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Book Review Intermediate Organic Chemistry. By J. C. Stowell

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BOOK R E V I E W S
The Chemistry and Biochemistry of N-Substituted Porphyrim. By D . K . Lavallee. VCH Verlagsgesellschaft, Weinheim/VCH Publishers, New York 1987. x, 313 pp.,
bound, D M 89.00.- ISBN 3-527-266-93310-89573- 147-9
This monograph brings together in book form, for the
first time, the considerable knowledge which has been accumulated during the past two decades on the chemistry of
N-substituted porphinoids and their formation in biological systems. This survey of a particular aspect of porphin
derivatives should b e of interest to chemists and biochemists concerned with metalloporphyrins, heme proteins and
heme biosynthesis. In accordance with the nature of this
topic, the book consists of a “chemical” part and a “biochemical” part (containing four and three chapters respectively).
The first, introductory, chapter establishes the reasons
for the chemical, biological, and also medical interest in
N-substituted porphinoids.
The second chapter deals with the structures of some
particular series of N-substituted porphinoids and compares them with those of the porphyrins. In addition to the
detailed discussion of the structural effects of N-substitution in metal-free and metal-containing porphinoids
(which includes a considerable amount of data in the form
of tables, though unfortunately these are not always clearly
presented and appropriately titled), an attempt is made at
establishing a quantitative relationship between the bonding conditions and fundamental structural parameters such
as the N-hybridization and n-bond order in the porphyrin
ligands. Regrettably several errors in this chapter have escaped unnoticed, and adversely affect the understanding
of the material.
In the third chapter, which deals at some length with the
spectroscopy of N-substituted porphinoids, a large part of
the data now available is discussed and listed in numerous
(perhaps too many) tables. A strong point of this chapter is
again the clear way in which the data for porphinoids are
presented alongside those for the N-substituted porphinoids. A weakness, though, is that the important UV/VIS
absorption spectra (for example) have in most cases been
crudely reproduced by hand drawing. The more concise
and information-packed sections on reactions and on the
preparation of N-substituted porphinoids (Chapters 4 and
5 ) summarize the current state of knowledge in a clear and
understandable form, and also include a short but useful
collection of recipes for syntheses.
In the second, “biochemical” part of the book, Chapter
6 discusses in a lucid way the functioning of certain Nalkylated porphinoids as inhibitors in the enzymic incorporation of iron in the heme biosynthesis. Chapter 7 discusses the important mechanistic and structural aspects of
the formation of N-substituted heme derivatives in the
reactions of pharmacologically active substances, and of a
selection of other substances (including especially “suicide” inhibitors), with Cytochrome P-450. For the reader
interested in the topics covered, these two chapters provide
much well-presented information.
The first part of Chapter 8 describes, as other important
routes whereby N-substituted porphinoids are formed in
biological media, the reaction of hydrazines with heme
proteins, and rearrangement reactions of model comAnyew. Chem. Int Ed. Engi. 27J1988) N o I2
pounds. The second part of the chapter is essentially a recapitulation of a part of Chapter 5.
This remarkably long work, with a total of over 300
pages, ends with a detailed author index (1 1 pages), and a
subject index which, compared with the latter, is rather
lacking in content (less than 3 pages).
The book is a comprehensive source of information on
the chemistry and biochemistry of N-substituted porphinoids, which is nowadays recognized as an important aspect of porphinoid chemistry. Regrettably, the long-term
usefulness of the work is reduced by some conspicuous
weaknesses, such as the unsatisfactory layout of the text, a
succession of minor errors, and some misleading comments (especially in Chapters 2 and 3). The readability of
the book i s also marred by a lack of clear explanations in
the headings of some of the tables and in figure legends,
and by the use of abbreviations that are not explained.
Nevertheless, this monograph, which at present has no
competitor in the field which it covers, can be well recommended for the readership mentioned at the beginning of
this review.
Bernhard Krautler [NB 91 1 IE]
Laboratorium fur Organische Chemie
der Eidgenossischen Technischen Hochschule
Zurich (Switzerland)
Intermediate Organic Chemistry. By J. C. Sfowell. Wiley,
Chichester 1988. xv, 268 pp., bound, $ 46.50.--ISBN 0471-09899-X
Many of the experimental and theoretical innovations
developed in the last few decades, although eagerly adopted by chemists, have been slow to find a place in the
major textbooks and laboratory handbooks. Examples are
new spectroscopic methods, the concept of retrosynthesis,
and also working methods such as on-line literature
searching and molecular modeling.
Although topics such as these are very familiar to the
practising chemist, the student of chemistry usually only
learns of them at a late stage in his training, and often only
in a fragmented way. To set out to give students a systematic description of a few of these topics which have now
become so important is therefore a commendable objective. With this aim J. C . Stowell, in his book “Intermediate
Organic Chemistry”, has set out to bring together eight
logically interrelated topics so as to give an overall view of
organic chemistry. Following an introduction to basic
nomenclature the reader is familiarized with the technique
of searching the literature and with the principles of stereochemistry. This is followed by a three-part section on
methods for introducing and exchanging functional
groups, the formation of C-C bonds, and the concept of
retrosynthesis. The chapters which follow deal with methods for elucidating reaction mechanisms, possibilities for
physically influencing chemical reactions, and interdependent reactions. The book concludes with an introduction
to the interpretation of N M R spectra. Exercises at the end
of each chapter enable the reader to test what he has
learned; unfortunately, though, he must look up the cited
papers to discover the answers. Selected literature refer1737
ences extending up to 1985 are provided to facilitate more
advanced study.
The book is attractively printed and contains hardly any
errors (one occurs in the formula for dimethylsulfoxide on
page 72), although more elegant methods are available for
some of the reactions given (e.g. dehydrogenation using
Se, p. 84). The easily comprehensible style makes easy
reading.
It is, quite understandably, not possible to treat all these
topics with anything approaching completeness in 264
pages of text. Accordingly an attempt is not even made at
accounting for all the facts in a logical way, nor at dealing
in greater detail with the reaction schemes and rearrangements that are listed. It is perhaps on these grounds that
the author has avoided giving mechanistic interpretations
in the very long section on syntheses. Nevertheless, this reviewer sees the omission as a significant shortcoming,
since it means that the logical conception of the subject
which the author obviously sets out to promote is here disregarded, and arbitrarily selected facts and examples are
substituted for a proper understanding.
Chemists nowadays are self-taught as regards their
working habits. However, the work is neither a textbook
nor a course book in the conventional sense: it is, in Stowel”s words, a novel experiment. It is a n attempt to give
beginners in chemistry a view of the whole scene and the
interrelationships that exist; according to the introduction
it should be regarded as an aid to making progress in practical organic chemistry, a bridge from basic education into
the diversity of fields of more advanced chemical research.
Consequently the book is hardly suitable as a means of
acquiring a thorough knowledge of the topics that are
treated. Perhaps, therefore, it is just this fragmentary manner of presentation that makes the book especially suitable
for students who wish to test the knowledge acquired in
their studies. It can be thoroughly recommended for this
purpose.
Hartmut Laafsch [NB 914 IEI
Institut fur Organische Chemie
der Universitat Gottingen (FRG)
Biotechnology. A Comprehensive Treatise in 8 Volumes. Series Editors: H.-J. Rehm and G . Reed. Vol. 7a. Enzyme
Technology. Volume Editor: J. F. Kennedy. VCH Verlagsgesellschaft, Weinheim 1987. xii, 761 pp., bound,
D M 495.00/subscription price: D M 425.00.--ISBN 3521-25769-1
Reactions catalyzed by enzymes collectively form the
foundation of biotechnology. This volume on Enzyme
Technology is a very welcome addition to the mammoth
task undertaken by the editors and the publisher. Incidentally, although the title says the Treatise is to have 8 volumes, the series‘’] will really have 10 volumes when all the
work is done.
The aim of this volume is to provide for the reader a
review of the chemistry and biology of enzymes, and of
how enzymes are prepared and used. In this, the authors
have generally been very successful. One should not look
to this volume to learn about the economics of enzyme
[*I Cf. Angew.
1738
Chem. Int. Ed. Engl. 26 (1987) 1057
production, or for a perspective on the historical trends in
the industry or the market, or of the commercial potential
of enzymes. Use or potential use of enzymes for hazardous
waste treatment also could have received an emphasis. Despite this, the volume will serve as an extremely effective
and comprehensive resource for any scientific worker interested in enzymes.
There are 15 chapters in all in this volume, many of
them written by people who have made a good name for
themselves over the years with admirable research and development contributions. Three of the chapters (numbers
1, 2 and 6) should be seen as providing the fundamentals
of enzyme kinetics and molecular biology. These appear to
be geared not for the uninitiated but for those who are at
least somewhat familiar with the fields.
Another set of three chapters does a very good job of
describing how enzymes are made via fermentation and
then isolated and purified. The 146-page chapter on enzyme fermentations is in the nature of a scientific review
article, as are many of the other chapters in this volume.
The chapter has a good list of references spanning some 29
pages and generally has an “industrial” type outlook
which helps make u p for the lack of such data. Perhaps the
coverage of the “fermentation engineering” aspects could
have been better.
While there is some repetition in the two chapters on
small scale and large scale enzyme recovery, the chapters
are generally complementary. The chapters include some
excellent comments which will be of great benefit to someone starting work on enzyme recovery. The perspective
provided on ion-exchange chromatography is especially
good. This reviewer would have liked to see a better coverage of cell separation techniques, of enzyme production
economics, and of at least one flow scheme used in making
any of the large volume industrial enzymes.
Two highly readable and well written chapters are on
immobilized enzymes and immobilized cells. They provide
a very good perspective on the types and methods available for immobilization. The authors, who have otherwise
done some very good work in the field, could have elucidated why some of the approaches to immobilization have
been successful on the industrial scale and why others
have not. Synthetic enzymes, or the use of polymers and
macrocyclic compounds to achieve “enzyme like” catalysis
is the subject of another brief and readable chapter.
A chapter on the engineering aspects of enzyme reactor
systems is comprehensive and well written. Here again, repetition of some of the enzyme kinetics already covered in
Chapter 1 might have been avoidable.
How enzymes have been or can be used is the subject of
a group of four chapters by authors severaI of whom have
outstanding credentials. The chapter by veterans Reed and
Peppier on the use of enzymes as food or animal feed processing aids shows one has to appreciate the terminology of
the industry, be it baking or starch processing or brewing
or dairy or wine or meat or whatever. The emphasis is on
process recipes/procedures rather than on the chemistry
involved. A gem here is a listing of some costs of enzymebased processing; e.g., the cost of isomerizing 100 kg dextrose to fructose by a bacterial isomerase is 33-66 US
cents. This reviewer would have liked to see more such
perspectives by other authors in the volume.
Enzymes in their “free” (soluble) or immobilized form
find many uses in the pharmaceutical and chemical industries and are discussed in two chapters. The use of enzymes
in the making of amino acids, organic acids, antiviral compounds, coenzymes, peptides such as insulin and asparAngew. Chem. Ini. E d . Engl. 27 (1988) No. 12
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