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Molecules that Changed the World. By K.pC. Nicolaou and Tamsyn Montagnon

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Angewandte
Books
Chemie
Molecules that Changed the World
By K. C. Nicolaou
and Tamsyn Montagnon. Wiley-VCH,
Weinheim 2008.
366 pp., hardcover,
E 34.90.—ISBN
978-3-527-30983-2
Molecules That Changed the World
provides a historical perspective on
organic molecules and their impact on
mankind. This captivating saga of arduous chemical isolation, often from natural sources, intricate structural characterization, elegant synthetic modifications of small molecules and the subsequent study of their properties spans
almost 200 years, from the first synthesis
of urea and acetic acid in 1828 and 1845,
respectively, to the latest drugs. The
importance of each class of compound in
our world is well exemplified with
perfumes, dyes, textiles, agrochemicals
and, most importantly, medicines. With
the inclusion of varied historical details
dating as far back as ancient Greece and
Egypt along with portraits and colorful
illustrations related to those scientific
studies, the authors pay tribute to the
ingenuity, passion and dedication of the
many scientists who were involved with
these chemical adventures. The intricacies of our science and the strong
positive impact it has had on society
are clearly demonstrated throughout the
book and should serve as a source of
inspiration for many, from young students to seasoned scientists.
The first chapter introduces the
reader to the basics of chemistry, from
the atoms and the periodic table to
simple molecules like water, amino
acids and sugars to the building blocks
Angew. Chem. Int. Ed. 2008, 47, 3309 – 3311
of life, nucleic acids and proteins. Natural products of critical importance to
mankind are then introduced, illustrating the concept of total synthesis by
nature itself. As it is the case throughout
the entire book, molecules are colorfully
depicted in both two and three dimensions (ball & stick and space filling
models) and the text is accompanied
by a multitude of figures, schemes,
historical artifacts and portraits of the
scientists, many of these floating above
pictures of nature or everyday life, but
always related to the scientific subject.
The book is then chronologically
organized in chapters 2–32, each centered on the discovery and studies of an
important molecule or class of molecules. Each of these cornerstone molecules is the subject of an essay that
encompasses the history of its discovery
and the ramifications it had, both in
terms of scientific progress and impact
on society. The authors not only
describe the discovery and synthesis of
these molecules from a chemist/s perspective they also delve into the biological processes in which they are
involved. Chemical modifications leading to more recent and often more
efficient agents are also described. For
example, in the aspirin chapter, the role
of cyclooxygenases (COX-1 and COX2) in the arachidonic acid cascade along
with the importance of PGI2/TXA2
balance in platelet aggregation are well
described, both in the text and graphically in separate figures. Selective COX2 inhibitors are then discussed and
compared to aspirin in a very objective
manner, highlighting not only the
advances scientists made following the
footsteps of H. Kolbe and F. Hoffmann
but also the challenges associated with
the discovery and introduction of new
medications. In the camphor and terpineol chapters, the authors highlight the
importance of chemical discoveries
toward the development of scents, inks
and most significantly perfumes, once
again with the relevant reference to
historical facts and pictures. The
haemin chapter introduces the reader
to natural and synthetic dyes and their
impact on the textile industry while the
resiniferatoxin chapter presents the science of taste and spices.
A series of chapters (9–32) is then
dedicated to natural products of increas-
ing structural complexity: quinine, penicillin, ginkgolide B, taxol, FK-506 and
vancomycin, to name just a few. Their
elegant total syntheses and importance
in medicine and society are described in
detail. A number of medical approaches
to diseases or conditions such as
malaria, pain, bacterial infections,
asthma, cancer, atherosclerosis, organ
transplantations and birth control are
explored in these pages. A few chapters
contend with marine natural products,
especially toxins such as palytoxin and
brevetoxin B and cytotoxic agents such
as ecteinascidin 743 and spongistatin,
along with their involvement in natural
processes such as spectacular red tides.
Leaving the field of natural products
in the last two chapters of the book, the
authors review small molecule and biologics drugs. After a brief overview of
the drug discovery and development
process, highlighting the different roles
of chemists, a series of important medication classes are explored. Again their
tremendous impact on society is made
obvious.
The book also contains three complete indexes of images, persons and
subjects.
Not forgetting the central importance chemistry has had in all the
aforementioned advances in our society,
the authors also take the time to further
develop a number of theoretical or
practical aspects of chemistry, ranging
from aromaticity, radicals and ionophores to the Diels-Alder, aldol,
Grignard, hydroboration, asymmetric
hydrogenation, epoxidation/dihydroxylation, palladium-catalyzed cross-coupling, and olefin metathesis reactions,
without missing important concepts
such as retrosynthetic analysis, protecting groups, and split-and-pool and solidphase strategies for combinatorial
chemistry. Each of these subjects is
explored outside the main text, in a
separate section, inserted in the appropriate chapter.
Limited reference to the primary
literature is made at the end of each
chapter and, in cases where multiple
syntheses were accomplished by different scientists, more comprehensive attribution would have been appropriate.
The modular design of the book
makes it possible to read in installments
and in almost any order, based on
& 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
3309
Books
personal preference. The insertion of
technical mini-topics in boxes outside
the main text also allows for reading at
multiple levels based on various degrees
of expertise. In addition, the “coffee
table” format and the inclusion of many
pictures and historical artifacts are very
entertaining and invite the reader to leaf
through again and again; this book is
simply hard to put down!
Molecules That Changed the World
is nothing short of a “chef d/oeuvre”
that will make chemists proud of their
profession, a much needed and difficult
task in our current society. This book
will no doubt educate, inspire and motivate anyone with an interest in science
and its impact on mankind, from the
young science student and interested lay
person to the accomplished scientist or
practitioner of life sciences.
History of Strychnine, suggests an
almost universal appeal, ranging from
natural products chemists to historians
of chemistry to those interested in the
development of modern medicine to
lovers of suspense thrillers. Buckingham, an organic chemist, is the founding
editor of the Dictionary of Natural
Products, is editor of the Dictionary of
Organic Compounds, and recently published the very well received book
Chasing the Molecule. Thus he is well
positioned to write the story of strychnine and its cousin brucine, both of
which occur in plants of the Strychnos
genus.
Rainer E. Metternich, Philippe G. Nantermet
Merck Research Laboratories
West Point, PA (USA)
DOI: 10.1002/anie.200885602
Bitter Nemesis
The Intimate History of Strychnine.
By John Buckingham. CRC/Taylor &
Francis, Boca Raton
2007. 320 S., softcover, £ 19.99.—
ISBN 978-1-42005315-9
The world of the history of chemistry is
quite small, and yet at the same time it
encompasses everyone. Many researchers write review articles that are certainly part of the history of chemistry.
And the introduction of every research
article is, in its own way, a mini-history,
with references of the topic. Yet few of
us practicing chemists read the specialized journals of historians of chemistry,
let alone participate in their symposia.
John Buckingham/s book Bitter
Nemesis, with the subtitle The Intimate
3310
www.angewandte.org
Buckingham is astute and meticulous in his research. He fills this story
with carefully documented facts and
informative anecdotes, all within the
context of the time periods discussed.
In 1753, the Swedish botanist, physician,
and zoologist Carl Linnaeus proposed
the genus Strychnos for a group of trees
and shrubs that shared various characteristics, including being both poisonous
and bitter (Greek st1#fHz). Nux
vomica, the powdered seeds of S. nux
vomica containing strychnine and brucine, was misleadingly known as the
vomiting nuts. However, the powder
does not induce vomiting, as many
physicians in the 19th century had
hoped based on its name. Rather,
vomica is Latin for an ulcer, and the
term originates from the use of nux
vomica in ancient Arabic medicine to
treat sores. Consequently, the medicinal
use of nux vomica or—as medicinal
chemistry advanced in technique if not
in knowledge—of impure and later of
pure strychnine apparently caused more
damage than cure in the unfortunate
patients. Their physicians did survive the
treatments, however.
Buckingham presents these early
“medical” experiences so clearly and
dramatically that one almost has the
feeling of being in the moment. He
explains Paracelsus/s notion “that every
& 2008 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
disease should have a cure somewhere
in the natural world”, and “the belief of
many doctors even into the nineteenth
century that all diseases, except mental
diseases or those caused by debauchery
or other excess, were forms of poisoning”. In particular, regarding substances
derived from nux vomica, even though
they did not cause vomiting, he comments that “Taking into account the
other main contemporary stratagems;
purging, blistering, vomiting and the
lancing of boils, it is clear that virtually
all the techniques meted out by the
eighteenth-century physician had to do
with expelling noxious matter from the
body”. Thus, strychnine—having such
powerful pharmacological properties,
i.e., itself being a poison—was believed
to be a powerful medicine!
Buckingham surely must have a
great sense of humor. Frequently, I
found myself in a deep chuckle, as
when he quotes from The Count of
Monte Cristo, “KIt is very fortunate/, she
observed, /that such substances could
only be prepared by chemists; otherwise, all the world would be poisoning
each other.K” Elsewhere, he comments:
“In 1821, it was ruled that a man of
science, /without recognized learningK
and basing his arguments on the novel
process of experimentation, had no
more status than a mechanic. This
decision settled for many years the
status of chemists, despite the fact that
they frequently made large sums of
money as expert witnesses in litigation”.
Often, my chuckles were more uneasy
than light-hearted! “Nux vomica
powder was therefore an extremely
dangerous cumulative poison with
wildly unpredictable effects; the most
dangerous medicine that has ever been
administered to human patients, despite
some stiff competition”—“For some
physicians, strychnine became the WD40 of Victorian medicine”—“When all
else had failed and the patient was on
the way out, strychnine could be used to
resolve things, one way or the other”.
As described by Buckingham,
strychnine became the poison of
choice, both for real-life murderers and
for authors such as Agatha Christie and
Alexandre Dumas. The growing instances of deliberate strychnine poisoning
led to the development of methods for
forensic applications. Thus, strychnine
Angew. Chem. Int. Ed. 2008, 47, 3309 – 3311
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