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

About the Author

ZBIGNIEW J. WITCZAK, PhD, is Professor in the Departmentof Pharmaceutical Sciences of the Nesbitt School of Pharmacy atWilkes University. He has published over ninety research papers andholds six patents. His research focuses on carbohydrate synthons,including levoglucosenone and L-arabinose, as templates forcarbohydrate-based therapeutics. In 2000, Dr. Witczak was awardedthe Melville L. Wolfrom Award from the ACS Division of CarbohydrateChemistry. ROMAN BIELSKI, PhD, is Senior Scientist at ValueRecovery, Inc., Partner in Cheminnolab, LLC, and Adjunct Professorin the Department of Pharmaceutical Sciences at Wilkes University.His research investigates the origin of homochirality, modificationof carbohydrates, solutions to environmental issues, andsustainability. As part of his achievements, Dr. Bielskico-developed a method of enantiomers' resolution, which might havebeen involved in prebiotic homochirality, since it would notrequire the use of chiral compounds.