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<p>Contributors xv</p> <p>Foreword xix</p> <p>Preface xxiii</p> <p><b>1 Glycochemistry: Overview and Progress 1</b><br /><i>Matthew Schombs and Jacquelyn Gervay?-Hague</i></p> <p>1.1 Introduction, 1</p> <p>1.2 Nomenclature, Structures, and Properties of Sugars, 2</p> <p>1.3 Historical Overview of Carbohydrate Research, 12</p> <p>1.4 Onward to the Twenty?-First Century, 22</p> <p>1.5 Conclusion and Outlook, 28</p> <p>References, 29</p> <p><b>2 Protecting Group Strategies in Carbohydrate Synthesis 35</b><br /><i>Shang?-Cheng Hung and Cheng?-Chung Wang</i></p> <p>2.1 Introduction, 35</p> <p>2.2 General Considerations for Protecting Group Selection, 36</p> <p>2.3 Common Protecting Groups in Carbohydrate Synthesis, 38</p> <p>2.4 Regioselective Protection of Monosaccharides, 46</p> <p>2.5 One?-Pot Protection Methods, 57</p> <p>2.6 Conclusion, 61</p> <p>References, 62</p> <p><b>3 General Aspects in O?-Glycosidic Bond Formation 69</b><br /><i>Xin?-Shan Ye and Weigang Lu</i></p> <p>3.1 Introduction, 69</p> <p>3.2 Some Basic Concepts, 69</p> <p>3.3 Methods for Glycosidic Bond Formation, 74</p> <p>3.4 Glycosylation Strategies, 86</p> <p>3.5 Conclusion, 91</p> <p>References, 91</p> <p><b>4 Controlling Anomeric Selectivity, Reactivity, and Regioselectivity in Glycosylations Using Protecting Groups 97</b><br /><i>Thomas Jan Boltje, Lin Liu, and Geert?-Jan Boons</i></p> <p>4.1 Introduction, 97</p> <p>4.2 Protecting Group and Control of Anomeric Selectivity of Glycosylations, 98</p> <p>4.3 Use of Protecting Groups for Chemoselective Glycosylations, 115</p> <p>4.4 Protecting Groups in Regioselective Glycosylations, 118</p> <p>4.5 Conclusion, 125</p> <p>References, 125</p> <p><b>5 Stereocontrolled Synthesis of Sialosides 131</b><br /><i>Chandrasekhar Navuluri and David Crich</i></p> <p>5.1 Introduction, 131</p> <p>5.2 Conformational Analysis of Sialyl Oxocarbenium Ions, 132</p> <p>5.3 Additives in Sialylations, 133</p> <p>5.4 Leaving Groups in Sialylations, 134</p> <p>5.5 Influence of the N5 Protecting Group on Reactivity and Selectivity, 134</p> <p>5.6 4?-O,5?-N?-Oxazolidinone Group and its Stereodirecting Influence on Sialylations, 139</p> <p>5.7 4,5?-O?-Carbonate Protecting Group in α?-Selective KDN Donors, 144</p> <p>5.8 Other Cyclic and Bicyclic Protecting Systems for Sialyl Donors, 145</p> <p>5.9 Mechanistic Aspects of Sialylation with Cyclically Protected Sialyl Donors, 146</p> <p>5.10 Influence of Hydroxy Protecting Groups on Sialyl Donor Reactivity and Selectivity, 147</p> <p>5.11 Stereoselective C?-Sialoside Formation, 148</p> <p>5.12 Stereoselective S?-Sialoside Formation, 149</p> <p>5.13 Conclusion, 151</p> <p>References, 151</p> <p><b>6 Strategies for One?-Pot Synthesis of Oligosaccharides 155</b><br /><i>Bo Yang, Keisuke Yoshida, and Xuefei Huang</i></p> <p>6.1 Introduction, 155</p> <p>6.2 One?-Pot Glycosylation from the Nonreducing End to the Reducing End, 156</p> <p>6.3 Regioselective One?-Pot Glycosylation: Construction of Oligosaccharides from the Reducing End to the Nonreducing End, 175</p> <p>6.4 Hybrid One?-Pot Glycosylation, 179</p> <p>6.5 Conclusion, 183</p> <p>Acknowledgments, 183</p> <p>References, 183</p> <p><b>7 Automated Oligosaccharide Synthesis: Techniques and Applications 189</b><br /><i>Mattan Hurevich, Jeyakumar Kandasamy, and Peter H. Seeberger</i></p> <p>7.1 Introduction, 189</p> <p>7.2 Challenges and Limitations in Solution?-Phase Oligosaccharide Synthesis, 190</p> <p>7.3 Solid?-Phase Oligosaccharide Synthesis, 191</p> <p>7.4 Automated Oligosaccharide Synthesis, 193</p> <p>7.5 Microfluidic Techniques for Oligosaccharide Synthesis, 199</p> <p>7.6 Conclusion and Outlook, 202</p> <p>Acknowledgments, 202</p> <p>References, 202</p> <p><b>8 Sugar Synthesis by Microfluidic Techniques 205</b><br /><i>Koichi Fukase, Katsunori Tanaka, Yukari Fujimoto, Atsushi Shimoyama, and Yoshiyuki Manabe</i></p> <p>8.1 Introduction, 205</p> <p>8.2 Microfluidic Glycosylation, 206</p> <p>8.3 Conclusion, 216</p> <p>References, 217</p> <p><b>9 Chemoenzymatic Synthesis of Carbohydrates 221</b><br /><i>Kasemsiri Chandarajoti and Jian Liu</i></p> <p>9.1 Introduction, 221</p> <p>9.2 Oligosaccharides and Polysaccharides Produced by GTases, 222</p> <p>9.3 Chemoenzymatic Synthesis of HS, 223</p> <p>9.4 Conclusion, 231</p> <p>References, 231</p> <p><b>10 Synthesis of Glycosaminoglycans 235</b><br /><i>Medel Manuel L. Zulueta, Shu?-Yi Lin, Yu?-Peng Hu, and Shang?-Cheng Hung</i></p> <p>10.1 Introduction, 235</p> <p>10.2 General Strategies, 238</p> <p>10.3 Synthesis of Derivatives of l?-Idose and IdoA, 240</p> <p>10.4 Synthesis via Stepwise Solution?-Phase Assembly and Compound Diversification, 242</p> <p>10.5 Synthesis via Solution?-Phase One?-Pot Assembly, 250</p> <p>10.6 Polymer?-Supported Synthesis and Automation, 253</p> <p>10.7 GAG Mimetics, 256</p> <p>10.8 Conclusion, 257</p> <p>References, 258</p> <p><b>11 Chemical Glycoprotein Synthesis 263</b><br /><i>Yasuhiro Kajihara, Masumi Murakami, and Carlo Unverzagt</i></p> <p>11.1 Introduction, 263</p> <p>11.2 Oligosaccharide Structures, 264</p> <p>11.3 Biosynthesis of Glycoproteins, 265</p> <p>11.4 Chemical Protein Synthesis, 267</p> <p>11.5 Synthesis of Glycopeptides, 269</p> <p>11.6 Synthesis of Glycopeptide?-αthioesters, 270</p> <p>11.7 Chemical Synthesis of Glycoproteins, 275</p> <p>11.8 Conclusion, 288</p> <p>References, 288</p> <p><b>12 Synthesis of Glycosphingolipids 293</b><br /><i>Suvarn S. Kulkarni</i></p> <p>12.1 Introduction, 293</p> <p>12.2 Classification and Nomenclature of GSLs, 294</p> <p>12.3 Biological Significance of GSLs, 296</p> <p>12.4 Synthesis of GSLs, 297</p> <p>12.5 Conclusion, 320</p> <p>References, 320</p> <p><b>13 Synthesis of Glycosylphosphatidylinositol Anchors 327</b><br /><i>Charles Johnson and Zhongwu Guo</i></p> <p>13.1 Introduction, 327</p> <p>13.2 Synthesis of the Tryp. brucei GPI Anchor, 328</p> <p>13.3 Synthesis of the Yeast GPI Anchor, 333</p> <p>13.4 Synthesis of the Rat Brain Thy?-1 GPI Anchor, 335</p> <p>13.5 Synthesis of Plasmodium falciparum GPI Anchor, 340</p> <p>13.6 Synthesis of Trypanosoma cruzi GPI Anchor, 344</p> <p>13.7 Synthesis of a Human Sperm CD52 Antigen GPI Anchor, 349</p> <p>13.8 Synthesis of a Human Lymphocyte CD52 Antigen GPI Anchor, 351</p> <p>13.9 Synthesis of the Branched GPI Anchor of Toxoplasma gondii, 354</p> <p>13.10 Conclusion, 355</p> <p>Acknowledgment, 356</p> <p>References, 357</p> <p><b>14 Synthesis of Bacterial Cell Envelope Components 361</b><br /><i>Akihiro Ishiwata and Yukishige Ito</i></p> <p>14.1 Introduction, 361</p> <p>14.2 Peptidoglycan and Related Glycoconjugates, 362</p> <p>14.3 LPS and Related Glycoconjugates, 371</p> <p>14.4 Lipoteichoic Acid, 380</p> <p>14.5 Mycolyl Arabinogalactan, LAM, and Related Glycoconjugates, 382</p> <p>14.6 Oligosaccharides of Bacterial Glycoprotein and Related Glycoconjugates, 390</p> <p>14.7 Conclusion, 394</p> <p>References, 395</p> <p><b>15 Discoveries and Applications of Glycan Arrays 407</b><br /><i>Chung?-Yi Wu and Shih?-Huang Chang</i></p> <p>15.1 Introduction, 407</p> <p>15.2 Discoveries of Glycan Arrays, 407</p> <p>15.3 Applications of Glycan Array, 412</p> <p>15.4 Conclusion, 418</p> <p>References, 418</p> <p><b>16 Synthesis and Applications of Glyconanoparticles, Glycodendrimers, and Glycoclusters in Biological Systems 425</b><br /><i>Avijit Kumar Adak, Ching?-Ching Yu, and Chun?-Cheng Lin</i></p> <p>16.1 Introduction, 425</p> <p>16.2 Significance of Multivalent Binding Interactions in Biological Systems, 426</p> <p>16.3 Glyconanoparticles, Glycodendrimers, and Glycoclusters: General Overview, 428</p> <p>16.4 Plant Lectins, 431</p> <p>16.5 AB5 Toxins, 438</p> <p>16.6 Bacterial Adhesion Lectins, 440</p> <p>16.7 Influenza Virus, 445</p> <p>16.8 Detection of Bacteria, 445</p> <p>16.9 Glyco?-MNPs as Nanoprobes for Labeling Cells and Magnetic Resonance Imaging Agents, 446</p> <p>16.10 Cyclopeptide?-Based Glycoclusters as Vaccine Adjuvants, 447</p> <p>16.11 Conclusion, 449</p> <p>Acknowledgments, 449</p> <p>References, 450</p> <p><b>17 Design and Synthesis of Carbohydrates and Carbohydrate Mimetics as Anti?-Influenza Agents 455</b><br /><i>Mauro Pascolutti and Mark von Itzstein</i></p> <p>17.1 Introduction, 455</p> <p>17.2 Influenza Viruses, 456</p> <p>17.3 Development of Anti?-Influenza Therapeutics, 459</p> <p>17.4 Sialic Acid: The Viral Cell?-Surface Receptor Ligand, 460</p> <p>17.5 Hemagglutinin, 460</p> <p>17.6 Sialidase, 461</p> <p>17.7 Influenza Virus Sialidase as a Drug Discovery Target, 464</p> <p>17.8 Structural Differences Recently Identified in Influenza a Virus Sialidase Subtypes, 471</p> <p>17.9 New Influenza Virus Sialidase Inhibitors Targeting the 150?-Cavity, 473</p> <p>References, 476</p> <p><b>18 Design and Synthesis of Ligands and Antagonists of Siglecs as Immune Response Modifiers 483</b><br /><i>Hajjaj H. M. Abdu?-Allah, Hideharu Ishida, and Makoto Kiso</i></p> <p>18.1 Introduction, 483</p> <p>18.2 Lectins, 484</p> <p>18.3 Siglecs, 484</p> <p>18.4 Siglecs and Innate Immunity, 489</p> <p>18.5 Design and Synthesis of High?-Affinity Ligands for Siglecs, 494</p> <p>18.6 Conclusion and Future Directions, 501</p> <p>References, 502</p> <p><b>19 Sugar–Protein Hybrids for Biomedical Applications 509</b><br /><i>Macarena Sánchez?-Navarro and Benjamin G. Davis</i></p> <p>19.1 Introduction, 509</p> <p>19.2 Challenges in the Development of Glycoprotein?-Based Therapeutics, 510</p> <p>19.3 Why Unnatural? 510</p> <p>19.4 Retrosynthetic Analysis, 511</p> <p>19.5 Linkages, 512</p> <p>19.6 Glycoprotein?-Based Therapeutics, 521</p> <p>19.7 Conclusion, 527</p> <p>References, 527</p> <p>Index 535</p>

<p><b>Shang-Cheng Hung, PhD,</b> 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. <br /> <br /> <b>Medel Manuel L. Zulueta, PhD</b>, 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.</p>

<p>Glycans – biomolecules that are often conjugated with carbohydrates – modulate processes like cancer progression, immune response and cell-to-cell communication. However, deciphering their molecular processes is difficult because carbohydrates have complex structures and the variety in their assembly and syntheses has always been challenging. There have been many advances over the past couple of decades in glycochemistry that reduce time and material lost during purification and procedures. With new technologies and updated techniques in the field, scientists continue to better understand the role of sugars, especially in applications like drug development, candidate vaccine preparations, and probing mechanisms in living systems. As research sheds more light on the field of glycochemistry, the advances also become more available and useful to general chemists and biologists.</p> <p>Offering a comprehensive and concise review on principles, strategies, and crucial advances in glycochemistry; <i>Glycochemical Synthesis: Strategies and Applications</i> emphasizes the advances and updates from the last few years and illustrates them with key examples. It begins with fundamental synthetic aspects and expands to specific solutions to challenges in oligosaccharide assembly, strategies to the design and synthesis of sugars, techniques in the preparation of glycoconjugates, and the contributions of carbohydrate synthesis to understanding structure–activity relationships and multivalency.</p> <p>A valuable and complete reference about techniques and synthetic design for a major class of biomolecule, <i>Glycochemical Synthesis</i> offers a number of key benefits that include:</p> <p>•          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</p> <p>•          Discussion of practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development</p> <p>•          A comprehensive and concise resource for readers interested in synthetic carbohydrate chemistry</p>

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