Description
Book SynopsisLays 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 resultin
Table of Contents
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´©¥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©©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
