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Chemistry of Peptide Synthesis. Edited by N. Leo Benoiton

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Books
Chemistry of Peptide Synthesis
Edited by N. Leo
Benoiton. CRC
Taylor & Francis
Group, Andover
2005. 290 pp.,
hardcover
$ 139.95.—ISBN
1-57444-454-9
Leo Benoiton is an experienced peptide
chemist who has made fundamental
contributions to the chemistry of peptide
synthesis. This book addresses itself to
the principles and practice of the chemistries underlying the synthesis of peptides. In the authors own words, “the
focus is on understanding how and why
reactions and phenomena occur”. The
publication of such a book is timely, and
could make an important contribution to
the field of chemical peptide synthesis.
Peptide synthesis is a field with a
long and distinguished history—it is
almost exactly 100 years since the days
of the pioneer German chemists who
founded this field. Synthetic peptide
chemistry was a principal focus of the
energies of the worldwide synthetic
organic chemistry community for much
of the 20th century. The desire to
develop unambiguous methods for the
total chemical synthesis of peptide natural products drove significant innovation in synthetic methods, not just for
peptides but also for natural products in
general. Many of the giants of synthetic
chemistry made important contributions
to peptide chemistry. And the converse
is also true: peptide chemists made
important contributions to the synthesis
4234
of natural products. The synthesis of
peptide and peptide-like natural products still drives chemical innovation to
this day.
At the beginning of the 21st century,
the field of synthetic peptide chemistry
is in the early stages of a renaissance.
Several factors contribute to this
rebirth: the discovery of new classes of
diverse and potent peptide natural products, such as the conotoxins and the
cyclotides; a resurgence of interest in
peptides for use as human therapeutics;
and the use of synthetic peptides in the
total chemical synthesis and semi-synthesis of proteins. New developments in
synthetic peptide chemistry have always
been driven by the nature of the molecular targets in a given era: syntheses to
verify the “peptide theory” of protein
structure; the synthesis of protease substrates; synthesis of biologically-active
peptide natural products. This is true of
the recent past and is still true at the
present day. The development of the
“protease inhibitor” class of antiviral
therapeutics, which revolutionized the
treatment of AIDS in the form of
combination highly active anti-retroviral therapy (HAART), relied heavily on
innovations in chemical peptide synthesis. Some of the most important challenges currently facing the worldwide
biomedical research community, such as
vancomycin resistance in pathogenic
bacteria, will place extreme demands
on innovative synthetic peptide science.
The monograph that is the subject of
this review, Chemistry of Peptide Synthesis, by Leo Benoiton, is stronger on
chemical principles than on many of the
practical aspects of peptide synthesis:
for example, there is little or no discussion of modern methods for the
analysis of synthetic peptides. Analysis
is inextricably intertwined with synthesis. Peptide synthesis involves not only a
deep understanding of chemistry but
also a knowledge of by-products and
how they arise. In the past 15 years,
novel mass spectrometry (MS) techniques have revolutionized analytical peptide chemistry, particularly with the
recent introduction of affordable
HPLC-ion-trap MS instrumentation
that enables the routine detection, identification, and quantification of by-products formed during chemical peptide
synthesis. By choosing to ignore the
2 2006 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
practical topics of purification and analysis, the author has missed an opportunity to directly link the occurrence of byproducts in crude synthetic peptides to a
mechanistic understanding of how the
chemistry of peptide synthesis gives rise
to by-products, and thus of how they can
be minimized.
Much useful chemistry related to
peptide synthesis is well discussed in this
book, particularly in highly specialized
or advanced topics such as partial epimerization (racemization), coupling
methods/activation, and the molecular
origins of the aggregation/insolubility of
protected peptides. However, that utility
is offset by the incomplete coverage of
some practical aspects of synthetic peptide chemistry, by inaccurate description
of topics such as solid-phase peptide
synthesis—where much of the discussion is more than 20 years out of date—
and by uncritical repetition of obsolete
concepts with regard to important
chemical phenomena, particularly the
roles of the polymer matrix and solvation in solid-phase peptide synthesis.
Another topic that is not adequately
addressed is the role of chemical impurities in the resin polymer itself, which
cause side-reactions in stepwise solidphase synthesis. The figures in the book
are overly complex and confusing.
Finally, the book would have been considerably more useful with a comprehensive index, and the table of contents
could then have been simplified and thus
made more useful to the reader.
Peptide synthesis is a rich field of
chemistry with a vast and valuable
literature that is considerably underappreciated. Volumes E22a–e of the
Houben–Weyl series constitute a rigorous and complete compendium of synthetic peptide chemistry at the start of
the 21st century. However, there is
simply too much information in these
volumes. To complement them, we need
a concise and critical guide to the field of
chemical peptide synthesis, for the
novice and the expert alike. The book
reviewed here only partly meets that
need.
Stephen Kent
Institute for Biophysical Dynamics
University of Chicago (USA)
DOI: 10.1002/anie.200585369
Angew. Chem. Int. Ed. 2006, 45, 4234 – 4236
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