Book Review

Biotransformations in Organic Chemistry, 5th edition

K. Faber
Springer, 2004, 454 pages

Enzymes in Synthetic Organic Chemistry
(Tetrahedron Organic Chemistry Series Vol. 12)

C. H. Wong and G. M. Whiteside
Pergamon, 1994, 370 pages



The use of enzymes in organic synthesis has produced some spectacular successes. For example, Rhodococcus bacteria can transform acrylonitrile to acrylamide in yields over 99% with no risk of polymerization or over-oxidation to acrylic acid. This is used commercially at a scale of 30,000 tons per year. Proteases have found wide usage in laundry detergents. Enzymes have the advantage that they are enantioselective, easy to separate from the product, are highly specific, and not least, are less likely to frighten consumers who have been conditioned by the media to fear synthetic chemicals. However, because of the specificity of enzymes, and the real and imaginary limitations of enzymes, most organic chemists use enzymes only as a last resort. Many chemists are also unfamiliar with the vast number of enzymes that are available, their reactions and cofactor requirements, and the potential side-reactions and problems that can occur with enzymes. These two books aim to introduce enzymes to organic chemists with the hope of changing this situation.

Both books are written in textbook style. Each book has its own strengths and weaknesses. For example, Enzymes is definitely not a beautifully-typeset book. On the other hand, the printing in Biotransformations, while nicer, is light and difficult to read. More importantly, both books omit major classes of reactions that could potentially be of immense value to chemists. Here is my biased, incomplete, and subjective summary of some of the reactions that I could find in each book:
Reaction Biotrans­formations Enzymes               
Synthesis of amides √ (not in index)
Formation of hydroperoxides by oxygenases in passing
Reactions of sterols / steroids in passing
Cholesterol synthesis from squalene no
Transaminases in passing
Transglutaminases no no
Halogenation no
Hydrolysis of nitriles
Synthesis of epoxides √ (not in index)
Hydrolysis of epoxides brief mention
Enantioselective reduction of ketones
Phosphorylation of alcohols by kinases
Microbial Baeyer-Villiger reactions
Aldol condensation (formation of C-C bonds)
Number of references in chapter on hydrolysis 684 361

From this table, Biotransformations would appear to have a strong edge in most categories. Part of the difference lies in the much better index in Biotransformations. For example, in Enzymes, addition of O2 to lipids to form hydroperoxides is only indexed under "lipoxygenase" and not under "double bonds", "oxygen", or "hydroperoxides", while all of these are listed in Biotransformations. Biotransformations is also more complete, with better coverage and more references in most chapters. However, Enzymes seems to be better at covering the difficulties and drawbacks of the reactions. Enzymes also has more Larock-style tables showing examples of reactions. For my purposes, which was to learn how to use enzymes to form unusual amide bonds in a peptide, both books, as the kids say, totally sucked.

Enzymes are particularly good at catalyzing hydrolytic reactions. Unfortunately, as with any catalyst, the reaction runs in both directions, and the ratio of substrate to product is determined by their relative thermodynamic stability. Thus, the idea of using a protease in reverse to synthesize peptides as both books suggest, is not likely to win many converts. Nevertheless, for the growing class of pharmaceutical biomolecules, enzyme-catalyzed reactions are a useful tool that organic chemists should become more familiar with.

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November 23, 2005 Back