Click Chemistry in Glycoscience
New Developments and Strategies
1. Edition April 2013
400 Pages, Hardcover
Wiley & Sons Ltd
Short Description
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.
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
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.
