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Reagents for Glycoside Nucleotide and Peptide Synthesis. Handbook of Reagents for Organic Synthesis

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Silverman discusses solvent hydrogen isotope effects in reactions catalyzed by
carbonic anhydrase. The transfer of
hydrogen atoms in enzymatic reactions
is addressed in the chapter by HammesSchiffers on proton-coupled electron
transfer, while Kohen uses kinetic isotope
effects as a probe to study hydrogen
tunneling in enzymes. The mechanism of
CH bond cleavage by enzymes such as
coenzyme B12 or lipoxygenase is discussed
by Siebrand and Smedarchina, while
Klinman describes enzymatic oxygen
(18O) activation, and Schramm discusses
isotope effects on enzymatic binding.
The book can be recommended as a
reference source for people working in
the field of isotope effects, as well as a
textbook for advanced students who
want to deepen their understanding of
the usefulness of isotope effects.
Thomas Strassner
Physikalische-Organische Chemie
Technische Universitt Dresden
Reagents for Glycoside,
Nucleotide, and Peptide Synthesis
Handbook of
Reagents for
Organic Synthesis.
Edited by David
Crich. John Wiley &
Sons, Hoboken
2005. 786 pp.,
E 125.00.—ISBN
The book Reagents for Glycoside,
Nucleotide and Peptide Synthesis,
edited by David Crich, is, of course, a
handbook, as is clear from the series
title Handbook of Reagents for Organic
Synthesis. However, is it not also much
more than that? More about that later.
As is stated in the introduction,
although a third of the factual information about the reagents and their applications in this book has been taken from
the Encyclopedia of Reagents for
Angew. Chem. Int. Ed. 2006, 45, 6420 – 6421
Organic Synthesis (EROS), which was
published in 1995, the greater part of it
comes from publications that have
appeared in the last ten years. Thus,
the book gives the reader an up-to-date
survey of the recent literature on
reagents that are important for the
synthesis of glycosides, nucleosides, and
The descriptions of how the reagents
are used are presented in separate short
chapters, which together achieve a successful blending of minireview and textbook. In accordance with this textbook
character, in many cases the chapters
explain the reaction mechanisms or the
details of how the reagents work, while
they also indicate their range of applications and their limitations. The way in
which the chapters on individual
reagents are structured in this book
reminds one of Organisch-Chemische
Experimentierkunst, edited by G. Hilgetag, but unlike that work it does not
subdivide the reagents into separate
groups for the synthesis of glycosides,
nucleosides, and peptides. It was a clever
decision to treat the reagents in alphabetical order, as it avoided the need for
many repetitions and cross-references to
other chapters. Otherwise they would
certainly have been necessary, because
in many cases the same protecting group
techniques and linking methods are
used in the synthesis of all three classes
of biomolecules. This way of combining
the descriptions within and across the
different classes of biomolecules, for
example when describing the synthesis
of fragments that are common to glycopeptides and peptidoglycans, also means
that it is no longer even possible to
group the reagents according to the
synthetic requirements within individual
classes of biomolecules.
The book is addictive! From the
moment when the reader, as an enthusiastic natural products chemist, first
opens the book, it is almost impossible
to stop turning the pages or becoming
absorbed in reading one or another of
the chapters. At least, that is how it
affected this reviewer, on first picking
up the book at the Wiley stand during an
interval at a symposium.
Part of the book5s fascination is that
there are so many different ways of
using it. Firstly, it is a valuable reference
source for students working for their
degree at graduate, master, or doctorate
level. To illustrate that, let us take the
example of 1,3-dicyclohexylcarbodiimide. Under this heading the up-andcoming scientist can find physical data
about the reagent, and information
about its solubility, storage requirements, handling, and additional safety
precautions. He or she will also find
practical advice about the use of the
compound, in the form of a short
laboratory protocol. That is followed
by information about the main applications of the reagent, with the relevant
literature references. All this information about dicyclohexylcarbodiimide is
collected together within three pages.
Secondly, a chemist can use the
handbook to build up an index of
methods. However, for this purpose it
would be desirable to have the reagents
also grouped according to areas of
application, such as oxidation, reduction, glycosylation, carboxyl group activation, etc.
The usefulness of the book would be
further increased if a future edition
could be provided with such an enlarged
subject index, which would require an
amount of work that seems manageable.
In that way the handbook could also be
used as the basis for a set of lecture
notes on the broad subject: “modern
aspects of the synthesis of oligosaccharides, oligopeptides, and oligonucleotides”. If that were done, in view of the
wealth of available material there would
be a wide range of possibilities regarding
the choice of main topics and the title of
the teaching package. The emphasis
might be on methods, on mechanisms,
or on purely synthetic aspects. Such
teaching packages based on this book
would be especially valuable because of
the many up-to-date literature references.
In summary, this handbook provides
a wealth of up-to-date, well arranged,
and helpfully structured material, which
can be used in many different ways. It is
a must for every natural products chemist working on synthetic aspects.
Christian Vogel
Institut f8r Chemie
Abteilung Organische Chemie
Universitt Rostock (Germany)
DOI: 10.1002/anie.200585426
; 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
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synthesis, reagents, nucleotide, organiz, glycosides, handbook, peptide
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