[9] X.-M. Chen. Thomas C. W. Mak. Polyhedron 1991. If). 1723. [lo] Malonatodisilver(t) is polymeric too. but its structure is completely differ-

ent to ours: F. Charbonnier. R. Faure. H. Loiseleur. R w Cl7im. Mmer. 1981. 18.245.

[ l l ] A. Michaelides. S. Skoulika. J. Cryst. Growlh 1989. 94, 208. [12] A. Michaelides, S. Skoulika. A. Aubry. Mutiv. Res. BUN. 1988, 23, 579. 1131 The compound is insoluble in all common organic solvents and thermally

stable up to 250 C. [14] Orthorhomhic. u =16.218(3). h =11.919(3). c = t1.778(2) A. V =

-_ 2’74 A’. FO&l. e,,,, = 3.872 gem-', CAD-4 diffractometer. u~j21i scan. graphite-monochroniated Mo,, radiation. SHELXS-86 and SHELX-76 program systems. 740 reflections with I > 3 ~ ( 1 ) . no empirical absorption correction. Anisotropic refinement R = 0.0279. R, = 0.0322. secondary extinction correction. Further details of the crystal structure investigation iii-e available on request from the Director of the Cambridge Crystallo- graphic Data Centre, 12 Union Road. GB-Cambridge CB2 1EZ (UK) , on quoting the full journal citation.

[15] In this respect, this structure is reminiscent of that of[Cd(SPh),]: D. Craig. I. G . Dance, R. Garbutt, Angeir. Chem. 1986, Y8, 178: A n p i . Chrni. Inr. Ed. Engl. 1986, 25, 165.

1161 Interesting examples of interpenetrating diamandoid frameworks are given in a) K. W. Kim. M. G. Kanatzidis. J. Am. Cliem. So<.. 1992. 114. 4878; b) 0 Ermer, ibrd 1988, f10, 3747; c) 0. Ermer, A. Eling. Angeir. Chrm. 1988, 100, 856; Angen. Chrrn. In?. Ed. EngI. 1988.27. 829.

[17] M. Jansen. Angeii-. Ciiem. 1987, Y9. 1136; Angrii , Chlem. h r . Ed. Engi. 1987.26. 1098.

[18] This motif has recently been observed in the structure of the silver com- pound [Ag(F ~ C,H,N,C,H,-F)],: E. Hartmann. J. Strihle. %. A n o , ~ . Allg. Chcm. 1990, 583. 31.

[19] F Charbonnier, R. Faure. M. Petit-Ramel, Eur. J. SolrdSrurr Inory. Chcm. 1992, 29. 93.

[20] Crystals of Ag’ with other dicarboxylic acids have been obtained, and the structures will soon be solved.

[21] E. Keller. SCHAKAL, Universitiit Freiburg (FRG) 1988.

BOOKS

Book Reviews

Human Protein Data. 1st Instalment. Edited by A . Haeberli. VCH Verlagsgesellschaft, Weinheim/VCH Publishers, New York, 1992. XLV, 424 pp., looseleaf collection D M 275.00, subscription price D M 225.00.--ISBN 3- 527-2821 1 -4/1-56081-110-2

To begin compiling a collection of data on human proteins probably strikes most of us as an unending task, comparable with the rapidly growing data banks of protein sequences. It is, therefore, all the more pleasing that three years ago A. Haeberli had the courage to make a start on this, and espe- cially that he had the good sense to delegate much of the work, in which so far 167 authors have covered 147 proteins. Anyone who sees gaps in this and feels a duty to contribute is likely to be enthusiastically recruited by the editor to join in. Thus one can envisage that the necessary continuation and updating of this looseleaf collection, which the publish- ers plan to extend by about 70 more proteins per year, will proceed successfully. The 147 proteins in this first instalment are mainly plasma proteins, together with a number of protein hormones and protein factors. The descriptions are concise, comprehensible to the general user and not too spe-

Angeii . C h m 1171. Ed Engl. 1993, 32, No. 10 t:; VCH ~~rlugsgesells~hufi mhH, D-694Sl Wemheim, 1993 1~S71~-0~33~93~10l0-1497 $ l O . O O + ,2510 1497

cialized, and contain quite enough information for a first source. Relevant literature references enable one to go into more detail.

The same clear layout is used for each protein, listing synonyms, abbreviations, classification, e.g. according to EC number or from serum electrophoresis, short description, structural features, molecular mass, sedimentation constant, isoelectric point, extinction coefficient, enzymic activity, coenzymes/cofactors, substrates, inhibitors, biological func- tion, physiological and pathological role, breakdown behav- ior, genetics and mutants, biological half-life, concentration and isolation procedures, sequence, and disulfide or SH groups. In many cases the structure is illustrated at the end by a clear schematic diagram, or by three-dimensional dia- grams and ribbon models where these are known. The above list is, of course, very comprehensive, and it is not surprising that in many cases not every item of information has yet been included. However, this does not indicate that the searching has been inadequate but rather that an effort has been made to present the very latest knowledge. In view of the brevity of the I D codes of proteins as given in sequence data banks, it would not have been a bad idea to include cross-references to, for example, PIR, SWISSPROT, or the protein structure data bank.

The question arises: why a growing file for our book- shelves rather than a data bank for interrogating through the VDU screen? Ten years from now the answer to this question is likely to be different. At present the proportion of bio- chemists and medical scientists who can gain access to a central external data bank through a computer terminal near their desk, or who wish to learn how to d o so, is probably less than 10%. However, for the VDU enthusiasts among them a diskette is included in the package.

In 1990 the Gesellschaft fur Biotechnologische Forschung (GBF) in Braunschweig issued an “Enzyme Handbook” consisting of five AS-size files, listing enzymes according to their EC numbers. Although the GBF files and the “Human Protein Data” collection reviewed here appear to have simi- lar aims, they are somewhat different in style. Neither makes the other redundant: to begin with, the “Enzyme Hand- book” sets out to cover all the known sources for each en- zyme. It is desirable that the different approaches should be maintained, so that the two works will complement rather than duplicate each other.

The “Human Protein Data” collection will become in- creasingly important as the human genome project gets un- der way. It is only by combining information on the many possible human DNA sequences with a data bank on gene products that advances in practically useful knowledge can be achieved.

Emil Schiltz Institut fur Organische Chemie und Biochemie

der Universitat Freiburg (FRG)

Organic Peroxides. Edited by W Ando. Wiley, Chichester, 1992. XVI, 845 pp., hardcover E 140.00.-ISBN 0-471- 93438-0

Qinghaosu is a naturally occuring tetracyclic peroxide with high anti-malarial activity, and is extracted from Artemisia annua, a plant that is widely distributed in China. An unusual structure might be expected to be associated with unusual properties, and this is confirmed for many per- oxides. This class of compounds has been much studied by chemists since the end of the nineteenth century. In recent decades research activity has further intensified, because per- oxides are in many cases ideal reagents for the synthesis of oxyfunctionalized compounds, they play an essential role in the metabolization of chemicals by organisms, and reactive peroxides often undergo thermal or photochemical break- down through unusual pathways. These different aspects of the subject are drawn together in this excellent book.

The editor, W. Ando. has succeeded in recruiting expert authors for all the chapters, and thereby presenting an overview of this important area of chemistry which is thor- oughly up-to-date (including many literature citations from the last five years). Synthetic routes to the above mentioned compound qinghaosu alone are described in five chapters. However, the overall layout of the book is unimaginative. Thus, the first ten chapters deal with different compound classes, and only in the last five chapters is the subject matter arranged according to oxidation pathways. Consequently, although finding an answer to a question of detail should be relatively quick and straightforward, there has evidently been no attempt to unite the topics in a way that could also introduce non-specialists to the field.

In the first hundred pages Yamaguchi and co-authors give an excellent overview of theoretical aspects of organic perox- ides. Modern views concerning the Sharpless epoxidation are discussed, as also are the studies by Bernardi on the addition of singlet oxygen to ethylene and by Robb on the breakdown of 1,2-dioxetanes (1990, 1991). The chapters on alkyl hydroperoxides (Ch. 2, Porter), dialkyl peroxides (Ch. 3, Matsugo and Saito), diacyl peroxides (Ch. 7, Fuji- mori), sulfur and phosphorus peroxides (Ch. 8, Kim), and peroxyacids and peroxyesters (Ch. 9, Sawaki) are well worth reading and of appropriate length, and give particular atten- tion to the uses of these compounds in synthesis. In cases where chapter subjects have not been clearly defined before- hand, overlapping always results. Thus, under the heading of dialkyl hydroperoxides we find that many endoperoxides and their reactions are treated, then these appear again in the chapter with this title (Ch. 6, Clennan and Foote). Of special interest here are the important studies by Jefford on the synthesis of 1,2,4-trioxanes and by Hayes on copper(I1)- and iron(rr1)-catalyzed cyclizations of alkyl hydroperoxides (both of which are also relevant to the synthesis of qinghaosu and its analogues). Dioxirdnes and dioxetanes are treated very

briefly in Chapters 4 and 5 (Adam et al.). Here one is relieved to find that the authors have avoided giving an encyclopedic list of all the available data on reactions of dioxiranes and properties of dioxetanes, which would be enough to fill an- other book. Dioxirane chemistry is undergoing a near-explo- sive phase of development, as is apparent from the bibliogra- phy, in which half the papers cited are for the period 1989- 1992. In contrast, dioxetane chemistry is relatively quiet, although some interesting transformations of these highly reactive peroxides have recently been discovered. Polyoxides, a class of compounds that chemists tend to group under “exotica”, are described by PlesniEar in Chap- ter 10. The author gives a nice explanation of how these compounds have gradually emerged from being regarded as merely unstable intermediates or models for theoretical stud- ies, and are now even used in synthesis. One of special inter- est is triethylsilylhydrotrioxide (Corey, Posner), which can be used as a source of singlet oxygen, or for the direct (per)oxyfunctionalization of carbon -carbon double bonds or thioethers.

Chapters 11 - 14 are concerned with four methods for the synthesis of peroxides. Modena et al. report on the current state of metal-catalyzed oxidation reactions. However, there is no mention of biochemical processes, and only a very inadequate treatment of applications of the Sharpless and Kagan methods to enantioselective oxidations, cis-hydrox- ylations, and the oxidation of thioethers. The photosensi- tized oxygenation of heteroatoms (Ch. 12, Akasaka and Ando), the ozonolysis method (Ch. 13, McCullogh and No- jima), and reactions using superoxides (Ch. 14, Nagano et al.) yield peroxides with a great variety of structures, and these methods are therefore treated very thoroughly. But here, if not earlier in the book, one notes with annoyance that there is no chapter on the synthesis of peroxides by reactions using singlet oxygen. Whereas a separate chapter is devoted to heteroatom photooxidation reactions (which are the editor’s specialty), photooxidations of alkenes, alkynes, dienes, etc. are only mentioned under the corresponding compound classes, inevitably resulting in incomplete cover- age. There are, of course, alternative publications such as the (now rather outdated) book by Murray (1979), or the CRC collection by Frimer (1 9 8 9 , but this remains a shortcoming in the present work. Lastly, with the aim of making a link with biology, a brief discussion of peroxides in biological systems has been added (Ch. 15, Niki).

Overall this is a very useful collection of articles on the current state of peroxide chemistry, and despite a few gaps in the coverage it deserves to reach a wide readership. Addi- tional points in its favor are the high standard of production and the consistent quality of the figures.

Axel G. Griesbeck Institut fur Organische Chemie

der Universitat Wiirzburg (FRG)

Writing Reaction Mechanisms in Organic Chemistry. By A . Miller. Academic Press, New York, 1992. X, 488 pp., hardcover (spiral binding) $34.95.-ISBN 0-1 2-49671 1-6

The title accurately describes what this book is about: writing equations that represent the “correct” (i.e. most plausible) reaction mechanisms. It is intended mainly for students beginning their first course in organic chemistry; some parts of the chapters on free radicals and pericyclic reactions will also be of interest to more advanced students.

1498 VCH Verlagsgesellschufi mhH, 0-69451 Weinheim, 1993 (~57o-o8331931lo10-,49R $ I0.00+ ,2510 Angyw. C h m . Int. Ed. Engl. 1993, 32. N o . 10