Chemical Education Today
Book & Media Reviews Oligosaccharides: Their Synthesis and Biological Roles by Helen Osborn and Tariq Khan Oxford University Press: New York, 2000. 112 pp. Cloth: ISBN 0-19-850265-6. $65.00. Paper: ISBN 0-19-850260-5. $34.95. reviewed by Michael C. Shelton
In recent years carbohydrate chemistry has moved out of the shadows and taken a prominent place at the interface between chemistry and biology. Carbohydrates, long recognized for their roles in food and nutritional applications, have been found to play prominent roles in a number of physiological processes and diseases, including inflammation process, cancer cell metastasis, reproduction, diabetes, and autoimmune deficiency diseases. The authors, Helen Osborn and Tariq Khan, have written a concise introduction to the field of carbohydrate chemistry. Though titled Oligosaccharides: Their Synthesis and Biological Roles, the book focuses heavily on the synthesis of oligosaccharides and the complex issues that are regularly addressed during the preparation of these molecules. Following a brief introduction to carbohydrate chemistry nomenclature that brings those new to carbohydrates up to speed, only a single chapter is devoted to the biological roles of oligosaccharides. The true value of this book is the synthetic chemistry aspect. The book effectively introduces both undergraduate and graduate students to synthetic carbohydrate chemistry. Protecting-group strategies and glycosylation strategies are
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discussed in detail and the reader leaves with an understanding of the importance of transformations in the preparation of glycosyl acceptors and glycosyl donors. The reader is also introduced to several important concepts in oligosaccharide synthesis, such as neighboring group participation and “armed” and “disarmed” glycosyl donors. The authors introduce the most practiced forms of glycosyl donors, including glycosyl halides, thio ethers, trichloroacetimidates, n-pentenyl glycosides, sulfoxides, and glycals. A series of literature examples of oligosaccharide synthesis are presented and each synthesis is briefly discussed so the reader is made aware of the practical application of the strategies learned in the earlier portions of the book. The last chapter provides accounts of alternate strategies for the synthesis of oligosaccharides that include enzymatic transformations and solid-phase syntheses. Overall this book provides an excellent introduction to the field of oligosaccharide synthesis. Through a series of references, the authors not only introduce the reader to the technical aspects of carbohydrate chemistry, but also to many of the key contributors to the field. Students can quickly build a rather broad base of knowledge of synthetic carbohydrate chemistry by reading this book. I highly recommend this book for use in upper-level undergraduate courses and as a supplement to graduate-level organic synthesis courses. The authors provide an excellent introduction to carbohydrate chemistry and also leave the door open for further investigation by the student. Michael C. Shelton is in Cellulose Esters Technology at Eastman Chemical Company, Kingsport, TN 37662;
[email protected].
Journal of Chemical Education • Vol. 79 No. 5 May 2002 • JChemEd.chem.wisc.edu
