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Book Review The World of Peptides. A Brief History of Peptide Chemistry. By T. Wieland and M. Bodanszky

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most of which have appeared during the last decade
(35 during 1990), it offers an extensive reference source with
particular emphasis on the chemo-, regio-, and stereoselectivity of the reactions.
The book is divided into three parts. The first part, consisting of 13 pages, briefly describes the relevant properties
(solubility, stability, reactivity) of the most commonly used
alumino- and borohydrides, and of a few boranes. The second part (1 26 pp.) deals with reductions of the most important functional groups. This main part of the book covers the
reductive scission of CX, CO, CN, and CP single bonds, and
the reactions of the title reagents with CC, CO, and C N
double bonds, and with CC and CN triple bonds, and ends
with a chapter on the reduction of other substrates (N-, Hg-,
Pd-, S-, P-, Si-, and B-containing compounds). The third
part (12 pp.) gives a tabular survey of reductive preparations
for the most important functional groups, listing the products, educts, reagents, and relevant sections in the book.
These synoptic tables arranged according to the structure of
the product, together with the list of contents subdivided
according to the structure of the substrate and an additional
1 1 -page index organized according to reaction types, enable
the reader to readily locate particular transformations of
interest.
The examples chosen to illustrate the selectivities include
numerous synthetically relevant polyfunctional substrates,
making up a very useful compilation. The main strength of
the book undoubtedly lies in the detailed discussion of the
differential reactivities of various functional groups towards
alumino- and borohydrides, and the clear information that is
given regarding suitable chemoselective reagents for each
case. An appropriate amount of space is also devoted to
substrate- and reagent-induced stereoselective transformations, but the pleasure in reading these sections is marred for
the reasons explained below. Nowhere is there any mention
of yields; however, a few random checks in the original
papers that are cited indicate that the reactions described
give high yields.
Unfortunately, the book contains many errors that could
easily have been avoided by conscientious proofreading.
These include simple slips (for example, p. 39: “most hindered double bond” instead of “least substituted ...”, p. 99:
“trapping of the aluminum enolates obtained from alkyl
halides” instead of “ ... with alkyl halides”, p. 143: “to treat
the sulfones” instead of “... the sulfoxides”), wrongly or
incompletely drawn structures (for example, p. 26: sultone
instead of sulfate, p. 32: free alcohol instead of TMS-ether,
pp. 36 and 148: primary ozonide instead of secondary
ozonide and, accordingly, wrong products shown, p. 94:
missing imide nitrogen atom and missing CH, group in the
chiral auxiliary, p. 52: stereochemistry of the ring junction in
the decalones omitted, p. 97: relative configurations of the
3.5-dimethylcyclohexanones not shown), inappropriate descriptions (e.g. p. 29: “the reaction proceeds with configuration inversion” and p. 37: “the reaction can be regioselective”, as comments on reactions that do not show the
selectivities referred to, or p. 71 : “the reduction follows the
Felin-Anh rule”, as an explanation of the stereoselective
reduction of ketones that do not have a stereogenic center at
the CI carbon atom), and misleading representations, which
are frequent (of all places) in the important chapters on the
stereoselective reduction of ketones (for example, pp. 49, 50,
54: confusion between the major and minor products in the
reduction of C-22 ketones of the steroids series-here also
the methyl group on C-20 is sometimes missing, pp. 62-63:
interchanging of the major and minor products in the reduction of 2-acyl-l,3-oxathiones and the wrong enantiomers
A n g w . Chem. i n ( . Ed. Engl. 1992, 31, No. 11
6
shown, p. 68 : the irrelevant statement that “the two conformations C, and C, are equally populated”, where one is
dealing with different reactivities). Readers interested in the
stereoselective synthesis of steroid side chains or in applying
Eliel’s method for the enantioselective preparation of a-hydroxyaldehydes must definitely consult the original pubhcations.
To summarize, therefore, this book leaves one with a
mixed impression; a thorough revision would be necessary
before this reviewer could agree unreservedly with the recommendation by H. C. Brown in the preface that “this book
should be in the personal library of every chemist engaged in
organic synthesis”.
Peter Metz
Organisch-chemisches Institut
der Universitat Miinster (FRG)
The World of Peptides. A Brief History of Peptide Chemistry.
By 7: Wieland and M . Bodanszky. Springer, Berlin, 1991.
XJI, 298 pp., hardcover DM 198.00.--ISBN
3-54052830-X
When, in 1901 in Berlin, Emil Fischer prepared glycylglycine, the first free “peptide”, no one guessed that this
compound marked the beginning of the history of a fascinating class of substances. Peptides constitute the link between
amino-acids and proteins. The great variety of peptide structures includes compounds with remarkable biological activities. Many important hormones, antibiotics, toxins. sleep
regulators, pain regulators, immunostimulants, immunosuppressants, antitumor and anti-AIDS agents, and a variety of
other active substances, are peptides.
This “world of peptides” is described in the book by
Theodor Wieland and Miklos Bodanszky. The ten chapters
(298 pp.) are as follows: 1. Introduction. Aminoacids and a
Few Early Paradigmatic Peptides; 2. Synthesis of Peptides.
The First Epoch; 3. The Era After Emil Fischer. The Carbobenzoxy Group, Max Bergmann and his Scientific Circle;
4. A Second Breakthrough: New Methods for the Formation of the Peptide Bond; 5. A New Technology: Solid Phase
Peptide Synthesis; 6. Structure Elucidation; 7. Peptide Hormones; 8. Biologically Active Fragments of Proteins;
9. Biologically Active Peptides from Microorganisms and
Fungi; 10. Peptide Research Around the World.
Reading this highly interesting account one is aware on
every page that the authors are thoroughly at. home in this
world. Indeed, in their scientific careers they have had a part
in shaping the history of these developments, through their
fundamental contributions to experimentation and to the
literature. The first few chapters describe in detail the work
of the founders of peptide chemistry (Fischer, Curtius, Abderhalden, Leuchs, Bergmann, and others) and of the pioneers of the post-war period (Du Vigneaud, Rudinger, Merrifield, etc.). One learns more about the difficult relationship
between Fischer and Curtius, and about the temporary shift
of the center of gravity of peptide research from Germany to
the USA. Pioneering advances are related to the subsequent
developments in an admirable fashion; for example, the discovery of the Leuchs anhydrides is linked to an excellent
review of later work on the chemistry of NCA and
polyamino-acids, and that of the benzyloxycarbonyl residue
by Bergmann and Zervas is linked to an account of work on
protecting groups during the years that followed. The rapid
development of peptide chemistry after the Second World
War led to numerous innovations in methods of synthesis
VCH VerlugsgeseffschufimbH. W-6940 Weinheim, 1992
OS70-0~3319Zjlll~-1535
$3.SOf.Z5I0
1535
and analysis, to the discovery of many new naturally occurring peptide structures, and to the elucidation of a variety of
structure-activity relationships. The careful choice of subject
matter covers all the important facts and highlights. However, it seems to this reviewer that the application of genetic
engineering methods to peptide synthesis has not been treated in adequate detail. One can hardly accept that a few more
pages here would have exceeded the planned length of the
book.
In Chapter 10 one learns that research in peptide chemistry is now being carried out in 27 countries throughout the
world (the names of about 800 peptide chemists are listed,
and the appendix contains photographs and short biographical notes on about 60 of the field’s “klite”).
A comprehensive bibliography at the end of each chapter
facilitates quick access to the original publications. Other
useful information (not only for the expert) is given in a
chronological list of international symposia on peptides
(Ch. 3, Ref. 42), and in references to the standard works on
the subject.
The “Brief History of Peptide Chemistry” announced in
the book’s subtitle turns out in practice to be a valuable
monograph on the topic. This considerably broadens the
potential readership. Scientists with an interest in the history
of the subject, especially chemists, biochemists, medical scientists, pharmaceutical chemists, and students of all these
disciplines, will find here a wealth of information that could
otherwise only be gathered with a great deal of effort. Altogether this is a book that belongs in every specialist library,
and that everyone concerned will need to have read.
Hans Jeschkeit
Institut fur Organische Chemie
der Universitat Halle (FRG)
Ashwell. Research
Molecular Electronics. Edited by G. .l
Studies Press, Taunton (UK)/Wiley, Chichester, 1992. X,
362 pp., hardcover E 44.50.-1SBN 0-86380-125-O/O-47193386-4
Molecular electronics is an intriguing term, which can be
understood to include several quite different fields of research. Essentially, however, two major areas can be distinguished. Firstly there is the search for molecular materials
that can be used in electronics or microelectronics to make
components with improved functions. Secondly one can understand it to cover various investigations, some of which
involve highly speculative ideas, with the aim of developing
a form of electronics based on individual molecules. The
hope here is that an element performing an electronic function can be incorporated within a single molecule or a small
number of molecules. It is this latter possibility in particular
that has seized the imagination of researchers. The book
reviewed here deals only with the first of these problem areas, and even here it does not claim to cover the whole topic.
A more appropriate title would therefore have been something like “Molecular Materials for Electronics-Selected
Topics”.
The six chapters are essentially independent of each other,
and cover several aspects that are important in relation to
potential applications of molecular materials in electronics.
The first chapter, “Molecular Electronic Materials”, by G. J.
Ashwell, I. Sage, and C. Trundle, begins with a 27-page
survey of such interesting topics as photochromism, electrochromism, organic conductors, superconductors, and
nonlinear materials. The most important areas of applica1536
0 VCH
Verlagsgesellschafl mbH, W-6940 Weinheim, 1992
tion are in optical data storage, molecular rectifiers, and
frequency doubling. A review as short as this is inevitably far
from complete, and many important publications do not
appear in the bibliography. This is followed by a 30-page
review of the physical and chemical properties of liquid crystals, which has no obvious relevance to the theme of the
book. The second chapter, on “Conjugated Polymers”, by
M. F. Rubner, explains conductivity in polymers by introducing the concept of solitons and polarons, then discusses
aspects such as stability and processing behavior, and describes applications of conducting polymers as active layers
in electronic components, in Schottky junctions, and in fieldeffect transistors. In Chapter 3 on “Langmuir-Blodgett
Films”, I. R. Peterson first gives a detailed description
(60 pp.) of the preparation and characterization of these
films, which allow the development of a “molecular architecture” and make it possible to arrange molecules in well-defined structures. This is followed by 15pages devoted to
potential applications (thin insulating films, dielectrics in
capacitors, in lithography, and in nonlinear photonics), the
general impression being rather pessimistic. In Chapter 4 on
“Nonlinear Optics”, S. Allen gives a good overview of the
prospects for measuring nonlinear optical properties of organic materials and influencing these chemically, and also of
incorporating such molecules into a suitable matrix. However, no practical applications in electronics are cited, which
probably reflects the true situation. In Chapter 5, “Piezoelectricity, Pyroelectricity and Ferroelectricity”, J. Sworakowski gives an introduction to this group of topics, with
particular emphasis on molecular solids. Although there are
potential applications in molecular electronics, for sensors,
storage devices, and similar purposes, the author’s view is
that, with the exception of polar monomers, these are unlikely to be realized in the near future. The final chapter by K.
Firth on “Holography” gives a short and superficial account
of the main features of holography, without really relating
this to molecular electronics. Recent developments such as
holography based on bacteriorhodopsin are not mentioned.
It is not clear for whom this book is intended. The six
chapters contain little that will be new to specialists, although they do provide something of an overview of this
broadly interdisciplinary field of research. The interested
non-specialist, although not finding as much in the book as
its title appears to offer, can nevertheless learn something
about several interesting aspects of materials research.
Hans Christoph Worf
Physikalisches Institut
der Universitat Stuttgart (FRG)
The Science of Crystallization. Microscopic Interfacial Phenomena. By K A . Tiller. Cambridge University Press,
Cambridge (UK), 1991. XXX, 391 pp., hardcover
&40.00.-ISBN 0-521-38138-9/paperback E 15.00.-ISBN
0-521-38827-9
The two monographs “The Science of Crystallization.
Macroscopic Phenomena and Defect Generation” and “The
Science of Crystallization. Microscopic Interfacial Phenomena” together form a complete set from this publisher. As the
author indicates in his preface, they are suitable as textbooks
for students at postgraduate or advanced undergraduate levels in materials science, chemistry, or related subjects. These
compact and straightforwardly presented volumes are themselves a crystallization of Tiller’s long experience in teaching
and research, during a period of far-reaching developments
0570-0X33~92jllll-l536$3.50+ ,2510
Angew. Chem. I n t . Ed. Engl. 1992, 31, No. 11
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