Glycochemical Synthesis

This book is a comprehensive and concise review on principles, strategies, and crucial advances in glycochemistry. It focuses on synthesis and practical applications and emphasizes state-of-the-art approaches to the assembly and design of sugars. • Provides detailed discussion on specific topics like oligosaccharide assembly and design of sugars, techniques in glycoconjugate preparation, multivalency, and carbohydrate-based drug design • Uses notable examples, like solution-based one-pot methods and automated methods for sugar assembly, to illustrate important concepts and advances in a rapidly emerging field • Discusses practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development

This book is a comprehensive and concise review on principles, strategies, and crucial advances in glycochemistry. It focuses on synthesis and practical applications and emphasizes state-of-the-art approaches to the assembly and design of sugars. • Provides detailed discussion on specific topics like oligosaccharide assembly and design of sugars, techniques in glycoconjugate preparation, multivalency, and carbohydrate-based drug design • Uses notable examples, like solution-based one-pot methods and automated methods for sugar assembly, to illustrate important concepts and advances in a rapidly emerging field • Discusses practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development

US, Canadian, and Chinese chemists summarize recent research into the synthesis, principles, and applications of carbohydrates for graduate students and researchers in carbohydrate chemistry, biochemistry, medicinal chemistry, and glycobiology. The topics include solid phase oligosaccharide synthesis, the chemical synthesis of bioactive steroidal saponins, the chemistry and biology of multi-valent saccharide displays, structures and mechanisms of action of aminoglycoside antibiotics, synthesizing glycosaminoglycans, glycosyltransferases in oligosaccharide synthesis, and metabolic substrate engineering as a tool for glycobiology Glycochemistry: Principles, Synthesis, and Applications presents methods used in the development of carbohydrate-based therapeutics. It highlights applications in chemical and enzymatic synthesis of complex carbohydrates, carbohydrate function, and carbohydrate-mediated biological recognition processes. There are practical examples on the development of carbohydrate-based pharmaceuticals and polymers for commercial use. The text also emphasizes the role of carbohydrates as key elements in modern molecular recognition processes.

Synthetic Strategies in Carbohydrate Chemistry covers carbohydrate synthesis and its widespread application in various disciplines including catalysis. Basic and advanced aspects of carbohydrates are covered, starting with a brief introduction and then followed by protection-deprotection strategies in carbohydrate chemistry, glycosidic bond formation methodology, and their impact in oligosaccharide synthesis. Recent synthetic approaches for O-glycosides, N-glycosides, thioglycosides and C-glycosides, Intramolecular Aglycon Delivery (IAD), and carbohydrate modification are discussed, as well as stereoelectronic factors that control the chemical and biochemical behavior of carbohydrates in living cells. In addition, diverse applications of synthetic carbohydrate chemistry are covered, including sugar-based chiral catalyst in stereoselective synthesis, sugar-based ionic liquids, one-pot tandem reactions in carbohydrates, total synthesis of glycoconjugated natural products, impact of sugar in drug discovery and development, vaccine development, and glycoengineering. This reference is essential reading for researchers working in synthetic carbohydrate chemistry and biochemistry, and will be useful to those working in total synthesis, novel synthetic methodology, catalysis, polymer science, glycobiology, medicinal chemistry, and process development chemistry. Presents a practical and detailed overview on glycosylation methodology Covers automated glycosylation strategies in glycan synthesis Includes recent progress in the synthesis and significance of diverse thio-glycosides, C-glycosides, imino sugars and carbasugars Highlights the impact of enzymes in glycan synthesis Discusses the recent approaches for the synthesis of neoglycoconjugates

A unique overview of the most important protecting group strategies in carbohydrate chemistry Protecting Groups: Strategies and Applications in Carbohydrate Chemistry provides a detailed account of key strategies and methodologies for the protection of carbohydrates. Divided into two parts, the first focuses on groups that are used best to protect a specific position on a carbohydrate. In the second part, specific carbohydrate residues or compounds are discussed in the context of a specific protecting group strategy used to reach the desired regioisomer. This important book: -Features chapters on protecting groups at the primary and secondary positions of carbohydrates -Describes protecting group strategies towards sialic acid derivatives, glycofuranoses, sulfated glycosaminoglycans, and cyclodextrins -Provides information on automated glycan assembly -Includes a chapter on the industrial scale synthesis of heparin analogs Written by a team of leaders in the field, Protecting Groups: Strategies and Applications in Carbohydrate Chemistry is an indispensable guide for academics and industrial researchers interested in carbohydrate and natural product synthesis, pharmaceutical chemistry, and biochemistry.

Glycosphingolipids in the Central Nervous System: Diversity in Structure, Metabolism, Distribution, and Function comprehensively covers progress made in the discovery, profiling and understanding of the metabolism, function and functional mechanism of GSLs in the CNS –as well as their synthesis, relationships with and therapeutic applications to neurodegenerative disorders, and related CNS diseases. Due to the important roles of GSLs in the CNS and various CNS-related diseases, the interest in these biomolecules is growing. GSLs are the principal glycolipids on the cell surface and an essential constituent of the cell membrane. They are widespread, but especially enriched in the central nervous system (CNS) in vertebrates. The diversity of GSL structures forges the molecular foundation for their broad spectrum of activity. Presents a systematic review of literature and potential future developments in Glycosphingolipid research Highlights interdisciplinary interplay between various aspects of the neuronal system and its structural and functional properties Provides an overview, general trends, cases studies, summaries and future implications

This book contains original papers and reviews on carbohydrate research in medicine, authored by participants of the 29th International Carbohydrate Symposium, where this topic had a special emphasis. The focus on biological events involving carbohydrates and glycoconjugates has delivered reliable approaches for disease treatment and diagnosis. Research on carbohydrate-based compounds for therapeutic applications is illustrated in various contributions, namely those covering the development of novel agents against Alzheimer’s disease, e.g. the neuroprotective C-glucosylated flavones and the isonucleoside-based cholinesterase inhibitors. New imino sugar glucosidase inhibitors are also disclosed, a class of compounds with potential for diabetes, Gaucher disease or cancer treatment. Also the development of a useful synthetic method towards multivalent glycoclusters of biomedical interest is here highlighted. The relevance of glycomimetics in drug discovery and the progress on carbohydrates in early diagnosis and cancer treatment are reviewed. Noteworthy is the chitosan-based delivery system for drug oral administration, a new biomaterial-based approach to improve bioavailability. Another study on the conformation of Streptococcus capsular polysaccharide backbones by molecular modelling provides useful information for bacterial immunotherapeutic approaches. All original contributions and reviews clearly demonstrate the potential of glycosciences for innovation in medicinal (glyco)chemistry and pharmaceutical research.

In recent years, there has been a steady increase in the publication of papers on the chemistry, biology, and potential clinical uses of marine glycosides. Indeed, more than half of the papers published in this field are less than a decade old. Glycosides have been isolated from species as diverse as algae, fungi, anthozoans, and echinoderms. Even fish of the genus Pardachirus produce glycosides, which they use as shark repellents.The major interest in these compounds as potential drugs stems from their broad spectrum of biological effects. They have been shown to have antimicrobial, antifungal, anti-inflammatory, immune modulatory, and anticancer effects. The anticancer effects of marine glycosides include cell cycle suppression, the induction of apoptosis, and the inhibition of migration, invasion, and metastasis, as well as antiangiogenesis. Marine glycosides influence membrane permeability and have been shown to influence membrane transport at the molecular level through effects on transport carriers and pumps, as well as effects on ligand-gated and voltage-gated channels. Various marine glycosides have been shown to activate sphingomyelinase and ceramide synthesis, to inhibit topoisomerase activity, receptor tyrosine kinase activity, and multidrug resistance protein activity, and to antagonize eicosanoid receptors.This Special Issue covers the entire scope of marine organism-derived glycosides that are of potential value as pharmaceutical agents or leads. These include, but are not limited to, tetracyclic triterpene glycosides, other triterpene glycosides, steroid glycosides, and glycosides of non-isoprenoid aglycones.