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Multicomponent Reactions. Edited by Jieping Zhu and Hugues Bienyam

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Angewandte
Books
Chemie
Multicomponent Reactions
Edited by Jieping
Zhu and Hugues
Bienyam. WileyVCH, Weinheim
2005. 468 pp.,
hardcover
E 149.00.—ISBN
3-527-30806-7
Multicomponent reactions (MCRs)
have a long history that can be traced
back to the advent of the venerable
Strecker synthesis shortly after the
dawn of modern organic chemistry. A
number of other important multicomponent reactions, such as the Hantzsch
dihydropyridine synthesis, the Biginelli
reaction, and the Mannich reaction,
were also discovered in the early years.
In fairness, however, the recognition of
multicomponent reactions as a valuable
synthetic strategy should be attributed
to Ivar Ugi, who made seminal contributions to this area and provided a logical
framework for isocyanide-based multicomponent reactions. The recognition
by the pharmaceutical industry that
MCRs provided a unique and facile
entry into the synthesis of innumerable
organic compounds, especially peptides,
peptide mimetics, and heterocycles of
biological importance, has led to an
unprecedented level of activity in
MCRs during the last two decades.
Although a number of reviews on different classes of MCRs have been published in recent years, this is the first
book devoted to the subject, and it was
much anticipated.
The book has 13 chapters covering
some major classes of MCRs and related
Angew. Chem. Int. Ed. 2005, 44, 5769 – 5770
chemistry. The first chapter, which deals
with
asymmetric
isocyanide-based
MCRs (IMCRs), is a concise and introductory account of an area that is still
in its infancy. It is likely that this will
inspire organic chemists to explore
novel approaches to devise asymmetric
versions of the IMCRs. A useful account
of the elaboration of the products arising from the Passerini and Ugi reactions
is given in the second chapter. Consolidation of closely related reactions
using representative common schemes
would have made this chapter concise
and more appealing.
Chapter 3, which deals with new isocyanide-based MCRs, unfortunately
fails to cover much of the recent literature in this area. Significant and very
pertinent work by major contributors
such as Zhu (incidentally one of the editors), Yoshida, Yavari, and Nair is
almost totally ignored. This is surprising,
since the author is a leading exponent of
IMCRs. The many contributions from
the Nair group on novel MCRs involving zwitterions generated from isocyanides and acetylenic esters, and the
recent reports by Yoshida on aryne-isocyanide-based MCRs, are not discussed
even peripherally. Despite devoting
plenty of space to discussing Schreiber1s
work on U-MCRs, the author has not
cited the primary references to work
by Schreiber and other authors.
Chapter 4, on the Biginelli reaction,
is well-written, but to devote a separate
chapter to this reaction is not appropriate, considering the fact that more
important and versatile reactions attributed to Strecker, Hantzsch, and
Mannich have not found any significant place in this book. In this context,
one might also question the relevance
of Chapter 13 for inclusion in this
book. Although the accepted definition of MCRs would accommodate the
modified Sakurai reaction within its
scope, devoting the longest chapter of
the book (55 pp.) to this reaction is
not justified. That applies especially
to a book that has practically excluded many old and new bona fide
MCRs.
The treatment of the domino-Knoevenagel-hetero-Diels-Alder reactions in
Chapter 5 is excellent. The inclusion of
other varieties of domino reactions triggered by Knoevenagel condensation
would have rendered this chapter even
more useful. It is unfortunate that the
chapter
on
free-radical-mediated
MCRs has omitted some elegant work
in the area. Particularly conspicuous is
the neglect of contributions by Stork,
Pattenden, Zard, and others.
Organoboron-based MCRs are concisely presented in Chapter 7. In Chapter 8, which deals with metal-catalyzed
multicomponent reactions, the emphasis
is heavily on palladium-mediated reactions, ignoring important work involving
other metals. In particular, Vollhardt1s
work on cobalt-mediated reactions and
Barleunga1s work on MCRs involving
Fischer carbenes have not been given
adequate coverage. Chapter 9, on the
emerging area of organocatalysis, is topical, and the coverage is good. Chapter 10, which is concerned with an algorithm-based approach to MCRs, is an
excellent addition to the book, and
with the enormous progress made in
computational methods it is likely to
provide chemists with a new vision on
MCRs, and will enable them to invent
novel MCRs. Chapter 11, which deals
with applications of multicomponent
reactions in drug discovery, will be very
useful for medicinal chemists. However,
this chapter contains a lot of material
that can also be found elsewhere in the
book. The chapter on MCRs in the
total synthesis of natural products has
well-selected examples, and the presentation is good.
Although this is a timely book, it has
a number of problems, which unfortunately diminish its usefulness. Its most
serious shortcoming is the omission of
some important contributions to the
field,
including—surprisingly—the
work of one of the editors. The subject
index is inadequate, and there is no
author index. In many chapters, the
schemes are separated from the discussion and the corresponding text by several pages. A more active editorial
input, better coordination between the
chapter authors, a more judicious
choice of topics, and the inclusion of a
chapter giving a general introduction
to MCRs, would all have added
immense value to this book. Hopefully,
these issues will be addressed in the
next edition of the book. Notwithstanding the above criticism, as this is the first
book of its kind it will be useful to the
) 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5769
Books
specialists in the field. Naturally, libraries may also like to acquire this book.
Vijay Nair
Regional Research Laboratory
Council of Scientific and Industrial
Research (CSIR)
Trivandrum (India)
DOI: 10.1002/anie.200585290
Protein Microarray Technology
Edited by Dev
Kambhampati.
Wiley-Interscience,
New York 2004.
243 pp., hardcover
E 99.00.—ISBN
3-527-30597-1
Protein microarray technology has
recently emerged as a promising tool in
proteomics, drug discovery, and clinical
diagnostics. Despite its unrivaled combination of miniaturization, sample efficiency, and parallelization, progress in
this field up to now has depended on a
very small number of research groups.
Presumably, access to the benefits of
this technology has been limited not
only by the cost and effort of providing
the necessary instrumentation, but also
by the lack of descriptive literature.
Thus, the book Protein Microarray Technology, as the first of its kind, will help
interested researchers to enter this
fast-growing area.
The text is organized in 10 chapters,
which are devoted to the main aspects of
successful application of protein microarrays: surface chemistry, microarray
production, detection techniques in the
context of the envisioned application,
and data analysis.
After an outline of the current state
of the art in the field, as well as existing
applications and challenges (Chapter 1),
Chapters 2 and 3 provide a comprehensive summary of the surface chemistry
techniques that are currently available
5770
www.angewandte.org
for microarray production. The discussion also covers some techniques that
are rarely applied, but have great potential, such as photochemical crosslinking
and the use of tagged proteins. Chapters 4–7 and 9 describe various labelfree detection techniques, with the
main focus on methods based on the surface plasmon effect. Described are analysis of surface plasmon resonance
(SPR), based on Biacore1s well-established optical angle shift measurements
(Chapter 4), its extension to spatially
resolved monitoring of binding to biomolecules by SPR imaging on gold surfaces (Chapter 5), and the related technique of surface plasmon fluorescence
spectroscopy (SPFS), which can achieve
remarkably low detection limits, as
exemplified here by protein binding
studies (Chapter 6).
Chapter 7 describes the combination
of protein microarrays with surfaceenhanced laser desorption ionization
mass
spectrometry
(SELDI-MS),
whereas Chapter 9 exemplifies the combination with nanomechanical cantilever
sensors. The two chapters provide valuable information about these new detection techniques, and underline the fact
that there is a broad spectrum of possible
applications of protein microarrays.
SELDI-MS, for example, has been
applied to the parallel detection of multiple kinase activities in crude cell extracts,
whereas nanomechanical cantilever
arrays can transform many different
types of biochemical interactions into signals, for example, by utilizing the tiny
temperature changes that result from
chemical reactions, or by measuring the
change in weight upon a binding event.
Chapter 8 provides detailed information about the production of protein
microarrays, and includes comprehensive lists of commercially available
slide surfaces and companies developing
and offering proteins in microarray formats. Finally, Chapter 10 discusses the
analysis of fluorescent high-density
arrays, and gives a clear description of
the software parameters to be set, and
the potential pitfalls. Examples are
described to show how the choice of
software settings can significantly
affect the results.
) 2005 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
The strength of this book is its broad
coverage of the topic. It provides information about all relevant aspects of protein microarrays, and is therefore a valuable reference source about various
developments in the field, especially as
it gives good coverage of the primary literature up to 2003. The chapters on surface chemistry, printing procedures, and
the analysis of fluorescence data are
especially good, and will help newcomers to apply this technology with success.
The chapters on alternative read-out
technologies provide an up-to date reference source about these emerging
methods.
The main weakness of the book is
that the discussion of detection methods
for protein microarrays does not accurately reflect the emphasis of current
research trends. The widely used
method of fluorescence detection is
only treated in connection with data
analysis, whereas the five chapters
about label-free detection methods
give an unduly strong emphasis to
these alternative read-out techniques.
In particular, a chapter of 49 pages on
established Biacore applications, which
has only slight relevance to microarray
read-out, is definitely excessive. Further
points of criticism are concerned with
technical matters of presentation, such
as the poor quality of some of the figures, and several cases where special
characters are missing.
Overall, this text fills a gap in the literature. By presenting the combined
knowledge of 24 leading experts, it certainly lowers the activation barrier that
the novice has to overcome to enter
the field. It also provides a good source
for new ideas upon careful reading.
Therefore, I can recommend the book
for students and researchers planning
to use protein microarrays, and to specialists seeking new methods of detection.
J"rg Eppinger
Fakult;t f<r Chemie
Technische Universit;t M<nchen
Garching (Germany)
Angew. Chem. Int. Ed. 2005, 44, 5769 – 5770
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