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Book Review Monosaccharides. Their Chemistry and their Roles in Natural Products. By P. M. Collins and R. J. Ferrier

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BOOKS
chapters and a well-prepared index, while
for the scientist already working in solid
state kinetics it is likely to become the
standard work of reference.
Dirk Wilmer
Institut fur Physikalische Chemie
der Universitlt Munster (Germany)
Monosaccharides. Their Chemistry
and their Roles in Natural Products.
By P.M . Collins and R. J. Ferrier.
Wiley, Chichester, 1995. 574 pp., paperback & 22.50.-ISBN
0-47195343-1
The forerunner of this book was published by Penguin Books Ltd. (Harmondsworth, Gre2t Britain) under the title Monosaccharide Chemistry. After a
long interval the authors have now
brought out this up-to-date monograph
on the chemistry of monosaccharides, enlarged to include the whole area of carbohydrates. It is not intended solely for specialists in the field of monosaccharides,
but is designed to have a broader appeal
to everyone concerned with organic chemistry. Thus, the authors rightly point out
that “parts of the book can be looked on
as portrayals of modern general organic
chemistry with monosaccharides as model
systems”. To support this they describe
the development of carbohydrates chemistry since the 1970s, to which not only
carbohydrates chemists but also “mainstream organic chemists” have made fundamental contributions.
A short introduction, in which the
authors discuss the contributions made
by E. Fischer, Haworth, Hudson and
Lemieux to carbohydrates chemistry, is
followed by a second chapter of SO pages
dealing with the structural aspects of
monosaccharides and their biosynthesis.
Although this is intended primarily for
chemists about to begin serious work in
Angew. Chem. Int. Ed. End. 1996,35,No. 8
the field for the first time, it also serves as
a useful “refresher course” for those already experienced in carbohydrates chemistry. Chapter 3 then discusses the reactions occurring at the anomeric center of
aldoses and ketoses, subdivided into the
reactions of free sugars, glycosyl esters,
and 0-protected glycosyl halides. Chapter 4 is concerned with reactions at nonanomeric carbon atoms, beginning with
nucleophilic substitutions and ring-opening reactions of oxiranes, followed by
the synthesis and reactions of deoxy-,
aminodeoxy-, thio-, and deoxyhalogensugars. This chapter also covers the chemistry of anhydro-sugars, ring contractions
of monosaccharides, branched sugars, dicarbonyl compounds and unsaturated
sugars (glycals, 6-deoxy-5-enopyranoses,
and “isolated alkenes”, i.e. monosaccharides with double bonds at other positions). Chapter 5 is concerned with reactions of the hydroxy groups and the
resulting products. First the different reactive properties of the anomeric, primary, and secondary O H groups are described. Other topics discussed here are
the kinetic anomeric effect and the selective substitution of hydroxy groups using
organotin compounds. The reaction
products are classified as ethers, esters
(with sub-sections on enzymatic acylation
and deacylation reactions, orthoesters,
carbonates and their derivatives, sulfonates, chlorosulfonates, sulfites, phosphates, nitrates, borates, boronates, and
borinates), and acetals. This chapter ends
with a detailed discussion of glycol cleavage. Two chapters cover topics that one
would perhaps not expect from the book’s
title. Chapter 6 deals with the synthesis,
structures, and biological functions of
oligosaccharides. These are then considered from a different standpoint in Chapter 8 on natural products, which also
covers polysaccharides, glycoproteins,
proteoglycans, glycolipids, other gly-
Q VCH Verlog.r~e.rell,rchuft
mhH, D-6945i Weinheim, 1996
cosides (including also nucleosides and
their analogs together with nucleotides
and nucleic acids), and cyclitols. Chapter 7 describes syntheses of enantiomerically pure “non-carbohydrates” from
monosaccharides, with some well-chosen
examples (methods using carbohydrates
as chiral auxiliaries, and conversion of
carbohydrates into other products). The
appendix includes a concise survey of the
literature on monosaccharides and a very
brief note on nomenclature rules, referring to D. Horton’s Tentative Rules for
Carbohydrate Nomenclature, Part I, originally published in 1969 and now superseded by a revised edition (1995). Also
included here is a list of trivial names of
sugar derivatives, mainly of microbiological origin, and some ‘H and I 3 C N M R
data for monosaccharides and their peracetates.
Notable features of the book are the
detailed discussions of reaction mechanisms (that of the Ferrier reaction provides
a fitting illustration for the dust-cover)
and of the unique aspects of the reactions
of monosaccharides that result from their
structures. In their presentation of structural formulas the authors have unfortunately been more concerned with “economy” than with esthetic quality. Also they
have been very sparing in mentioning researchers’ names in the text; for example,
in Chapter 6.6 on the synthesis of
oligosaccharides one would at least have
expected a mention of H. Paulsen. This
very convenient book contains over a
thousand literature citations extending up
to 1993, and although these unfortunately
do not include authors’ names they ensure
that it is a valuable reference source. Because of the excellent layout and reasonable price it can also be thoroughly recommended as a student textbook.
Klaus Peseke
Fachbereich Chemie
der Universitlt Rostock (Germany)
0570-0833/96/3508-0915 $15.00+ .25/0
91 S
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