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Click Chemistry in Glycoscience
New Developments and Strategies
Zbigniew J. Witczak (Author), Roman Bielski (Author), Derek Horton (Foreword by)
9781118275337, Wiley
Hardback, published 12 April 2013
400 pages
23.6 x 16 x 3 cm, 0.771 kg
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: 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.
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 II THIO-CLICK CHEMISTRY OF CARBOHYDRATES 2 Thio-Click Chemistry in Glycoscience: Overview and Perspectives 33 3 Free-Radical Thiol-ene and Thiol-yne Couplings as Click Processes for Glycoconjugation 45 III CARBOHYDRATE CLICK CHEMISTRY FOR NOVEL SYNTHETIC TARGETS 4 The Development and Application of Clickable Lipid Analogs for Elucidating and Harnessing Lipid Functions 79 5 Clicking Sugars onto Sugars: Oligosaccharide Analogs and Glycoclusters on Carbohydrate Scaffolds 107 6 Click Multivalent Glycomaterials: Glycoclusters, Glycodendrimers, Glycopolymers, Hybrid Glycomaterials, and Glycosurfaces 143 7 Toward Imaging Glycotools by Click Coupling 183 8 Bioorthogonal Reactions for Labeling Glycoconjugates 211 9 “Sweet” Sucrose Macrocycles via a “Click Chemistry” Route 235 IV CARBOHYDRATE CLICK CHEMISTRY IN BIOMEDICAL SCIENCES 10 Neoglycoprotein Synthesis Using the Copper-Catalyzed Azide–Alkyne Click Reaction and Native Chemical Ligation 253 11 Biomedical Applications of “Click”-Modified Cyclodextrins 271 12 Triazolyl Glycoconjugates in Medicinal Chemistry 293 13 Click Chemistry Applied to Carbohydrate-Based Drug Discovery 325 INDEX 359
Roman Bielski and Zbigniew J. Witczak
Zbigniew J. Witczak
Alessandro Dondoni and Alberto Marra
Michael D. Best
Maria Laura Uhrig and Jos´e Kovensky
Carmen Ortiz Mellet, Alejandro M´endez-Ardoy, and Jos´e Manuel Garc´©¥a Fern´andez
Yves Chapleur, Christine Vala, Franc¸oise Chr´etien, and Sandrine Lamand´e-Langle
Fr´ed´eric Friscourt and Geert-Jan Boons
Mykhaylo A. Potopnyk and S©©awomir Jarosz
Joanna M. Wojnar, Dong Jun Lee, Clive W. Evans, Kalyaneswar Mandal, Stephen B. H. Kent, and Margaret A. Brimble
Zhenshan Jia, Rakesh K. Singh, and Dong Wang
Rama Pati Tripathi, Pratibha Dwivedi, Anindra Sharma, Divya Kushwaha, and Vinod Kumar Tiwari
Vanessa Leiria Campo and Ivone Carvalho
Subject Areas: Chemistry [PN]
