Glycochemical Synthesis (eBook, ePUB)

Strategies and Applications
Redaktion: Hung, Shang-Cheng; Zulueta, Medel Manuel L.

• Format: ePub

Produktbeschreibung

This book is a comprehensive and concise review on principles, strategies, and crucial advances in glycochemistry. It focuses on synthesis and practical applications and emphasizes state-of-the-art approaches to the assembly and design of sugars. Provides detailed discussion on specific topics like oligosaccharide assembly and design of sugars, techniques in glycoconjugate preparation, multivalency, and carbohydrate-based drug design Uses notable examples, like solution-based one-pot methods and automated methods for sugar assembly, to illustrate important concepts and advances in a rapidly emerging field Discusses practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development

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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 576
• Erscheinungstermin: 12. September 2016
• Englisch
• ISBN-13: 9781119006473
• Artikelnr.: 45971043

Autorenporträt

Shang-Cheng Hung, PhD, is a Distinguished Research Fellow of the Genomics Research Center, Academia Sinica, Taiwan. His work focuses on carbohydrate chemistry and chemical biology, including the development of novel approaches to glycan synthesis and the acquisition of important cell-surface glycan components together with their biological evaluations. Medel Manuel L. Zulueta, PhD, is a carbohydrate chemist at the Genomics Research Center, Academia Sinica, Taiwan. He develops of strategies for the chemical synthesis of oligosaccharides, particularly heparin and heparan sulfate.

Inhaltsangabe

Contributors xv

Foreword xix

Preface xxiii

1 Glycochemistry: Overview and Progress 1
Matthew Schombs and Jacquelyn Gervay?-Hague

1.1 Introduction, 1

1.2 Nomenclature, Structures, and Properties of Sugars, 2

1.3 Historical Overview of Carbohydrate Research, 12

1.4 Onward to the Twenty?-First Century, 22

1.5 Conclusion and Outlook, 28

References, 29

2 Protecting Group Strategies in Carbohydrate Synthesis 35
Shang?-Cheng Hung and Cheng?-Chung Wang

2.1 Introduction, 35

2.2 General Considerations for Protecting Group Selection, 36

2.3 Common Protecting Groups in Carbohydrate Synthesis, 38

2.4 Regioselective Protection of Monosaccharides, 46

2.5 One?-Pot Protection Methods, 57

2.6 Conclusion, 61

References, 62

3 General Aspects in O?-Glycosidic Bond Formation 69
Xin?-Shan Ye and Weigang Lu

3.1 Introduction, 69

3.2 Some Basic Concepts, 69

3.3 Methods for Glycosidic Bond Formation, 74

3.4 Glycosylation Strategies, 86

3.5 Conclusion, 91

References, 91

4 Controlling Anomeric Selectivity, Reactivity, and Regioselectivity in Glycosylations Using Protecting Groups 97
Thomas Jan Boltje, Lin Liu, and Geert?-Jan Boons

4.1 Introduction, 97

4.2 Protecting Group and Control of Anomeric Selectivity of Glycosylations, 98

4.3 Use of Protecting Groups for Chemoselective Glycosylations, 115

4.4 Protecting Groups in Regioselective Glycosylations, 118

4.5 Conclusion, 125

References, 125

5 Stereocontrolled Synthesis of Sialosides 131
Chandrasekhar Navuluri and David Crich

5.1 Introduction, 131

5.2 Conformational Analysis of Sialyl Oxocarbenium Ions, 132

5.3 Additives in Sialylations, 133

5.4 Leaving Groups in Sialylations, 134

5.5 Influence of the N5 Protecting Group on Reactivity and Selectivity, 134

5.6 4?-O,5?-N?-Oxazolidinone Group and its Stereodirecting Influence on Sialylations, 139

5.7 4,5?-O?-Carbonate Protecting Group in alpha?-Selective KDN Donors, 144

5.8 Other Cyclic and Bicyclic Protecting Systems for Sialyl Donors, 145

5.9 Mechanistic Aspects of Sialylation with Cyclically Protected Sialyl Donors, 146

5.10 Influence of Hydroxy Protecting Groups on Sialyl Donor Reactivity and Selectivity, 147

5.11 Stereoselective C?-Sialoside Formation, 148

5.12 Stereoselective S?-Sialoside Formation, 149

5.13 Conclusion, 151

References, 151

6 Strategies for One?-Pot Synthesis of Oligosaccharides 155
Bo Yang, Keisuke Yoshida, and Xuefei Huang

6.1 Introduction, 155

6.2 One?-Pot Glycosylation from the Nonreducing End to the Reducing End, 156

6.3 Regioselective One?-Pot Glycosylation: Construction of Oligosaccharides from the Reducing End to the Nonreducing End, 175

6.4 Hybrid One?-Pot Glycosylation, 179

6.5 Conclusion, 183

Acknowledgments, 183

References, 183

7 Automated Oligosaccharide Synthesis: Techniques and Applications 189
Mattan Hurevich, Jeyakumar Kandasamy, and Peter H. Seeberger

7.1 Introduction, 189

7.2 Challenges and Limitations in Solution?-Phase Oligosaccharide Synthesis, 190

7.3 Solid?-Phase Oligosaccharide Synthesis, 191

7.4 Automated Oligosaccharide Synthesis, 193

7.5 Microfluidic Techniques for Oligosaccharide Synthesis, 199

7.6 Conclusion and Outlook, 202

Acknowledgments, 202

References, 202

8 Sugar Syn