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Carbohydrate-Based Drug Discovery. 2 Volumes. Edited by Chi-Huey Wong

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Reactive Intermediate Chemistry
Edited by Robert A.
Moss, Matthew S.
Platz and Maitland
Jones, Jr.. WileyInterscience, New
York 2003.
1042 pp., hardcover E 97.90.—
ISBN 0-471-23324-2
The chemistry of reactive intermediates—is this not a mature area of
research that has long since been
worked out? Certainly not! New evidence of that is provided by the monograph Reactive Intermediate Chemistry.
As editors for the book, the publishers
have obtained the services of three
widely recognized experts in the field:
Robert Moss, Matthew Platz, and Maitland Jones, and the list of contributing
authors is equally impressive. The book
is divided into two main parts. The first
(larger) part is devoted to describing
the chemistry of reactive intermediates.
The reader learns about the entire
range and the many types of reactive
molecules as intermediates, starting
from carbocations and free radicals,
and continuing through carbenes to
strained hydrocarbons and arynes. The
second, more compact, part is concerned with advanced experimental
techniques of modern physical-organic
chemistry and concentrates on matrix
isolation methods and time-resolved
laser spectroscopy with nanosecond,
picosecond, or femtosecond resolution.
These chapters have almost the character of instructions for using these techniques. The last two chapters of the book
Angew. Chem. Int. Ed. 2004, 43, 3995 – 3996
are concerned with theory and with the
fruitful interaction between theory and
experiment. In particular, the final chapter by W. T. Borden on “The Partnership
between Electronic Structure Calculations and Experiments in the Study of
Reactive Intermediates” contains much
advice about which methods of calculation are most useful for which types of
reactive intermediates, which is very
helpful in view of the unusual “electronic structures” of many reactive molecules.
Returning now to the first part of the
book, the contents of this part can be
roughly divided into two categories. Several of the chapters are typical review
articles, summarizing the recent literature in particular areas of research,
such as work on silylenes and on stannylenes. Other chapters, such as those on
carbocations (R. A. McClelland) and
on non-Kekul4 molecules (J. A.
Berson) are almost of textbook character! The fact that these chapters certainly do not neglect the most recent
research results is an indication of the
high didactic quality of most of the
authors in this book.
Of course, the book is not completely free of errors. However, I was
able to find only one error that significantly affected the information given:
the energy difference between the triplet ground state and the first excited singlet state in phenylnitrene is not
11 kcal mol 1, as given in Figure 13.31,
but 18.5 kcal mol 1, and therefore the
conclusion drawn from this Figure is
In summary, this is a very nice book,
which is an absolute must for every
chemist concerned with reactive intermediates. It could also be useful to synthetic chemists as a mine of information,
and furthermore several of the chapters
(such as that by M. P. Doyle on metallocarbenes and metallonitrenes) are of
special interest to this group of readers.
The book can also be recommended to
advanced students in view of the didactic quality of many of the chapters.
Gtz Bucher
Lehrstuhl f(r Organische Chemie II
Universit.t Bochum (Germany)
Carbohydrate-Based Drug
2 Volumes. Edited
by Chi-Huey Wong.
Wiley-VCH, Weinheim 2003. 2 Vol,
xxxii + 948 pp.,
E 349.00.—ISBN
The fields of glycochemistry and glycobiology have undergone rapid development in the last few years. Thus, the
Investigational Drugs Database now
contains 145 entries for agents containing carbohydrates, of which 14 are products already on the market. These developments are covered in the two-volume
work, edited by Chi-Huey Wong, that is
reviewed here. In 35 chapters, a team of
more than 80 authors, drawn from universities, private research institutions,
and industry, presents a comprehensive
picture of carbohydrates research, with
special emphasis on biological aspects
and therapeutic applications.
The first part of Volume 1 is devoted
to synthesis. Introductions to the
chemistry of glycosylation and sialylation are followed by discussions of
solid-phase and enzymatic methods of
synthesis. Subsequent chapters discuss
the synthesis of glycopeptides and complex natural products, a chapter on glycosylation of proteins, and other topics.
The first pharmacologically orientated
sections are concerned with lipid A
(sepsis) and with vaccines, which are discussed in great detail in several chapters.
The next two chapters, dealing with heparins, are also well-worth reading. The
first of these is concerned with the pharmaceutical potential of heparins. The
second is a case study describing the
research path that led to the development of a synthetic heparin. The 55stage synthesis of this pentasaccharide,
which is now being marketed commercially, is an interesting example of the
opportunities of purely synthetic carbohydrates.
Volume 2 deals with a wide variety
of topics, such as sulfotransferase inhibitors, anti-influenza drugs, glycolipid
9 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
mimetics, and interactions between
RNA and aminoglycosides (antibiotics),
to mention just a few examples. There is
also a detailed discussion of glycosyl
transferase inhibitors.
The variety of topics covered is completed by a group of chapters devoted to
techniques. One of these is concerned
with the conformational analysis of Cand O-glycosides. Modern methods of
structural elucidation by mass spectrometry and NMR spectroscopy are also
described. There is a detailed discussion
of the phenomenon of multivalence,
which is a key factor in the recognition
of antigens by cells. Unfortunately, the
important topic of carbohydrate arrays,
which would have deserved to be
treated in a separate chapter, is somewhat hidden within chapters on other
It would have been desirable to provide an introductory chapter presenting
an overview of the many areas in
which carbohydrates have an important
role, to ease the way for a reader with
no previous knowledge of the field. A
summary of carbohydrate-containing
drugs that are already on the market or
at an advanced stage of development
would also have made interesting reading. Although Chapter 25 provides an
overview of the variety of structures
and biological activities of natural products containing glycosyl groups, and
many of the chapters contain discussions
of commercial products, the reader
needs to put in considerable effort to
obtain a broad overview of drugs in
development from this book.
However, despite these minor shortcomings, this is a very useful work of
high quality. Every chapter begins with
a general introduction to the topic,
then gives a detailed survey of the present state of development. Each chapter
also includes many recent literature references, thus making it easy for the
reader to study topics in more depth
and to explore areas beyond the scope
of the chapter. One of the workBs
strengths is that some topics are
returned to again in later chapters, so
that one benefits from discussions that
emphasize different aspects. This
makes it easier to recognize connections, and avoids overloading individual
chapters. A few special topics that are
certainly important in carbohydrate
research, such as inositols or cyclodextrins, receive relatively little attention
in these volumes, but nevertheless the
work gives a broad coverage of the
vast majority of the aspects that are currently of interest.
9 2004 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Regrettably, the chemistry and biology of carbohydrates is often still
regarded as primarily an academic discipline. The compounds in this area are
often rated as lacking druglike characteristics and therefore of little interest.
After studying this work, a different
view will be opened up to the reader.
It contains clear descriptions and discussions of the synthesis of carbohydrates
and of the biological processes in
which these compounds have an important or even a crucial role, and covers
pharmaceutical applications and trends
for future developments.
To summarize, the work provides a
comprehensive and excellent survey of
the present situation in carbohydrate
research, in which many interesting
details can be spotted. Because of the
wide range of topics covered, the
reader will refer to it again and again.
It is likely to become a standard work
on the subject, not exclusively for carbohydrate chemistry enthusiasts.
Oliver Plettenburg, Ulrich Stilz
Medizinische Chemie
Aventis Pharma Deutschland
Frankfurt am Main (Germany)
DOI: 10.1002/anie.200385089
Angew. Chem. Int. Ed. 2004, 43, 3995 – 3996
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base, discovery, volume, chi, drug, huey, wong, edited, carbohydrate
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