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Book Review Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook. Volumes 1 and 2. Edited by K. Drauz and H. Waldmann

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Enzyme Catalysis in Organic Synthesis. A Comprehensive Handbook. Volumes 1 and 2. Edited by K. Druiii and
H . Wrrldmmt~.VCH Verlagsgesellschaft. Weinheim, 1995. 1050 pp.,
hardcover DM 498.00, $475.00.ISBN 3-527-18479-6
Enzyme-catalyzed reactions are now an
important part of the armory of modern
organic synthesis. These reactions proceed under mild conditions. with high
substrate specificity and with high stereo-.
regio-. and chemoselectivity. The main
area of application of enzymatic reactions
is in the synthesis ofenantiomerically pure
and polyfunctional compounds. Because
of the enormous developments that have
occurred in this area during the past
decade. it seemed an appropriate time to
bring together the current state of knowledge III the form of this substantial multiauthor work. The articles in this handbook have been written by 53 recognized
international experts. They cover the literature up to the beginning of 1994, with
over 4000 references. and the subject index of more than 70 pages serves as a very
effective key to the contents.
The work is divided into three parts.
The first. consisting of about 160 pages,
contains an inlroduction followed by
chapters on the production and isolation
of enzymes. their immobilization. process
engineering for enzyme-catalyzed biotransformations. and microbiological
transformations using growing and resting cells. This part of the book introduces
the basic principles of enzyme-catalyzed
reactions, including enzyme kinetics and
the standard techniques for preparing. purifying m d using enzymes.
The second part (about 800 pages) begins with eight chapters that are essential11 devoted to different types of enzyme-
catalyzed reactions that can be used in
synthesis. These are followed by four
shorter chapters dealing with special applications of enzymes. The first chapter
(about 200 pages) covers the hydrolysis
and formation of CO bonds. This includes
esterase- and lipase-catalyzed kinetic
raceinate separation processes based on
the hydrolysis of carboxylic acids and the
esterification of alcohols. Asymmetrization reactions of mesn and prostereogenic
carboxylic acid derivatives and alcohols
are also treated in detail. This chapter also
deals with the hydrolysis of epoxides by
epoxide-hydrolases and the use of glycosidases and glycosyl-transferases for forming and breaking glycosidic bonds. The
following chapter (240 pages) is concerned with the formation and hydrolysis
of CN bonds including. for example. the
hydrolysis of nitriles using nitrilases. and
the use of nitrile-hydratase to catalyze
amide formation followed by the
protease-catalyzed hydrolysis of the
amides. The use of proteases for the hydrolysis and formation of peptide bonds is
treated i n detail, and considerable space is
devoted to the synthesis of amino acids
and peptides using proteases. Next is a
chapter of 40 pages on the formation and
breaking of PO bonds. This i s followed by
a chapter of about SO pages on the formation of CC bonds using aldolases. transketolases, or transaldolases. or by addition
of hydrogen cyanide to aldehydes and ketones using oxynitrilases. The following
chapter (about 70 pages) deals with the
application of dehydrogenases to the reduction of aldehydes. ketones, carboxylic
acids. C=N bonds, and C=C bonds. A
chapter of over 130 pages is devoted to a
survey of oxidation reactions. including
hydroxylations. epoxidations, cis-dihydroxylations of arenes, oxidations of alcohols, Baeyer-Villiger oxidations. oxida-
tions of sulfides, and halogenations, using
mono- and dioxygenases. oxidoreductases. and peroxidases. A 40-page chapter
then covers enzyme-catalyzed isomerizations such as the racemization of amino
acids by racemases. Next is a chapter discussing numerous examples where enzyme-catalyzed reactions have played a
valuable role in the use of protecting
groups. These methods achieve selective
protection of amino, thiol. carboxyl, and
hydroxyl groups, mainly in polyfunctiona1 molecules. The next chapter reviews the
use of catalytic antibodies in organic synthesis. This second part ends with three
shorter chapters on enzymatic analysis
and biosensors, protein engineering, and
enzymes derived from highly thermophilic
and hyperthermophilic archaeabacteria
and eubacteria. The third part contains
tables giving information about commercially available enzymes and suppliers.
This handbook i s an indispensable
source of information about all types of
enzyme-catalyzed reactions that can be
used in syntheses. The many examples of
the use ofenzymes in organic synthesis are
in themselves enough to make this twovolume work an enormously valuable resource. The wealth of information is presented in a very clear form; in particular
the presentation of results in tables enables the reader to quickly find the essential data, and also provides stimulating
ideas for following up. The work is intended for synthetic chemists in academic
and industrial research. and for biochemists. microbiologists. and biotechnologists whose work involves biotransformations. It i s very clearly set out, easy
to read, and sturdily bound. It should be
in every library.
Fritz Tlicil
Institut fur Angewandte Chemie
Berlin-Adlershof (Germany)
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