Glycochemical Synthesis: Strategies and Applications

Glycochemical Synthesis: Strategies and Applications

By: Medel Manuel L. Zulueta (editor), Shang-Cheng Hung (editor)Hardback

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Description

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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About Author

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.

Contents

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 -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 Synthesis by Microfluidic Techniques 205 Koichi Fukase, Katsunori Tanaka, Yukari Fujimoto, Atsushi Shimoyama, and Yoshiyuki Manabe 8.1 Introduction, 205 8.2 Microfluidic Glycosylation, 206 8.3 Conclusion, 216 References, 217 9 Chemoenzymatic Synthesis of Carbohydrates 221 Kasemsiri Chandarajoti and Jian Liu 9.1 Introduction, 221 9.2 Oligosaccharides and Polysaccharides Produced by GTases, 222 9.3 Chemoenzymatic Synthesis of HS, 223 9.4 Conclusion, 231 References, 231 10 Synthesis of Glycosaminoglycans 235 Medel Manuel L. Zulueta, Shu -Yi Lin, Yu -Peng Hu, and Shang -Cheng Hung 10.1 Introduction, 235 10.2 General Strategies, 238 10.3 Synthesis of Derivatives of l -Idose and IdoA, 240 10.4 Synthesis via Stepwise Solution -Phase Assembly and Compound Diversification, 242 10.5 Synthesis via Solution -Phase One -Pot Assembly, 250 10.6 Polymer -Supported Synthesis and Automation, 253 10.7 GAG Mimetics, 256 10.8 Conclusion, 257 References, 258 11 Chemical Glycoprotein Synthesis 263 Yasuhiro Kajihara, Masumi Murakami, and Carlo Unverzagt 11.1 Introduction, 263 11.2 Oligosaccharide Structures, 264 11.3 Biosynthesis of Glycoproteins, 265 11.4 Chemical Protein Synthesis, 267 11.5 Synthesis of Glycopeptides, 269 11.6 Synthesis of Glycopeptide - thioesters, 270 11.7 Chemical Synthesis of Glycoproteins, 275 11.8 Conclusion, 288 References, 288 12 Synthesis of Glycosphingolipids 293 Suvarn S. Kulkarni 12.1 Introduction, 293 12.2 Classification and Nomenclature of GSLs, 294 12.3 Biological Significance of GSLs, 296 12.4 Synthesis of GSLs, 297 12.5 Conclusion, 320 References, 320 13 Synthesis of Glycosylphosphatidylinositol Anchors 327 Charles Johnson and Zhongwu Guo 13.1 Introduction, 327 13.2 Synthesis of the Tryp. brucei GPI Anchor, 328 13.3 Synthesis of the Yeast GPI Anchor, 333 13.4 Synthesis of the Rat Brain Thy -1 GPI Anchor, 335 13.5 Synthesis of Plasmodium falciparum GPI Anchor, 340 13.6 Synthesis of Trypanosoma cruzi GPI Anchor, 344 13.7 Synthesis of a Human Sperm CD52 Antigen GPI Anchor, 349 13.8 Synthesis of a Human Lymphocyte CD52 Antigen GPI Anchor, 351 13.9 Synthesis of the Branched GPI Anchor of Toxoplasma gondii, 354 13.10 Conclusion, 355 Acknowledgment, 356 References, 357 14 Synthesis of Bacterial Cell Envelope Components 361 Akihiro Ishiwata and Yukishige Ito 14.1 Introduction, 361 14.2 Peptidoglycan and Related Glycoconjugates, 362 14.3 LPS and Related Glycoconjugates, 371 14.4 Lipoteichoic Acid, 380 14.5 Mycolyl Arabinogalactan, LAM, and Related Glycoconjugates, 382 14.6 Oligosaccharides of Bacterial Glycoprotein and Related Glycoconjugates, 390 14.7 Conclusion, 394 References, 395 15 Discoveries and Applications of Glycan Arrays 407 Chung -Yi Wu and Shih -Huang Chang 15.1 Introduction, 407 15.2 Discoveries of Glycan Arrays, 407 15.3 Applications of Glycan Array, 412 15.4 Conclusion, 418 References, 418 16 Synthesis and Applications of Glyconanoparticles, Glycodendrimers, and Glycoclusters in Biological Systems 425 Avijit Kumar Adak, Ching -Ching Yu, and Chun -Cheng Lin 16.1 Introduction, 425 16.2 Significance of Multivalent Binding Interactions in Biological Systems, 426 16.3 Glyconanoparticles, Glycodendrimers, and Glycoclusters: General Overview, 428 16.4 Plant Lectins, 431 16.5 AB5 Toxins, 438 16.6 Bacterial Adhesion Lectins, 440 16.7 Influenza Virus, 445 16.8 Detection of Bacteria, 445 16.9 Glyco -MNPs as Nanoprobes for Labeling Cells and Magnetic Resonance Imaging Agents, 446 16.10 Cyclopeptide -Based Glycoclusters as Vaccine Adjuvants, 447 16.11 Conclusion, 449 Acknowledgments, 449 References, 450 17 Design and Synthesis of Carbohydrates and Carbohydrate Mimetics as Anti -Influenza Agents 455 Mauro Pascolutti and Mark von Itzstein 17.1 Introduction, 455 17.2 Influenza Viruses, 456 17.3 Development of Anti -Influenza Therapeutics, 459 17.4 Sialic Acid: The Viral Cell -Surface Receptor Ligand, 460 17.5 Hemagglutinin, 460 17.6 Sialidase, 461 17.7 Influenza Virus Sialidase as a Drug Discovery Target, 464 17.8 Structural Differences Recently Identified in Influenza a Virus Sialidase Subtypes, 471 17.9 New Influenza Virus Sialidase Inhibitors Targeting the 150 -Cavity, 473 References, 476 18 Design and Synthesis of Ligands and Antagonists of Siglecs as Immune Response Modifiers 483 Hajjaj H. M. Abdu -Allah, Hideharu Ishida, and Makoto Kiso 18.1 Introduction, 483 18.2 Lectins, 484 18.3 Siglecs, 484 18.4 Siglecs and Innate Immunity, 489 18.5 Design and Synthesis of High -Affinity Ligands for Siglecs, 494 18.6 Conclusion and Future Directions, 501 References, 502 19 Sugar Protein Hybrids for Biomedical Applications 509 Macarena Sanchez -Navarro and Benjamin G. Davis 19.1 Introduction, 509 19.2 Challenges in the Development of Glycoprotein -Based Therapeutics, 510 19.3 Why Unnatural? 510 19.4 Retrosynthetic Analysis, 511 19.5 Linkages, 512 19.6 Glycoprotein -Based Therapeutics, 521 19.7 Conclusion, 527 References, 527 Index 535

Product Details

  • publication date: 05/09/2013
  • ISBN13: 9781118299845
  • Format: Hardback
  • Number Of Pages: 576
  • ID: 9781118299845
  • weight: 920
  • ISBN10: 1118299841

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