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:
* Click chemistry strategies and decoupling
* Thio-click chemistry of carbohydrates
* Carbohydrate click chemistry for novel synthetic targets
* Carbohydrate click chemistry in biomedical sciences
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.
Зміст
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 Sawomir 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
Про автора
ZBIGNIEW J. WITCZAK, Ph D, 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, Ph D, 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.
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