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Book Review D-Glucose und verwandte Verbindungen in Medizin und Biologie (D-Glucose and Related Compounds in Medicine and Biology). Edited by H. Bartelheimer W. Heyde and W

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The first volume does justice to the promises of the prospectus. We look forward with interest to the early publication of
H . Lnhliort
[NB 611 I € ]
the later volumes[*].
[ * ] Editorial note: Volume 2 has now appeared. Volume 3 is
due to appear in September 1967 and Volumes 4 and 5 should
be available in January 196s.
Trivialnarnenkartei-1 .Erganzungslieferung (Card 1ndex ofTrivial Names - 1st Supplementary Issue). Verlag Chemie
GmbH.. WeinheimiBergstr. 1966. 1088 cards, DM 60.-.
In 1964, Verlag Chemie began to compile a card index of trivial names [I]. The first issue contained 8000 cards. Each card
bears a number giving its position in the alphabet, the trivial
name in question (in German on the left, in English on the
right), the structural formula of the compound with stereochemical details (where known), the empirical formula, and a
reference to a handbook or journal. It is explained that the
aim of this card index is not to foster trivial names, but to
provide information wherever none is supplied by the trivial
name. For example, it should be of assistance to anyone who
does not know what palustrinic acid Centaur X4, or munetone is. However, he should also possess the first supplementary issue, which contains to88 cards’and which has just been
published. It also contains a list of addenda to the cards of
the first issue
Further supplementary issues are plrlnne’d, and it is really
unnecessary\ro emphasize the vame of this card index. Those
who already have it at their diSbosal will have learnt to
treasure it, and those who do not yet know it should acquire
it as soon as possible for the sake of easy reading in chemical
literature.
H. Griinewald
[NB 581 IE]
[I] Cf. Angew. Chem. 78, 344 (1966); Angew. Chem. internat.
Edit. 5, 326 (1967).
Reactiones Organicae. Organische Reaktionen und Methoden.
(Organic Reactions and Methods.) By H. J. Ziegler. Georg
Thieme Verlag, Stuttgart 1967. Basic stock (12 batches):
about 3000cards; about 250cards per batch. Price per batch:
D M 220.-; 20% reductionwhen thecompleteworkisordered.
A greet deal has been done to classify chemical literature in
such a way that any desired information can be found quickly
and as fully as possible, but without padding. A new attempt
to make the knowledge of preparative organic chemistry
readily accessible is the card index entitled “Reactiones Organicae” that has been compiled by H. J . Ziegler. This index
contains all the procedures from “Organic Syntheses”, all
the reaction types from “Organic Reactions” and (with the
exception of the ring-closure reactions) from “Cahiers de
Synthese Organique”, and all the reactions from “Namenreaktionen der Organischen Chemie”. The basic stock contains 3000 cards. (Eight batches containing a total of 2000
cards have been issued so far.) It will be continuously
supplemented and updated by further batches.
The card index consists of punched cards, each of which
describes a reaction or asynthesis (sequence of reactions). In
the heading on the front of each’ card, the reaction type is
given on the left, the reaction conditions a n d reagents on the
right, and references t o Houben-Weyl and to “Cahiers” in
the center. In the field below the heading, the reaction described is characterized by a complete formula, data on
yields, and a Qterature reference. On the back of each card is
the name of the reaction prcduct, a short account of the
procedure in German and in English, and a list of compounds
(with yields) tlat can be prepared in the same way.
The “knack” of “Reactiones Organicae” is that any desired
reaction is first reduced to a reaction type. For example,
suppose that one wishes to find the possible methods for the
oxidation of secondary amines to azomethines. This reaction
can be represented in its simplest form by the equation
\
CH-NH-
816
\
+ ,C=N-.
Code numbers for the partial formula on the left (starting
group) and for that on the right (product group) are then
found from two formula indexes supplied with the cards
in the form of loose-leaf books. These numbers then enable
il selector instrument to extract all the cards that describe
such reactions. For more specialized problems, code numbers characterizing the reaction conditions and the overall
constitution of the product are available.
The entire system is both cleverly conceived and easy to use.
Aids (program blocks, color code) are provided to facilitate
further the use of the card index and to make it foolproof
even for assistants. The greatest advantage of “Reactiones
Organicae”, however, is the fact that no notation that is not
familiar to the chemist, no hypotheses on reaction courses,
and no classification of reactions are included, and that
neither nomenclature problems nor language problems arise.
Thus “Reactiones Organicae” is the ideal literature card
index for the organic chemist engaged in preparative work.
H. Griinewald
[NB 519 I€]
o-Glucose und verwandte Verbindungen in Medizin und Biologic (D-Glucose and Related Compounds in Medicine and
Biology). Edited by H. Bartelheimer, W. Heyde, and W .
Thorn. Ferdinand Enke Verlag, Stuttgart 1966. 1st Edit.,
xv, 1126 pp., 173 figures, 124 tables, cloth DM 228.-.
Contrary to what one might expect from its title and size,
this book cannot be summed up in the words “all about
glucose”. It is not a sort of monograph in which one can
quickly find out all about a certain chemical or biochemical
property of this sugar or of one of its derivatives, but is
rather a eulogy on this compound and its direct and indirect
biosynthetic transformation products and precursors. The
subject matter covered in the book is by no means narrow.
For example, it contains long chapters on “The oxidative final
stage of metabolism”, i.e. on the transformation of the transformation products of the products of transformation of Dglucose, on “The quantum chemistry of photosynthesis,
automatically written”, where only a few of the compounds
described are ultimately converted into or formed from
glucose or glucose derivatives. One could, if one were so
inclined, say that any carbon compound found in plant or
animal cells or in microorganisms is a potential precursor or
transformation product of D-glucose, provided that the
organism in question can use glucose as a source of carbon.
The editors are therefore forced to make a selection, unless
they wish to compile a “Beilstein” of natural products. The
question that arises now is whether the selection made was a
good one. Closer examination shows that is it impossible to
give any general answer; in the 45 chapters by 54 authors, the
problem of relatedness of the subject under discussion to
glucose is solved in various ways.
Almost half of the work is devoted to pharmacological,
pathophysiological, and clinical aspects. Several articles in
this part deal with the role of glucose in particular and/or of
hydrocarbons in general in disease and in the function of
various organs (endocrine disorders, diabetes mellitus,
kidneys, liver, heart, lungs, joints, brain, skin, eyes, throat,
nose, ears, tumors), in surgery, pediatrics, and psychiatry,
and in sport. These chapters offer a great deal of valuable
information to those with no medical training.
The general chemical and biochemical principles of these
special chapters are, unavoidably, not always in agreement
with the latest fundamental developments, which always
penetrate into the more specialized sectors of a science only
after a certain time lapse. Unfortunately, the same is also
true of many of the fundamental articles in Section D, “Biochemistry and Physiology” (283 pages).
The length of this time lapse will not be discussed for the
various articles. An average minimum value can be estimated
from the fact that almost the entire molecular biology vocabulary (e.g. induction, repression, operon, messenger, alloAngew. Chem. internat. Edit. Vol. 6 (1967)/ No. 9
sterism, end-product inhibition, isozyme, multienzyme complex) is missing from the index. “Enzyme induction” is
mentioned in the index, but the passage referred to is simply
the unsupported statement that “The adrenocortical hormones increase glyconeogenesis by true enzyme induction”.
Section C , which deals with “Formation, occurrence, and
importance in plants and microorganisms” (3 articles, 67
pages), concentrates o n the discussion of photosynthesis (47
pages). The only article on microorganisms, “Constituent
hydrocarbons of the bacterial cell” (20 pages), shows relatively little relation to glucose, but presents a well-rounded
account of this field, which is complex from the point of view
of structural chemistry. There is no general article on microorganisms, such as might be expected from the title of the
book. The 113 pages of Section B, “Methods of determination” (2 articles) will probably be the first pages of the library
copy to become grease-spotted and dog-eared; the material
in this section appears to be full and carefully written, with
a good understanding of the subject. We finally come to an
introductory chapter, “Chemistry and pharmaceutical chemistry”. This chapter presents a brief outline of carbohydrate
chemistry, in which the problems of conformation, which are
particularly important in connection with the enzymatic reactions of sugars, are dealt with in detail. The concebt of
instability factors and Hassel-Ottar and ,A2 effects a r e e i
plained with the aid of molecular models.
The air oxidation of D-ghCgSe to D-gluconolaolone is discussed as an “Inference from the conformational behavior”, and
is compared with the enzymatic oxidation of .glucose
phosphate. The example is i k h o s e n . Contrary to the statement that the enzymatic dehydrogenation “evidently depends on the axial position of the hydroxyl group on C-1 of
the a-glucopyranose” in the same way as the chemical hydrogenation, glucose 6-phosphate (like all aldoses) is in fact
enzymatically oxidized only in the form. The correct chemical parallel to this should therefore be oxidation with bromine, in which oxidation takes place at the equatorial hydroxyl
group of the form.
P
P
There is no doubt that this book contains a great deal of
valuable information that may be useful to anyone who is
concerned with the biochemical, physiological, and medical
aspects of sugars. However, just as a good memory depends
on storage capacity and ability to recall, so the value of such
a large handbook depends on whether the desired information,
which is assumed to be present, can be found quickly and
reliably. The index is not the best for ease of recall. This may
be the type of index that must be expected in the future when
indexes are compiled by machines. It is otherwise difficult to
understand e.g. why methylglucoside (pp. 24 and 25), a-Dmethylglucoside (pp. 22 and 58), ~-~-methylglucoside
(p. 22),
a-methyl-mglucopyranoside and P-methyl-D-ghcopyranoside (p. 106) are listed separately in the index, though the substances are simply anomers of the same compound. The last
two are given in English, since they occur in a n article written
in English. The German keyword “Gluconeogenese” is given
in 15 different contexts and with 26 page numbers. However,
none of these pages gives a clear definition mentioning the
main enzyme reactions o n which the phenomenon depends.
Nevertheless, this definition is given clearly and precisely in a
short section of an article written in English. To find this in
the index, one must look under “glyconeogenesis”, which
comes seven pages after “Gluconeogenese”.
What is “maltotriosyl”? It is an orthographic radical that
owes its existence to the English terminology (without covalent or coordinate bond?) in the phrase “which transfers
maltotriosyl residues”.
Nevertheless, the enthusiasm that filled the editor and the
authors and that led to the creation of this work is justified.
g glucose and related compounds form a family of imposing
might, which plays a n important part in all branches of
animate nature, and which must fascinate the specialists in
every phase of the development of our science.
K. WaIIenjels
[NB 585 IE]
Angew. Chem. internat. Edit. J VoI. 6 (1967) J No. 9
Laboratory Handbook of Toxic Agents. Edited by C. H. Gruy.
The Royal institute of Chemistry, London 1966. 2nd Edit.,
ix, 190 pp. Paperback 24s; 18s to Royal Institute of
Chemistry menbers.
The book comprises five sections: 1. General hazards involved
in the handling of chemicals (12 pages). 11. General precautions and accident prevention, including safe disposal of
chemicals (pp. 15-23). 1”. First aid in cases of skin-contact
and internal poisoning, including the different techniques
of applying artificial respiration (PO. 27-35).
IV. The main section (pp. 39-166): 250 toxic gases, reagents,
and solvents are listed in alphabetical oder (Acetaldehyde to
Xylidine). The acute and chronic sings of poisoning are listed
in a few key phrases for each substance, as are first aid
measures, the TLV(MAC) value, and the necessary warning
labeling. Each substance has about half a page devoted to it.
Synonyms are referred back to the appropiate passages under
their ‘approved’ names. Occasionally the nomenclature (in
the absence of formulae) is difficult to understand for German
readers, e.g. ‘methyl chloroformate’ ; ‘ethyl chloroformate’
at least has ‘ethyl chlorocdrbonate’ appended In parenthsis.
Chapter V (pp. 169-188) deals with the precautions to be
taken during handling of radioactive materials, and contains
I4 literature reference$
The book attempts to ahow. how careful handling of chemicals
can prevent accldents-and when these occur, how further
chanage can be @Voided.A page prefaced to the text is to be
filled in by the user with the name of the deputy safety
officer, the nearest hospital for casualties, ambulance, doctors, and persons trained to give artificial respiration, as well
as telephone numbers of poison information centers. The
glossary on the two concluding pages is evidently intended for
chemical laboratory workers, in that it explains simple
medical terms such as anemia, leukemia, bronchitis, urticaria,
etc. Unfortunately the book has no index.
The toxicological data contain mistakes - despite the collaboration of Ethel Browning. Thus fluorinated hydrocarbons
are described as liver poisons but not so chloroform. N o
warning of the increase in the potency of alcohol intoxication
following exposure t o aniline and nitrobenzene is given,
though this is a n important matter for the layman. The book
is suitable for obtaining rapid information about potential
risks by all those who understand English nomenclature.
H . Oettel
[NB 634 IE]
Ylid Chemistry. By A . W. Johnson. Organic Chemistry, Vol. 7.
Academic Press, Inc., New York London 1966. 1st Edit.,
x, 388 pages, numerous figures, bound S 12.50.
The Tower of Pisa leans because the ground subsided while
it was being built. Similarly, the structure of organic chemistry, which is built on the three pillars of carbonium-ion
chemistry, free-radical chemistry, and carbanion chemistry,
cannot be regarded as safe so long as the last of the three
pillars is weaker than the other two. This weakness is obvious from textbooks of organic chemistry.
To learn about the theoretical and practical importance of
carbanion chemistry, one must turn to special books. A new
addition to the ranks of such books is the present work o n
ylid chemistry by A. W. Johnson, who is himself a successful
investigator in this field, and has presented a comprehensive
picture of its development and its present state.
The author condehtrates o n the phosphorus ylids, which
have been. and still me. int,ensite]y studied because of their
preparative importance The bonding in these compounds,
which are formed by removal of a n a proton atom the phosphonium cation (onium complex), 1s eriticzfiy examined o n
the basis of their physical properties and reactivities. Further
chapters are devoted to the olefination ofcarbonyl compounds
and to the iminophosphoranes. This is followed by a discuss-
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