{"product_id":"glycochemical-synthesis-isbn-9781118299845","title":"Glycochemical Synthesis","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.\u003cbr\u003e\u003cbr\u003e•    Provides detailed discussion on specific topics like oligosaccharide assembly and design of sugars, techniques in glycoconjugate preparation, multivalency, and carbohydrate-based drug design\u003cbr\u003e•    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\u003cbr\u003e•    Discusses practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development \u003cp\u003eContributors xv\u003c\/p\u003e \u003cp\u003eForeword xix\u003c\/p\u003e \u003cp\u003ePreface xxiii\u003c\/p\u003e \u003cp\u003e\u003cb\u003e1 Glycochemistry: Overview and Progress 1\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMatthew Schombs and Jacquelyn Gervay-Hague\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e1.1 Introduction, 1\u003c\/p\u003e \u003cp\u003e1.2 Nomenclature, Structures, and Properties of Sugars, 2\u003c\/p\u003e \u003cp\u003e1.3 Historical Overview of Carbohydrate Research, 12\u003c\/p\u003e \u003cp\u003e1.4 Onward to the Twenty-First Century, 22\u003c\/p\u003e \u003cp\u003e1.5 Conclusion and Outlook, 28\u003c\/p\u003e \u003cp\u003eReferences, 29\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Protecting Group Strategies in Carbohydrate Synthesis 35\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eShang-Cheng Hung and Cheng-Chung Wang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e2.1 Introduction, 35\u003c\/p\u003e \u003cp\u003e2.2 General Considerations for Protecting Group Selection, 36\u003c\/p\u003e \u003cp\u003e2.3 Common Protecting Groups in Carbohydrate Synthesis, 38\u003c\/p\u003e \u003cp\u003e2.4 Regioselective Protection of Monosaccharides, 46\u003c\/p\u003e \u003cp\u003e2.5 One-Pot Protection Methods, 57\u003c\/p\u003e \u003cp\u003e2.6 Conclusion, 61\u003c\/p\u003e \u003cp\u003eReferences, 62\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 General Aspects in O-Glycosidic Bond Formation 69\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eXin-Shan Ye and Weigang Lu\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e3.1 Introduction, 69\u003c\/p\u003e \u003cp\u003e3.2 Some Basic Concepts, 69\u003c\/p\u003e \u003cp\u003e3.3 Methods for Glycosidic Bond Formation, 74\u003c\/p\u003e \u003cp\u003e3.4 Glycosylation Strategies, 86\u003c\/p\u003e \u003cp\u003e3.5 Conclusion, 91\u003c\/p\u003e \u003cp\u003eReferences, 91\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Controlling Anomeric Selectivity, Reactivity, and Regioselectivity in Glycosylations Using Protecting Groups 97\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eThomas Jan Boltje, Lin Liu, and Geert-Jan Boons\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e4.1 Introduction, 97\u003c\/p\u003e \u003cp\u003e4.2 Protecting Group and Control of Anomeric Selectivity of Glycosylations, 98\u003c\/p\u003e \u003cp\u003e4.3 Use of Protecting Groups for Chemoselective Glycosylations, 115\u003c\/p\u003e \u003cp\u003e4.4 Protecting Groups in Regioselective Glycosylations, 118\u003c\/p\u003e \u003cp\u003e4.5 Conclusion, 125\u003c\/p\u003e \u003cp\u003eReferences, 125\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Stereocontrolled Synthesis of Sialosides 131\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eChandrasekhar Navuluri and David Crich\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e5.1 Introduction, 131\u003c\/p\u003e \u003cp\u003e5.2 Conformational Analysis of Sialyl Oxocarbenium Ions, 132\u003c\/p\u003e \u003cp\u003e5.3 Additives in Sialylations, 133\u003c\/p\u003e \u003cp\u003e5.4 Leaving Groups in Sialylations, 134\u003c\/p\u003e \u003cp\u003e5.5 Influence of the N5 Protecting Group on Reactivity and Selectivity, 134\u003c\/p\u003e \u003cp\u003e5.6 4-O,5-N-Oxazolidinone Group and its Stereodirecting Influence on Sialylations, 139\u003c\/p\u003e \u003cp\u003e5.7 4,5-O-Carbonate Protecting Group in α-Selective KDN Donors, 144\u003c\/p\u003e \u003cp\u003e5.8 Other Cyclic and Bicyclic Protecting Systems for Sialyl Donors, 145\u003c\/p\u003e \u003cp\u003e5.9 Mechanistic Aspects of Sialylation with Cyclically Protected Sialyl Donors, 146\u003c\/p\u003e \u003cp\u003e5.10 Influence of Hydroxy Protecting Groups on Sialyl Donor Reactivity and Selectivity, 147\u003c\/p\u003e \u003cp\u003e5.11 Stereoselective C-Sialoside Formation, 148\u003c\/p\u003e \u003cp\u003e5.12 Stereoselective S-Sialoside Formation, 149\u003c\/p\u003e \u003cp\u003e5.13 Conclusion, 151\u003c\/p\u003e \u003cp\u003eReferences, 151\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 Strategies for One-Pot Synthesis of Oligosaccharides 155\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eBo Yang, Keisuke Yoshida, and Xuefei Huang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e6.1 Introduction, 155\u003c\/p\u003e \u003cp\u003e6.2 One-Pot Glycosylation from the Nonreducing End to the Reducing End, 156\u003c\/p\u003e \u003cp\u003e6.3 Regioselective One-Pot Glycosylation: Construction of Oligosaccharides from the Reducing End to the Nonreducing End, 175\u003c\/p\u003e \u003cp\u003e6.4 Hybrid One-Pot Glycosylation, 179\u003c\/p\u003e \u003cp\u003e6.5 Conclusion, 183\u003c\/p\u003e \u003cp\u003eAcknowledgments, 183\u003c\/p\u003e \u003cp\u003eReferences, 183\u003c\/p\u003e \u003cp\u003e\u003cb\u003e7 Automated Oligosaccharide Synthesis: Techniques and Applications 189\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMattan Hurevich, Jeyakumar Kandasamy, and Peter H. Seeberger\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e7.1 Introduction, 189\u003c\/p\u003e \u003cp\u003e7.2 Challenges and Limitations in Solution-Phase Oligosaccharide Synthesis, 190\u003c\/p\u003e \u003cp\u003e7.3 Solid-Phase Oligosaccharide Synthesis, 191\u003c\/p\u003e \u003cp\u003e7.4 Automated Oligosaccharide Synthesis, 193\u003c\/p\u003e \u003cp\u003e7.5 Microfluidic Techniques for Oligosaccharide Synthesis, 199\u003c\/p\u003e \u003cp\u003e7.6 Conclusion and Outlook, 202\u003c\/p\u003e \u003cp\u003eAcknowledgments, 202\u003c\/p\u003e \u003cp\u003eReferences, 202\u003c\/p\u003e \u003cp\u003e\u003cb\u003e8 Sugar Synthesis by Microfluidic Techniques 205\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eKoichi Fukase, Katsunori Tanaka, Yukari Fujimoto, Atsushi Shimoyama, and Yoshiyuki Manabe\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e8.1 Introduction, 205\u003c\/p\u003e \u003cp\u003e8.2 Microfluidic Glycosylation, 206\u003c\/p\u003e \u003cp\u003e8.3 Conclusion, 216\u003c\/p\u003e \u003cp\u003eReferences, 217\u003c\/p\u003e \u003cp\u003e\u003cb\u003e9 Chemoenzymatic Synthesis of Carbohydrates 221\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eKasemsiri Chandarajoti and Jian Liu\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e9.1 Introduction, 221\u003c\/p\u003e \u003cp\u003e9.2 Oligosaccharides and Polysaccharides Produced by GTases, 222\u003c\/p\u003e \u003cp\u003e9.3 Chemoenzymatic Synthesis of HS, 223\u003c\/p\u003e \u003cp\u003e9.4 Conclusion, 231\u003c\/p\u003e \u003cp\u003eReferences, 231\u003c\/p\u003e \u003cp\u003e\u003cb\u003e10 Synthesis of Glycosaminoglycans 235\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMedel Manuel L. Zulueta, Shu-Yi Lin, Yu-Peng Hu, and Shang-Cheng Hung\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e10.1 Introduction, 235\u003c\/p\u003e \u003cp\u003e10.2 General Strategies, 238\u003c\/p\u003e \u003cp\u003e10.3 Synthesis of Derivatives of l-Idose and IdoA, 240\u003c\/p\u003e \u003cp\u003e10.4 Synthesis via Stepwise Solution-Phase Assembly and Compound Diversification, 242\u003c\/p\u003e \u003cp\u003e10.5 Synthesis via Solution-Phase One-Pot Assembly, 250\u003c\/p\u003e \u003cp\u003e10.6 Polymer-Supported Synthesis and Automation, 253\u003c\/p\u003e \u003cp\u003e10.7 GAG Mimetics, 256\u003c\/p\u003e \u003cp\u003e10.8 Conclusion, 257\u003c\/p\u003e \u003cp\u003eReferences, 258\u003c\/p\u003e \u003cp\u003e\u003cb\u003e11 Chemical Glycoprotein Synthesis 263\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eYasuhiro Kajihara, Masumi Murakami, and Carlo Unverzagt\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e11.1 Introduction, 263\u003c\/p\u003e \u003cp\u003e11.2 Oligosaccharide Structures, 264\u003c\/p\u003e \u003cp\u003e11.3 Biosynthesis of Glycoproteins, 265\u003c\/p\u003e \u003cp\u003e11.4 Chemical Protein Synthesis, 267\u003c\/p\u003e \u003cp\u003e11.5 Synthesis of Glycopeptides, 269\u003c\/p\u003e \u003cp\u003e11.6 Synthesis of Glycopeptide-αthioesters, 270\u003c\/p\u003e \u003cp\u003e11.7 Chemical Synthesis of Glycoproteins, 275\u003c\/p\u003e \u003cp\u003e11.8 Conclusion, 288\u003c\/p\u003e \u003cp\u003eReferences, 288\u003c\/p\u003e \u003cp\u003e\u003cb\u003e12 Synthesis of Glycosphingolipids 293\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eSuvarn S. Kulkarni\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e12.1 Introduction, 293\u003c\/p\u003e \u003cp\u003e12.2 Classification and Nomenclature of GSLs, 294\u003c\/p\u003e \u003cp\u003e12.3 Biological Significance of GSLs, 296\u003c\/p\u003e \u003cp\u003e12.4 Synthesis of GSLs, 297\u003c\/p\u003e \u003cp\u003e12.5 Conclusion, 320\u003c\/p\u003e \u003cp\u003eReferences, 320\u003c\/p\u003e \u003cp\u003e\u003cb\u003e13 Synthesis of Glycosylphosphatidylinositol Anchors 327\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eCharles Johnson and Zhongwu Guo\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e13.1 Introduction, 327\u003c\/p\u003e \u003cp\u003e13.2 Synthesis of the Tryp. brucei GPI Anchor, 328\u003c\/p\u003e \u003cp\u003e13.3 Synthesis of the Yeast GPI Anchor, 333\u003c\/p\u003e \u003cp\u003e13.4 Synthesis of the Rat Brain Thy-1 GPI Anchor, 335\u003c\/p\u003e \u003cp\u003e13.5 Synthesis of Plasmodium falciparum GPI Anchor, 340\u003c\/p\u003e \u003cp\u003e13.6 Synthesis of Trypanosoma cruzi GPI Anchor, 344\u003c\/p\u003e \u003cp\u003e13.7 Synthesis of a Human Sperm CD52 Antigen GPI Anchor, 349\u003c\/p\u003e \u003cp\u003e13.8 Synthesis of a Human Lymphocyte CD52 Antigen GPI Anchor, 351\u003c\/p\u003e \u003cp\u003e13.9 Synthesis of the Branched GPI Anchor of Toxoplasma gondii, 354\u003c\/p\u003e \u003cp\u003e13.10 Conclusion, 355\u003c\/p\u003e \u003cp\u003eAcknowledgment, 356\u003c\/p\u003e \u003cp\u003eReferences, 357\u003c\/p\u003e \u003cp\u003e\u003cb\u003e14 Synthesis of Bacterial Cell Envelope Components 361\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eAkihiro Ishiwata and Yukishige Ito\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e14.1 Introduction, 361\u003c\/p\u003e \u003cp\u003e14.2 Peptidoglycan and Related Glycoconjugates, 362\u003c\/p\u003e \u003cp\u003e14.3 LPS and Related Glycoconjugates, 371\u003c\/p\u003e \u003cp\u003e14.4 Lipoteichoic Acid, 380\u003c\/p\u003e \u003cp\u003e14.5 Mycolyl Arabinogalactan, LAM, and Related Glycoconjugates, 382\u003c\/p\u003e \u003cp\u003e14.6 Oligosaccharides of Bacterial Glycoprotein and Related Glycoconjugates, 390\u003c\/p\u003e \u003cp\u003e14.7 Conclusion, 394\u003c\/p\u003e \u003cp\u003eReferences, 395\u003c\/p\u003e \u003cp\u003e\u003cb\u003e15 Discoveries and Applications of Glycan Arrays 407\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eChung-Yi Wu and Shih-Huang Chang\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e15.1 Introduction, 407\u003c\/p\u003e \u003cp\u003e15.2 Discoveries of Glycan Arrays, 407\u003c\/p\u003e \u003cp\u003e15.3 Applications of Glycan Array, 412\u003c\/p\u003e \u003cp\u003e15.4 Conclusion, 418\u003c\/p\u003e \u003cp\u003eReferences, 418\u003c\/p\u003e \u003cp\u003e\u003cb\u003e16 Synthesis and Applications of Glyconanoparticles, Glycodendrimers, and Glycoclusters in Biological Systems 425\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eAvijit Kumar Adak, Ching-Ching Yu, and Chun-Cheng Lin\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e16.1 Introduction, 425\u003c\/p\u003e \u003cp\u003e16.2 Significance of Multivalent Binding Interactions in Biological Systems, 426\u003c\/p\u003e \u003cp\u003e16.3 Glyconanoparticles, Glycodendrimers, and Glycoclusters: General Overview, 428\u003c\/p\u003e \u003cp\u003e16.4 Plant Lectins, 431\u003c\/p\u003e \u003cp\u003e16.5 AB5 Toxins, 438\u003c\/p\u003e \u003cp\u003e16.6 Bacterial Adhesion Lectins, 440\u003c\/p\u003e \u003cp\u003e16.7 Influenza Virus, 445\u003c\/p\u003e \u003cp\u003e16.8 Detection of Bacteria, 445\u003c\/p\u003e \u003cp\u003e16.9 Glyco-MNPs as Nanoprobes for Labeling Cells and Magnetic Resonance Imaging Agents, 446\u003c\/p\u003e \u003cp\u003e16.10 Cyclopeptide-Based Glycoclusters as Vaccine Adjuvants, 447\u003c\/p\u003e \u003cp\u003e16.11 Conclusion, 449\u003c\/p\u003e \u003cp\u003eAcknowledgments, 449\u003c\/p\u003e \u003cp\u003eReferences, 450\u003c\/p\u003e \u003cp\u003e\u003cb\u003e17 Design and Synthesis of Carbohydrates and Carbohydrate Mimetics as Anti-Influenza Agents 455\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMauro Pascolutti and Mark von Itzstein\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e17.1 Introduction, 455\u003c\/p\u003e \u003cp\u003e17.2 Influenza Viruses, 456\u003c\/p\u003e \u003cp\u003e17.3 Development of Anti-Influenza Therapeutics, 459\u003c\/p\u003e \u003cp\u003e17.4 Sialic Acid: The Viral Cell-Surface Receptor Ligand, 460\u003c\/p\u003e \u003cp\u003e17.5 Hemagglutinin, 460\u003c\/p\u003e \u003cp\u003e17.6 Sialidase, 461\u003c\/p\u003e \u003cp\u003e17.7 Influenza Virus Sialidase as a Drug Discovery Target, 464\u003c\/p\u003e \u003cp\u003e17.8 Structural Differences Recently Identified in Influenza a Virus Sialidase Subtypes, 471\u003c\/p\u003e \u003cp\u003e17.9 New Influenza Virus Sialidase Inhibitors Targeting the 150-Cavity, 473\u003c\/p\u003e \u003cp\u003eReferences, 476\u003c\/p\u003e \u003cp\u003e\u003cb\u003e18 Design and Synthesis of Ligands and Antagonists of Siglecs as Immune Response Modifiers 483\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eHajjaj H. M. Abdu-Allah, Hideharu Ishida, and Makoto Kiso\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e18.1 Introduction, 483\u003c\/p\u003e \u003cp\u003e18.2 Lectins, 484\u003c\/p\u003e \u003cp\u003e18.3 Siglecs, 484\u003c\/p\u003e \u003cp\u003e18.4 Siglecs and Innate Immunity, 489\u003c\/p\u003e \u003cp\u003e18.5 Design and Synthesis of High-Affinity Ligands for Siglecs, 494\u003c\/p\u003e \u003cp\u003e18.6 Conclusion and Future Directions, 501\u003c\/p\u003e \u003cp\u003eReferences, 502\u003c\/p\u003e \u003cp\u003e\u003cb\u003e19 Sugar–Protein Hybrids for Biomedical Applications 509\u003c\/b\u003e\u003cbr\u003e\u003ci\u003eMacarena Sánchez-Navarro and Benjamin G. Davis\u003c\/i\u003e\u003c\/p\u003e \u003cp\u003e19.1 Introduction, 509\u003c\/p\u003e \u003cp\u003e19.2 Challenges in the Development of Glycoprotein-Based Therapeutics, 510\u003c\/p\u003e \u003cp\u003e19.3 Why Unnatural? 510\u003c\/p\u003e \u003cp\u003e19.4 Retrosynthetic Analysis, 511\u003c\/p\u003e \u003cp\u003e19.5 Linkages, 512\u003c\/p\u003e \u003cp\u003e19.6 Glycoprotein-Based Therapeutics, 521\u003c\/p\u003e \u003cp\u003e19.7 Conclusion, 527\u003c\/p\u003e \u003cp\u003eReferences, 527\u003c\/p\u003e \u003cp\u003eIndex 535\u003c\/p\u003e \u003cp\u003e\u003cb\u003eShang-Cheng Hung, PhD,\u003c\/b\u003e 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. \u003cbr\u003e \u003cbr\u003e \u003cb\u003eMedel Manuel L. Zulueta, PhD\u003c\/b\u003e, 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.\u003c\/p\u003e \u003cp\u003eGlycans – 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.\u003c\/p\u003e \u003cp\u003eOffering a comprehensive and concise review on principles, strategies, and crucial advances in glycochemistry; \u003ci\u003eGlycochemical Synthesis: Strategies and Applications\u003c\/i\u003e 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.\u003c\/p\u003e \u003cp\u003eA valuable and complete reference about techniques and synthetic design for a major class of biomolecule, \u003ci\u003eGlycochemical Synthesis\u003c\/i\u003e offers a number of key benefits that include:\u003c\/p\u003e \u003cp\u003e•          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\u003c\/p\u003e \u003cp\u003e•          Discussion of practical applications of carbohydrates, like medicine, therapeutics, drug and vaccine development\u003c\/p\u003e \u003cp\u003e•          A comprehensive and concise resource for readers interested in synthetic carbohydrate chemistry\u003c\/p\u003e","brand":"Wiley","offers":[{"title":"Default Title","offer_id":47989300920549,"sku":"NP9781118299845","price":218.95,"currency_code":"USD","in_stock":false}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/1842\/7735\/files\/9781118299845.jpg?v=1761783579","url":"https:\/\/k12savings.com\/es\/products\/glycochemical-synthesis-isbn-9781118299845","provider":"K12savings","version":"1.0","type":"link"}