped explain  and better understand the concepts they were discussing or had discussed in biochemistry. On many  occasions, topics were discussed in organic chemistry that had been covered previously in the biochemistry course. An understanding of the organic chemistry reactions and mechanisms helped the  students better understand many of those biochemical principles. It is hoped that understanding the  organic chemistry foundations of biochemistry will provide similar assistance to students today.
Where feasible, organic chemical reactions such as those found in a typical undergraduate organic  chemistry course are included in this book to bring their biological chemistry counterparts into  perspective.

The frst chapter is meant as a review of the fundamentals of an undergraduate organic chemistry course. For those who have not had a full organic chemistry course, this chapter will not suffce. This chapter is only intended as a supplement for an organic chemistry course and to  function as a review for the biochemical principles to follow. The next chapter discusses the  importance of water in chemistry and also acid-base chemistry Elimination reactions such as  E2 and E1 reactions are introduced here as well. The third chapter discusses nucleophilic substitution and chapter Chapter 4 discusses radicals and radical reactions. Dienes and conjugated  systems are discussed in Chapter 5, along with sigmatropic rearrangements. Enols and enolate  reactions are discussed in the next chapter, including aldol-type reactions and Claisen condensation type reactions.
Chapter 7 introduces enzymes, enzyme kinetics and classes of enzymes. Pertinent organic chemical reactions are included for each enzyme class for a direct comparison. Chapter 8 discusses  carboxylic acids and acid derivatives as well as various lipids. Chapter 9 is devoted to aromatic  chemistry, including the SEAr and SEAr reactions. Heterocyclic aromatic compounds are also discussed in this chapter.
Chapter 10 introduces organometallic compounds, beginning with the well-known Grignard  reagents and organolithium reagents. Biologically relevant metals and chelating reagents are discussed in this chapter. Amino acids are introduced in Chapter 11 and the use of amino acids to form  peptides and proteins, as well as the importance of those biologically important compounds are  discussed in Chapter 12. Carbohydrates are introduced in Chapter 13. The chemistry of carbohy drate derivatives and glycosides is elaborated in Chapter 14. Chapter 15 concludes the book with a  discussion of nucleosides, nucleotides, DNA and RNA.

I thank all of my former students who inspired this book with the sincere hope that this approach  will help those students interested in biochemistry. I also thank editors Hilary Lafoe and Jessica  Poile and my publisher, Dr. Fiona McDonald, and all at Taylor & Francis, for their support and their  help. This book would not have been possible without them.

All structures and reactions were drawn using ChemDraw Professional 18.0.0.231. I thank  PerkinElmer Informatics, Inc. for a gift of this software. All 3-D drawings and molecular models  were prepared using Spartan’18 software, version 1.2.0 (181121). I thank Warren Hehre and Sean  Ohlinger of Wavefunction, Inc. for a gift of this software. I thank Ms. Christine Elder (https://christineelder.com), graphics design artist, for her graphic arts expertise to render the drawings in Figures  1.4, 1.9, 1.11, 1.15, 1.16, 1.20, 1.22, 1.29, 1.32, 1.37, 1.44, 1.45, 2.7, and 9.1.

Every effect has been made to keep this manuscript free of errors. Where there are errors, however, I take full responsibility and encourage readers to contact me at the email provided with questions, comments and corrections. Thank you.
Michael B. Smith
Professor Emeritus
University of Connecticut