Book Review

Book cover image

Chemistry of Peptide Synthesis

N. L. Benoiton
CRC Press, 2006, 290 pages

This useful but expensive CRC Press book describes the chemical reactions for chemically synthesizing peptides, a topic that is constantly changing due to the enormous economic incentives in industry for improving efficiency and purity. Although it is now possible to buy custom peptides at a reasonable price, peptide vendors are frequently unable to synthesize anything other than simple linear peptides. This means that chemists must occasionally still know how to make peptides on their own. The reactions themselves are extraordinarily efficient; unlike the usual 70-80% yields in ordinary organic chemistry, reactions used for peptide synthesis are often over 99% efficient. This makes them useful for many other applications besides making peptides. However, there are very few up-to-date books that describe these reactions.

Chemistry of Peptide Synthesis is a bona fide textbook, not a collection of articles by different authors. It is clear that much effort has been expended in making the writing style as clear as possible. In fact, the author seems to have written the book as much from strongly-held, almost curmudgeonly opinions about peptide nomenclature as from an interest in the topic itself. For example, as the back cover says, the book "employs only the precise terms of enantiomerization and epimerization." The author emphasizes in no uncertain terms that these two words are quite distinct in meaning. Furthermore, the protecting group Boc, says the author, should never be referred to as "t-Boc", because the 't' is implied by the chemical structure.

However, the utility of the book is greatly diminished by two major problems. The first problem is the figures. Although the diagrams are readable, or at least decipherable, with some effort, the molecules are all packed together confusingly. Chemical structures are drawn in an unconventional and bulky way. Arrows sometimes indicate the flow of electrons, and sometimes indicate the reaction pathway. Other times, arrows travel long distances to reach other molecules hiding coyly on the other side of the diagram. Arrows appear to come from or go to nowhere, point to other arrows or to chemically unrelated and impossible products, or travel from the name of the molecule to the molecule itself, while other molecules sit lonely by themselves, with no arrows at all (see example below).

The other problem is that the index is organized into grand topics like "Reagents" and "Names of scientists", in a manner reminiscent of the old Allied Electronics Catalog, rendering the index almost useless and making things very difficult to find. Other than that, the book is very useful. Alternative methods and reagents are described, along with their benefits and liabilities, and mechanisms are explained in detail. The references (mostly to classic papers) are conveniently included at the end of each section in each chapter. Unlike Solid Phase Peptide Synthesis: a Practical Approach by Atherton and Sheppard, no specific procedures are described; the reader must consult the primary literature to learn the reaction conditions. However, Solid Phase Peptide Synthesis is now out of print. Fmoc Solid Phase Peptide Synthesis: A Practical Approach by Chan and White is by far the best book on the topic, providing a clear exposition, with readable diagrams, detailed protocols, and is up to date, making it an ideal choice for those interested in knowing the standard way of making peptides today. Unlike many other books, Fmoc Solid Phase Peptide Synthesis also covers topics like branched peptides.
peptide synthesis scheme

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November 28, 2005 Back