PREFACE Many recent volumes in this series have been strongly oriented toward biochemical or medicinal chemical aspects. This current volume focuses on basic chemical aspects of mono- and oligo-saccharides, and on polysaccharide technology. de Lederkremer and Gallo-Rodriguez (Buenos Aires) provide a comprehensive survey of those monosaccharides (excluding amino and deoxy sugars) that are found in natural products, in a treatment that greatly extends a 1972 treatment of this subject by Schaffer. The chapter by Garegg (Stockholm) presents a broad overview of the chemistry of glycosides, dealing with their synthesis, structure, and properties. It places particular emphasis on the ongoing challenge of glycoside synthesis as it applies to complex oligosaccharide targets, and it features much of the author’s own considerable contribution to this area. The inositols and their derivatives can be regarded as monosaccharide sugars in which the ring oxygen atom has been replaced by carbon, and they may thus be named as carba sugars. The inososes derived by their oxidation react with hydrazines in transformations that are often of considerable complexity, thus resembling the behavior of sugars. The hydrazine derivatives of sugars have been surveyed in detail in this Series by El Khadem in Volume 20 and again in conjunction with Fatiadi in Volume 55. In this volume El Khadem and Fatiadi (Washington, DC) complement this aspect with a comprehensive account of the hydrazine derivatives of carba sugars. The technology of polymeric carbohydrates is strongly oriented to the most abundant examples, namely starch and cellulose. Tomasik (Cracow) and Schilling (University Center, Michigan), in their wide-ranging article on chemical derivatization of starch, present an extensive compilation of the literature on potentially useful products formed by esterification, etherification, oxidation, and other reactions with starch. Much of the literature cited comes from patent sources, not subject to the conventional refereeing procedures in effect for journal articles, and so the reader needs to judge appropriately the validity of some of the claims made for product structure and practical application. The life and work of Edward J. Hehre, a pioneer in our knowledge of the mechanism of action of glycosylase enzymes, is the subject of the article by Brewer (New York). It is noted with regret the passing on February 23, 2004, of Aleskander Zamojski, who contributed in Volume 40 an article on the synthesis of sugars from noncarbohydrate sources, and on July 31, 2004, of Jacques van Boom (Leiden), who made important contributions to carbohydrate synthesis and to glycobiology. ix

[Advances in Carbohydrate Chemistry and Biochemistry] Advances in Carbohydrate Chemistry and Biochemistry Volume 59 Volume 59 || PREFACE

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PREFACE

Many recent volumes in this series have been strongly oriented toward biochemicalor medicinal chemical aspects. This current volume focuses on basic chemicalaspects of mono- and oligo-saccharides, and on polysaccharide technology.de Lederkremer and Gallo-Rodriguez (Buenos Aires) provide a comprehensivesurvey of those monosaccharides (excluding amino and deoxy sugars) that arefound in natural products, in a treatment that greatly extends a 1972 treatmentof this subject by Schaffer. The chapter by Garegg (Stockholm) presents a broadoverview of the chemistry of glycosides, dealing with their synthesis, structure,and properties. It places particular emphasis on the ongoing challenge of glycosidesynthesis as it applies to complex oligosaccharide targets, and it features much ofthe author’s own considerable contribution to this area.

The inositols and their derivatives can be regarded as monosaccharide sugars inwhich the ring oxygen atom has been replaced by carbon, and they may thus benamed as carba sugars. The inososes derived by their oxidation react with hydrazinesin transformations that are often of considerable complexity, thus resembling thebehavior of sugars. The hydrazine derivatives of sugars have been surveyed in detailin this Series by El Khadem in Volume 20 and again in conjunction with Fatiadi inVolume 55. In this volume El Khadem and Fatiadi (Washington, DC) complementthis aspect with a comprehensive account of the hydrazine derivatives of carbasugars.

The technology of polymeric carbohydrates is strongly oriented to themost abundant examples, namely starch and cellulose. Tomasik (Cracow) andSchilling (University Center, Michigan), in their wide-ranging article on chemicalderivatization of starch, present an extensive compilation of the literature onpotentially useful products formed by esterification, etherification, oxidation, andother reactions with starch. Much of the literature cited comes from patent sources,not subject to the conventional refereeing procedures in effect for journal articles,and so the reader needs to judge appropriately the validity of some of the claimsmade for product structure and practical application.

The life and work of Edward J. Hehre, a pioneer in our knowledge of themechanism of action of glycosylase enzymes, is the subject of the article byBrewer (New York). It is noted with regret the passing on February 23, 2004, ofAleskander Zamojski, who contributed in Volume 40 an article on the synthesis ofsugars from noncarbohydrate sources, and on July 31, 2004, of Jacques van Boom(Leiden), who made important contributions to carbohydrate synthesis and toglycobiology.

Page 2: [Advances in Carbohydrate Chemistry and Biochemistry] Advances in Carbohydrate Chemistry and Biochemistry Volume 59 Volume 59 || PREFACE

x preface

With this volume we thank two members of the Board of Advisors, Roy L.Whistler and Bengt Lindberg, for their long service to the series, and welcomeGeert-Jan Boons and Serge Perez to the Board.

Derek HortonWashington, DCSeptember 2004