The first text to focus on the application of click chemistry to glycoscience, this book discusses the therapeutic and pharmacological aspects of carbohydrate click chemistry and includes chapters on the concept s background, as well as its industrial applications in areas such as drug discovery. The book reflects the novel methodologies and strategies of this concept. Each chapter describes new approaches, ideas, consequences, and applications deriving from the introduction of click processes. This provides an essential reference for a wide range of researchers and graduate-level students.
The first text to focus on the application of click chemistry to glycoscience, this book discusses the therapeutic and pharmacological aspects of carbohydrate click chemistry and includes chapters on the concept s background, as well as its industrial applications in areas such as drug discovery. The book reflects the novel methodologies and strategies of this concept. Each chapter describes new approaches, ideas, consequences, and applications deriving from the introduction of click processes. This provides an essential reference for a wide range of researchers and graduate-level students.
ZBIGNIEW J. WITCZAK, PhD, is Professor in the Department of Pharmaceutical Sciences of the Nesbitt School of Pharmacy at Wilkes University. He has published over ninety research papers and holds six patents. His research focuses on carbohydrate synthons, including levoglucosenone and L-arabinose, as templates for carbohydrate-based therapeutics. In 2000, Dr. Witczak was awarded the Melville L. Wolfrom Award from the ACS Division of Carbohydrate Chemistry. ROMAN BIELSKI, PhD, is Senior Scientist at Value Recovery, Inc., Partner in Cheminnolab, LLC, and Adjunct Professor in the Department of Pharmaceutical Sciences at Wilkes University. His research investigates the origin of homochirality, modification of carbohydrates, solutions to environmental issues, and sustainability. As part of his achievements, Dr. Bielski co-developed a method of enantiomers' resolution, which might have been involved in prebiotic homochirality, since it would not require the use of chiral compounds.
Inhaltsangabe
FOREWORD vii PREFACE ix CONTRIBUTORS xiii LIST OF ABBREVIATIONS xvii I CLICK CHEMISTRY STRATEGIES AND DECOUPLING 1 Paradigm and Advantage of Carbohydrate Click Chemistry Strategy for Future Decoupling 3 Roman Bielski and Zbigniew J. Witczak II THIO-CLICK CHEMISTRY OF CARBOHYDRATES 2 Thio-Click Chemistry in Glycoscience: Overview and Perspectives 33 Zbigniew J. Witczak 3 Free-Radical Thiol-ene and Thiol-yne Couplings as Click Processes for Glycoconjugation 45 Alessandro Dondoni and Alberto Marra III CARBOHYDRATE CLICK CHEMISTRY FOR NOVEL SYNTHETIC TARGETS 4 The Development and Application of Clickable Lipid Analogs for Elucidating and Harnessing Lipid Functions 79 Michael D. Best 5 Clicking Sugars onto Sugars: Oligosaccharide Analogs and Glycoclusters on Carbohydrate Scaffolds 107 Maria Laura Uhrig and Jos e Kovensky 6 Click Multivalent Glycomaterials: Glycoclusters, Glycodendrimers, Glycopolymers, Hybrid Glycomaterials, and Glycosurfaces 143 Carmen Ortiz Mellet, Alejandro M endez-Ardoy, and Jos e Manuel Garc (c)¥a Fern andez 7 Toward Imaging Glycotools by Click Coupling 183 Yves Chapleur, Christine Vala, Franc oise Chr etien, and Sandrine Lamand e-Langle 8 Bioorthogonal Reactions for Labeling Glycoconjugates 211 Fr ed eric Friscourt and Geert-Jan Boons 9 "Sweet" Sucrose Macrocycles via a "Click Chemistry" Route 235 Mykhaylo A. Potopnyk and S(c)(c)awomir Jarosz IV CARBOHYDRATE CLICK CHEMISTRY IN BIOMEDICAL SCIENCES 10 Neoglycoprotein Synthesis Using the Copper-Catalyzed Azide-Alkyne Click Reaction and Native Chemical Ligation 253 Joanna M. Wojnar, Dong Jun Lee, Clive W. Evans, Kalyaneswar Mandal, Stephen B. H. Kent, and Margaret A. Brimble 11 Biomedical Applications of "Click"-Modified Cyclodextrins 271 Zhenshan Jia, Rakesh K. Singh, and Dong Wang 12 Triazolyl Glycoconjugates in Medicinal Chemistry 293 Rama Pati Tripathi, Pratibha Dwivedi, Anindra Sharma, Divya Kushwaha, and Vinod Kumar Tiwari 13 Click Chemistry Applied to Carbohydrate-Based Drug Discovery 325 Vanessa Leiria Campo and Ivone Carvalho INDEX 359
FOREWORD vii PREFACE ix CONTRIBUTORS xiii LIST OF ABBREVIATIONS xvii I CLICK CHEMISTRY STRATEGIES AND DECOUPLING 1 Paradigm and Advantage of Carbohydrate Click Chemistry Strategy for Future Decoupling 3 Roman Bielski and Zbigniew J. Witczak II THIO-CLICK CHEMISTRY OF CARBOHYDRATES 2 Thio-Click Chemistry in Glycoscience: Overview and Perspectives 33 Zbigniew J. Witczak 3 Free-Radical Thiol-ene and Thiol-yne Couplings as Click Processes for Glycoconjugation 45 Alessandro Dondoni and Alberto Marra III CARBOHYDRATE CLICK CHEMISTRY FOR NOVEL SYNTHETIC TARGETS 4 The Development and Application of Clickable Lipid Analogs for Elucidating and Harnessing Lipid Functions 79 Michael D. Best 5 Clicking Sugars onto Sugars: Oligosaccharide Analogs and Glycoclusters on Carbohydrate Scaffolds 107 Maria Laura Uhrig and Jos e Kovensky 6 Click Multivalent Glycomaterials: Glycoclusters, Glycodendrimers, Glycopolymers, Hybrid Glycomaterials, and Glycosurfaces 143 Carmen Ortiz Mellet, Alejandro M endez-Ardoy, and Jos e Manuel Garc (c)¥a Fern andez 7 Toward Imaging Glycotools by Click Coupling 183 Yves Chapleur, Christine Vala, Franc oise Chr etien, and Sandrine Lamand e-Langle 8 Bioorthogonal Reactions for Labeling Glycoconjugates 211 Fr ed eric Friscourt and Geert-Jan Boons 9 "Sweet" Sucrose Macrocycles via a "Click Chemistry" Route 235 Mykhaylo A. Potopnyk and S(c)(c)awomir Jarosz IV CARBOHYDRATE CLICK CHEMISTRY IN BIOMEDICAL SCIENCES 10 Neoglycoprotein Synthesis Using the Copper-Catalyzed Azide-Alkyne Click Reaction and Native Chemical Ligation 253 Joanna M. Wojnar, Dong Jun Lee, Clive W. Evans, Kalyaneswar Mandal, Stephen B. H. Kent, and Margaret A. Brimble 11 Biomedical Applications of "Click"-Modified Cyclodextrins 271 Zhenshan Jia, Rakesh K. Singh, and Dong Wang 12 Triazolyl Glycoconjugates in Medicinal Chemistry 293 Rama Pati Tripathi, Pratibha Dwivedi, Anindra Sharma, Divya Kushwaha, and Vinod Kumar Tiwari 13 Click Chemistry Applied to Carbohydrate-Based Drug Discovery 325 Vanessa Leiria Campo and Ivone Carvalho INDEX 359
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