Click Chemistry in Glycoscience : New Developments and Strategies.
Title:
Click Chemistry in Glycoscience : New Developments and Strategies.
Author:
Witczak, Zbigniew J.
ISBN:
9781118526187
Personal Author:
Edition:
1st ed.
Physical Description:
1 online resource (404 pages)
Contents:
CLICK CHEMISTRY IN GLYCOSCIENCE -- CONTENTS -- FOREWORD -- PREFACE -- CONTRIBUTORS -- LIST OF ABBREVIATIONS -- PART I CLICK CHEMISTRY STRATEGIES AND DECOUPLING -- 1 PARADIGM AND ADVANTAGE OF CARBOHYDRATE CLICK CHEMISTRY STRATEGY FOR FUTURE DECOUPLING -- 1.1 INTRODUCTION -- 1.2 COUPLING USING HUISGEN DIPOLAR CYCLOADDITION -- 1.3 COUPLING USING THIOL-ENE COUPLING CLICK CHEMISTRY -- 1.4 PROCESSES WHERE BOTH CuAAC AND TEC CLICK CHEMISTRIES ARE USED -- 1.5 DECOUPLING -- 1.5.1 Enzymatic Cleavage -- 1.5.2 Photocleavage -- 1.5.3 Chemical Cleavage -- 1.6 CONCLUSION -- REFERENCES -- PART II THIO-CLICK CHEMISTRY OF CARBOHYDRATES -- 2 THIO-CLICK CHEMISTRY IN GLYCOSCIENCE: OVERVIEW AND PERSPECTIVES -- 2.1 INTRODUCTION -- 2.2 THIO-BASED CLICK REACTIONS -- 2.3 S-THIODISACCHARIDE SYNTHESIS -- 2.4 SYNTHESIS OF GLYCOSYL THIOLS -- 2.5 SYNTHESIS OF S-LINKED GLYCOSPHINGOLIPIDS -- 2.6 CONCLUSION AND PERSPECTIVES -- REFERENCES -- 3 FREE-RADICAL THIOL-ENE AND THIOL-YNE COUPLINGS AS CLICK PROCESSES FOR GLYCOCONJUGATION -- 3.1 INTRODUCTION -- 3.2 S-LINKED OLIGOSACCHARIDES -- 3.3 CALIX[4]ARENE-BASED GLYCOCLUSTERS -- 3.4 SILSESQUIOXANE-BASED GLYCOCLUSTERS -- 3.5 GLYCODENDRIMERS -- 3.6 AMINO ACID, PEPTIDE, AND PROTEIN GLYCOCONJUGATES -- 3.7 CONCLUSION -- REFERENCES -- PART III CARBOHYDRATE CLICK CHEMISTRY FOR NOVEL SYNTHETIC TARGETS -- 4 THE DEVELOPMENT AND APPLICATION OF CLICKABLE LIPID ANALOGS FOR ELUCIDATING AND HARNESSING LIPID FUNCTIONS -- 4.1 INTRODUCTION TO THE ADVANTAGES OF APPLYING CLICK CHEMISTRY FOR STUDYING LIPIDS -- 4.2 APPLICATION OF CLICK CHEMISTRY FOR THE FUNCTIONALIZATION OF MEMBRANE SURFACES -- 4.3 CLICK CHEMISTRY AND THE GENERATION OF FUNCTIONALIZED LIPID ANALOGS -- 4.4 DIRECT IN SITU LABELING AND IMAGING OF SYNTHETICALLY TAGGED LIPID ANALOGS -- 4.5 ACTIVITY-BASED CHARACTERIZATION OF LIPID-BINDING AND LIPID-MODIFYING PROTEINS.
4.6 PROBING COVALENT PROTEIN LIPIDATION -- 4.7 CONCLUSION -- REFERENCES -- 5 CLICKING SUGARS ONTO SUGARS: OLIGOSACCHARIDE ANALOGS AND GLYCOCLUSTERS ON CARBOHYDRATE SCAFFOLDS -- 5.1 INTRODUCTION -- 5.2 TRIAZOLE-LINKED OLIGOSACCHARIDE ANALOGS -- 5.3 CLICKED CYCLODEXTRINS -- 5.4 TRIAZOLE-LINKED MACROCYCLES -- 5.5 MULTIVALENT GLYCOCLUSTERS ON CARBOHYDRATE SCAFFOLDS -- 5.6 CONCLUSION -- REFERENCES -- 6 CLICK MULTIVALENT GLYCOMATERIALS: GLYCOCLUSTERS, GLYCODENDRIMERS, GLYCOPOLYMERS, HYBRID GLYCOMATERIALS, AND GLYCOSURFACES -- 6.1 INTRODUCTION -- 6.2 CLICK GLYCOCLUSTERS -- 6.3 CLICK GLYCODENDRIMERS -- 6.4 CLICK GLYCOPOLYMERS -- 6.5 CLICK HYBRID GLYCOMATERIALS -- 6.6 CLICK GLYCOSURFACES AND GLYCOARRAYS -- 6.7 CLICK MULTIVALENT GLYCOMIMETICS -- REFERENCES -- 7 TOWARD IMAGING GLYCOTOOLS BY CLICK COUPLING -- 7.1 INTRODUCTION -- 7.2 NUCLEAR IMAGING AND RADIOTRACERS -- 7.3 TRIAZOLE-CONTAINING RADIOTRACERS -- 7.3.1 Conjugation of Labeled Carbohydrates -- 7.3.2 Glycoconjugation of Radiotracers -- 7.3.3 Carbohydrate Labeling -- 7.4 OTHER METHODS -- 7.4.1 Maillard Reaction -- 7.4.2 Oxime Formation -- 7.4.3 Glycosylation -- 7.4.4 Disulfide Formation -- 7.5 CONCLUSION AND OUTLOOK -- REFERENCES -- 8 BIOORTHOGONAL REACTIONS FOR LABELING GLYCOCONJUGATES -- 8.1 INTRODUCTION -- 8.2 KETONE-BASED BIOORTHOGONAL LABELING OF GLYCOCONJUGATES -- 8.3 AZIDO- AND ALKYNE-BASED STRATEGIES FOR BIOORTHOGONAL LABELING OF GLYCOCONJUGATES -- 8.4 STAUDINGER LIGATION -- 8.5 CuI-CATALYZED AZIDE-ALKYNE CYCLOADDITIONS (CuAAC) -- 8.6 STRAIN PROMOTED AZIDE-ALKYNE CYCLOADDITIONS (SPAAC) -- 8.7 STRAIN-PROMOTED CYCLOADDITIONS WITH NITRONES, NITRILE OXIDES, AND DIAZOCARBONYL DERIVATIVES -- 8.8 METABOLIC LABELING WITH PHOTOACTIVATABLE CROSSLINKING SUGARS -- 8.9 METABOLIC LABELING WITH THIOL-CONTAINING SUGARS -- 8.10 CONCLUDING REMARKS -- REFERENCES.
9 "SWEET" SUCROSE MACROCYCLES VIA A "CLICK CHEMISTRY" ROUTE -- 9.1 INTRODUCTION -- 9.2 CONCLUSION -- ACKNOWLEDGMENT -- REFERENCES -- PART IV CARBOHYDRATE CLICK CHEMISTRY IN BIOMEDICAL SCIENCES -- 10 NEOGLYCOPROTEIN SYNTHESIS USING THE COPPER-CATALYZED AZIDE-ALKYNE CLICK REACTION AND NATIVE CHEMICAL LIGATION -- 10.1 INTRODUCTION -- 10.2 STRATEGIES FOR THE SYNTHESIS OF NEOGLYCOPEPTIDES AS GLYCOPEPTIDE MIMETICS -- 10.3 SYNTHESIS OF NEOGLYCOPEPTIDE MIMICS OF FISH ANTIFREEZE GLYCOPEPTIDES -- 10.3.1 Combining Azido Peptides with Alkynyl Sugars -- 10.4 SYNTHESIS OF NEOGLYCOPEPTIDE MIMICS OF THE MUCINS -- 10.4.1 Combining Alkynyl Peptides and Azido Sugars -- 10.5 APPLICATION OF NCL TO THE SYNTHESIS OF NEOGLYCOPEPTIDES -- 10.5.1 A One-Pot Approach -- 10.6 LARGE COMPLEX NEOGLYCOPROTEINS -- 10.6.1 Combining Click Chemistry with NCL for the de novo Synthesis of Large Neoglycoprotein Constructs -- 10.7 CONCLUSION -- REFERENCES -- 11 BIOMEDICAL APPLICATIONS OF "CLICK"-MODIFIED CYCLODEXTRINS -- 11.1 INTRODUCTION -- 11.2 CHEMICAL MODIFICATION OF CYCLODEXTRINS -- 11.3 BIOMEDICAL APPLICATIONS -- 11.3.1 Chiral Separation -- 11.3.2 Functional Biomaterials -- 11.3.3 Biological Sensors -- 11.3.4 Drug Delivery -- 11.4 SUMMARY -- ACKNOWLEDGMENT -- REFERENCES -- 12 TRIAZOLYL GLYCOCONJUGATES IN MEDICINAL CHEMISTRY -- 12.1 INTRODUCTION -- 12.2 Cu(I)-CATALYZED ALKYNE-AZIDE CYCLOADDITION (CuAAC) REACTION -- 12.3 MECHANISM OF Cu-CATALYZED CLICK REACTION -- 12.4 TRIAZOLE RING AS BIOISOSTERES OF AMIDE -- 12.5 TRIAZOLYL GLYCOCONJUGATES IN MEDICINAL CHEMISTRY -- 12.5.1 Anticancer and Anti-Inflammatory Activities -- 12.5.2 Antituberculosis Agent -- 12.5.3 Antifungal and Antibacterial -- 12.5.4 Antiviral Activities -- 12.5.5 Miscellaneous Activities -- 12.6 CONCLUSION AND FUTURE PERSPECTIVE -- ACKNOWLEDGMENT -- REFERENCES.
13 CLICK CHEMISTRY APPLIED TO CARBOHYDRATE-BASED DRUG DISCOVERY -- 13.1 INTRODUCTION -- 13.2 CLICK CHEMISTRY AND CARBOHYDRATE-BASED LIGANDS FOR LECTINS (GALECTINS AND SELECTINS) -- 13.2.1 Galectins -- 13.2.2 Selectins -- 13.3 CLICK CHEMISTRY AND GLYCOCONJUGATE ANTITUMOR VACCINES -- 13.4 CLICK CHEMISTRY AND CARBOHYDRATE-BASED ENZYME INHIBITORS -- 13.4.1 Fucosyltransferases (Fuc-T) -- 13.4.2 Mannosyltransferases -- 13.4.3 Glucosidases -- 13.4.4 Neuraminidase -- 13.4.5 Trypanosoma cruzi Trans-Sialidase -- REFERENCES -- INDEX -- Supplemental Images.
Abstract:
Lays the foundation for new methods and applications of carbohydrate click chemistry Introduced by K. Barry Sharpless of The Scripps Research Institute in 2001, click chemistry mimics nature, giving researchers the tools needed to generate new substances quickly and reliably by joining small units together. With contributions from more than thirty pioneering researchers in the field, this text explores the many promising applications of click chemistry in glycoscience. Readers will learn both the basic concepts of carbohydrate click chemistry as well as its many biomedical applications, including synthetic antigens, analogs of cell-surface receptors, immobilized enzymes, targeted drug delivery systems, and multivalent cancer vaccines. Click Chemistry in Glycoscience examines a broad range of methodologies and strategies that have emerged from this rapidly evolving field. Each chapter describes new approaches, ideas, consequences, and applications resulting from the introduction of click processes. Divided into four sections, the book covers: Click chemistry strategies and decoupling Thio-click chemistry of carbohydrates Carbohydrate click chemistry for novel synthetic targets Carbohydrate click chemistry in biomedical sciences Thoroughly researched, the book reflects the most recent findings published in the literature. Diagrams and figures throughout the book enable readers to more easily grasp complex concepts and reaction processes. At the end of each chapter, references lead to the primary literature for further investigation of individual topics. The application of click chemistry to carbohydrates has tremendous implications for research. With this book as their guide, researchers have a solid foundation from which they can develop new methods and applications of carbohydrate click chemistry, including new carbohydrate-based therapeutics.
Local Note:
Electronic reproduction. Ann Arbor, Michigan : ProQuest Ebook Central, 2017. Available via World Wide Web. Access may be limited to ProQuest Ebook Central affiliated libraries.
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