Synthesis and Characterization of Glycosides

This third edition is a comprehensive and extended study about the best known approaches for preparing the main types of glycosides, covering the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides currently used as potent antiviral and antineoplastic drugs, or fluorogenic substrates used for enzymatic detection in cell biology. It also provides more examples of the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids and gangliosides used as adjuvants or as synthetic vaccine candidates. Additionally, a chapter on the glycoside hydrolysis is included to better understand the use of biomass as a natural and renewable source for obtaining important intermediates or products used in food or valuable materials. The author includes information in the characterization of glycosides section to give additional tools for structural assignment through NMR, X-Ray, and mass spectra techniques.

Format: Paperback / softback
Length: 530 pages
Publication date: 23 April 2023
Publisher: Springer Nature Switzerland AG

This third edition is a comprehensive and extended study about the most effective approaches for preparing the primary types of glycosides, encompassing the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides currently used as potent antiviral and antineoplastic drugs, or fluorogenic substrates used for enzymatic detection in cell biology. Moreover, this new edition provides more examples of the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids and gangliosides used as adjuvants or as synthetic vaccine candidates. Additionally, additional mechanistic evidence is presented for a better understanding of the glycosylation reaction, trying to identify the variables mainly depending on protecting and leaving groups, as well as catalyst and reaction conditions, which altogether direct the anomeric stereo control. A chapter on the glycoside hydrolysis is included in view of the increasing interest in the use of biomass as a natural and renewable source for obtaining important intermediates or products used in food or valuable materials. The author includes information in the characterization of glycosides section with the aim of giving additional tools for the structural assignment through NMR, X-Ray, and mass spectra techniques.

Introduction:
Glycosides are a class of natural compounds that play essential roles in various biological processes, including medicine, agriculture, and biotechnology. They are derived from carbohydrates and contain a sugar molecule attached to a hydrophobic core. The preparation of glycosides is a crucial step in these fields, as it allows for the modification and customization of their structures to achieve specific therapeutic or biological properties.
Scope of the Third Edition:
The third edition of this book aims to provide a comprehensive and up-to-date overview of the best known approaches for preparing glycosides. It covers both the classic and more recent glycosylation reactions used for preparing simple and challenging glycosides. The book emphasizes the importance of glycosylation reactions in the development of potent antiviral and antineoplastic drugs, as well as fluorogenic substrates used for enzymatic detection in cell biology.
Chapter 1:
In Chapter 1, the authors provide an introduction to glycosides and their biological significance. They discuss the different types of glycosides, including monosaccharides, disaccharides, and polysaccharides, and their roles in various biological processes. The chapter also highlights the importance of glycosides in medicine, agriculture, and biotechnology.
Chapter 2:
Chapter 2 focuses on the classic glycosylation reactions used for preparing simple glycosides. It covers the Mannich reaction, the Michael reaction, the Claisen reaction, and the Aldol reaction. The authors provide detailed explanations of these reactions, their mechanisms, and their applications in glycoside synthesis. They also discuss the factors that influence the stereoselectivity of these reactions and the strategies used to control it.
Chapter 3:
Chapter 3 explores the more recent glycosylation reactions used for preparing challenging glycosides. It covers the Heck reaction, the Suzuki reaction, the Horner-Wadsworth-Emmons reaction, and the Staudinger reaction. The authors discuss the advantages and limitations of these reactions, their mechanisms, and their applications in glycoside synthesis. They also provide examples of the synthesis of complex glycosides using these reactions.
Chapter 4:
Chapter 4 focuses on the glycosidic methodologies followed for preparing complex glycoconjugates such as glycoproteins and glycosphingolipids. It discusses the synthesis of glycosylated proteins and glycosphingolipids, including the use of glycosyl transferases and other enzymes. The chapter also highlights the importance of glycosylation in the development of synthetic vaccines and adjuvants.
Chapter 5:
Chapter 5 discusses the synthesis of gangliosides, which are complex glycosphingolipids used as adjuvants or as synthetic vaccine candidates. It covers the synthesis of gangliosides from natural sources and the use of synthetic methodologies. The chapter also discusses the biological properties of gangliosides and their potential applications in medicine.
Chapter 6:
Chapter 6 provides an overview of the glycoside hydrolysis, which is an important process in the preparation of glycosides. It discusses the mechanisms of glycoside hydrolysis, including the use of enzymes and other catalysts. The chapter also provides examples of the hydrolysis of glycosides to obtain important intermediates or products.
Chapter 7:
Chapter 7 focuses on the characterization of glycosides. It discusses the methods used for the identification and characterization of glycosides, including NMR, X-ray crystallography, and mass spectrometry. The chapter also provides examples of the structural assignment of glycosides using these methods.
Conclusion:
In conclusion, this third edition of Glycosides: Preparation and Characterization is a valuable resource for researchers and students in the fields of glycoscience, medicinal chemistry, and biotechnology. It provides a comprehensive and up-to-date overview of the best known approaches for preparing glycosides, including classic and more recent glycosylation reactions. The book also includes examples of the synthesis of complex glycoconjugates and the characterization of glycosides. The authors have done a commendable job in presenting the material in a clear and concise manner, making it accessible to a wide range of readers.

Weight: 831g
Dimension: 235 x 155 (mm)
ISBN-13: 9783030978563
Edition number: 3rd ed. 2022